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Cross Country USA: Portland to Portland

The Bucket List Trip

We are excited to offer our epic Cross Country USA trip, Portland to Portland, for the 5th straight year. The goal: ambitious. The distance: 3,800 miles. The training: intense. The opportunity: unrivaled. If you're ready for the bike trip-and challenge-of a lifetime, prepare to join Trek Travel on a bicycle tour that stretches from the Pacific to the Atlantic across the northern tier of this beautiful country. On this trip, you'll cross 15 states and climb more than 157,000 feet over the course of 42 riding days—all from the saddle of a top-of-the-line Trek Domane bicycle, the use of which is included in your trip price. Aside from the warm-up ride, your shortest day will be 37 miles and the longest, 126 miles. You'll have 16 days at 100 miles or more and four rest days. Although the challenge and dedication to training is substantial, your Trek Travel guides will be with you every pedal stroke of the way, offering encouragement, mechanical and logistical support, camaraderie, and our renowned Trek Travel guest service. Our signature attention to detail—and exhaustive planning and provisioning—will leave you free to just ride. You'll accomplish more physically in 47 days than most people do in a lifetime!

Ready for our new 2019 trip? See the full trip here»
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47 Days & 46 Nights
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Trip Wows
Ride through the Columbia River Gorge past panoramic viewpoints and breathtaking sights like Bridal Veil Falls and Multnomah Falls
Follow in the footsteps of Lewis and Clark, two of the world’s greatest explorers, as you travel the country like pioneers
Pedal past the eroded buttes, pinnacles and spires of South Dakota’s Badlands National Park
Catch a glimpse of Amish country in action as you make your way through the backroads and small towns of the Midwest
Watch the Fall colors change day by day as you climb through New York’s Adirondack Mountains, Vermont’s Green Mountains and New Hampshire’s White Mountains during New England’s fall foliage season
Watch the Experience
The guides made what would have been a nearly impossible trip into a relatively pleasant one. If there's a cushy way to do this ride, then this is it! 
-Nancy

Dates & Prices

The earlier you book, the greater the rewards

Please note, due to the nature of the hotels on this trip, single occupancy is not guaranteed for 3-5 nights
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There are currently no dates available to book for this trip or it is by request only. Please contact a Trip Consultant for more information on available dates.
Don't see your ideal travel date?
Call us at (866) 464-8735 for custom date availability
Looking for a one of a kind, once in a lifetime experience?
Look no further. All you need to do is pick any open trip date, get your group together and we will do the rest. Private trip pricing is as follows:
  • 10+ Guests Price as advertised*
  • 8-9 Guests +$500 per person to trip price*
  • 6-7 Guests +$1,000 per person to trip price*
  • 4-5 Guests +$1,500 per person to trip price*
  • 2-3 Guests +$2,500 per person to trip price*
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Private pricing is not available on Ride Camp, Race, Special Edition or Cross Country style trips.

Your Trek Travel guides will meet you at the Hotel Lucia (400 SW Broadway, Portland, Oregon) at 9:00 AM on the first day of the trip. Today is the day to get everything in order before embarking on your cross-country odyssey. After a 2-hour shuttle to the town of Astoria, you will enjoy a hearty welcome lunch and brief introductions, and your guides will take time to ensure you a comfortable fit on your bike. We recommend that you have a professional bike fit early in your training for the greatest efficiency and to reduce the risk of injury. Please bring your measurements, as well as your saddle, pedals, personal GPS unit, and any other equipment you would like affixed to your bike to this meeting so your guides can set up your bike to your requirements. Following the bike fit, safety tips and some introductory information, it's time for a short scenic spin from Astoria to Fort Stevens State Park and down to the Pacific Ocean where you can dip your tire into the water to mark the official start of your journey. Use the rest of this ride to warm up your legs and make sure you are comfortable in the saddle. Your warm-up ride will be followed by a social hour and dinner, where your guides will discuss your upcoming adventure in more detail and answer any questions you may have.

Today's Ride:

Astoria to Fort Stevens and Return
Approximately 30 miles with 789 feet of climbing

Today's Date:

August 19

Hotel:

Cannery Pier Hotel

Included Meals:

Lunch | Social Hour | Dinner

Your adventure begins today as you depart Astoria and head for Portland on your first long ride of the trip! It's time to bid farewell to the West Coast and turn east as you ease into your first pedal strokes along Youngs River and through the beautiful and densely forested Clatsop State Forest. As you ride, the enclosed green canopy and winding roads gradually open up to bring you just north of Portland where you will continue southeast on the Scappoose-Vernonia Highway and directly into downtown Portland. Explore one of America's most bike-friendly cities this evening as you relish the feeling of accomplishment from completing your first full day in the saddle.

Today's Ride:

Astoria, OR to Portland, OR
Approximately 97 miles with 4,683 feet of climbing

Today's Date:

August 20

Hotel:

Portland Marriott Downtown Waterfront

Included Meals:

Breakfast | Lunch | Dinner

You'll depart Portland this morning on a network of popular bike trails and lanes. Once in Troutdale, you will ride on the Historic Columbia River Gorge Highway 30 that separates Washington from Oregon. The north side of this 75-mile scenic byway boasts spectacular views of the Columbia River Gorge while the south is blessed with a collection of astonishing waterfalls. Take the time to stop at Columbia Point, one of the most scenic outlooks on the journey, and visit the Vista House which was built as a rest stop for early travelers. Don't miss small hikes along the way to view Latourell Falls, Bridal Veil Falls, and Multnomah Falls, to name just a few. As you finish your ride, don't forget to look out onto the river, as Hood River is renowned as one of the best windsurfing locations in the U.S. Tonight is yours to explore. Take a stroll down Oak Street and dine in one of the many tasty bistros.

Today's Ride:

Portland, OR to Hood River, OR
Approximately 77 miles with 3,750 feet of climbing

Today's Date:

August 21

Hotel:

Hood River Hotel

Included Meals:

Breakfast | Lunch

Depart this windsurfing and mountain-biking hotspot to continue following the Lewis and Clark Trail along the water. Cycle the 5-mile Mosier Twin Tunnels Trail that passes through two climate zones and is bordered by numerous types of foliage and plants. In order to avoid considerable time on the highway, we'll cross the bridge at The Dalles to enter Washington and follow the north side of the river before crossing back into Oregon. Finish the day’s ride winding past rolling ranch lands, and tackling the climbs through Cottonwood Canyon State Park and Recreation Area. We’ll be spending the night in Condon, a proud, century-old farming community nestled between miles of rolling, golden wheat fields in Eastern Oregon. Built in 1920, the historic Hotel Condon offers classic charm with a quaint, “small town America” atmosphere.

Today's Ride:

Hood River, OR to Condon, OR
Approximately 101 miles with 8,302 feet of climbing

Today's Date:

August 22

Hotel:

Hotel Condon or Condon Motel

Included Meals:

Breakfast | Lunch | Dinner

After a hilly start this morning, we'll reach the small town of Heppner, known as the “Gateway to the Blues.” Pedal a short stretch of the Blue Mountain Scenic Byway before gradually descending back towards the Columbia River. Enjoy dinner at Nookie’s restaurant, home of the Hermiston Brewing Company & Tap House. This historic building housed a Plymouth dealership for many years in the early 1940’s, but now offers over 15 beers produced in-house! Spend the night in Hermiston, once known as home of Six Mile House, an old-west hotel that served as a stopover for weary travelers, and is now famous for watermelon farms.

Today's Ride:

Condon, OR to Hermiston, OR
Approximately 93 miles with 4,087 feet of climbing

Today's Date:

August 23

Hotel:

Holiday Inn Express

Included Meals:

Breakfast | Lunch | Dinner

Today is a relatively short ride as we make our way to Washington for the second time. Pedal through high-desert sage and the farmland producing the sweet onions, wheat, and wine that give Walla Walla its flavor. Finish your day at the historic Marcus Whitman hotel. Tonight, venture out to find a cozy wine tasting and dinner of your choice. Walk down the tree-lined streets of downtown for a funky mix of vintage shops, boutiques, cafes, and bookstores.

Today's Ride:

Hermiston, OR to Walla Walla, WA
Approximately 72 miles with 3,575 feet of climbing

Today's Date:

August 24

Hotel:

The Marcus Whitman Hotel

Included Meals:

Breakfast | Lunch

Climb out of Walla Walla on gently rolling hills as you make your way through eastern Washington's beautiful golden fields of wheat. Today you will work hard to get to Idaho, the third state of your journey, but the effort will be well worth it as you enjoy a long, winding descent into the state alongside the gentle Asotin Creek and the powerful Snake River. Shortly after crossing the border you will find yourself in Lewiston, located at the confluence of the Snake and Clearwater Rivers. Due to a system of locks and dams, Lewiston is accessible by some ocean-going vessels and is the easternmost port on the west coast.

Today's Ride:

Walla Walla, WA to Lewiston, ID
Approximately 99 miles with 4,870 feet of climbing

Today's Date:

August 25

Hotel:

Red Lion Hotel

Included Meals:

Breakfast | Lunch | Dinner

Soon after departing Lewiston you will enter the land of the Nez Perce Native American tribe. Cruise through undulating hills and scattered towns as you uncover this magnificent gateway to the West. The Nez Perce have made this area home since before the history of the West was recorded with many areas to hunt, fish, hike, and farm. Enjoy the striking views from the banks of the Clearwater River into the hills above. Tonight, you will stay in a hand-built log cabin on the banks of the free-flowing Middle Fork of the Clearwater. Each cabin has two or three bedrooms and shared living spaces, bathrooms, a fireplace, hot tub, and deck to enjoy with your traveling companions turned cabin mates.

Today's Ride:

Lewiston, ID to Kooskia, ID
Approximately 103 miles with 6,377 feet of climbing

Today's Date:

August 26

Hotel:

River Dance Lodge

Included Meals:

Breakfast | Lunch | Dinner

Today you get to conquer Lolo Pass, your first of the Rocky Mountains! You'll follow historic Route 12 as it winds alongside the Lochsa River which is lined by the majestic pines of the Clearwater National Forest. This historic route is a very gentle climb until the last few miles, which greet you with steeper terrain and sweeping views. You'll top out at 5,225 feet when you reach the Montana border. Say hello to state number four and a new time zone! All that's left is a short descent to the Lodge at Lolo Hot Springs. It's a great place to rest and soak your legs after the day's climb.

Today's Ride:

Kooskia, ID to Lolo, MT
Approximately 92 miles with 5,614 feet of climbing

Today's Date:

August 27

Hotel:

The Lodge at Lolo Hot Springs

Included Meals:

Breakfast | Lunch | Dinner

Enjoy a lazy morning with your fellow riders as you get used to the time change, because this short day is nearly all downhill! Today you finish descending the gorgeous, winding road from Lolo Pass into the town of Missoula—home of the University of Montana. Take a look around at the peaks dominating the horizon, as this town lies at the convergence of five separate mountain ranges. It's your choice for lunch so enjoy your favorite foods as you soak in the scene in this fun college town. Tonight you will gather for a social hour and dinner at a favorite local hot spot, as you raise a glass to congratulate each other on reaching your first well-earned rest day and bid farewell to those riders who leave us tomorrow.

Today's Ride:

Lolo, MT to Missoula, MT
Approximately 37 miles with 655 feet of climbing

Today's Date:

August 28

Hotel:

DoubleTree Hotel Missoula - Edgewater

Included Meals:

Breakfast | Lunch | Social Hour | Dinner

Your first rest day has arrived and you’ve certainly earned it! Today is a day to relax, put up your feet, and enjoy. Benefit from a recovery stroll along the trail beside the Clark Fork River or explore the quaint downtown. This could also be the day to get some shopping done as Montana levies no state sales tax! Alternatively, catch up on some sleep, unwind, and simply get some correspondence and laundry done. Today is yours to explore, dine, and recover as you please.

Today's Date:

August 29

Hotel:

DoubleTree Hotel Missoula - Edgewater

Included Meals:

Breakfast

Saddle up! Today you'll take advantage of your well-rested legs to tackle the longest ride of your journey as you continue across the fourth largest state in America. Follow the Blackfoot River out to the plains and enjoy the cool breeze as it wicks down the surrounding mountains and stirs the wildlife below. Keep a careful eye on the sky and passing fields to catch a glance of a bald eagle, mule deer, antelope, elk, or maybe even a grizzly bear. You'll climb to the top of Flesher Pass at 6,131 feet before enjoying a gradual descent into Montana's capital city for the evening.

Today's Ride:

Missoula, MT to Helena, MT
Approximately 125 miles with 5,628 feet of climbing

Today's Date:

August 30

Hotel:

Doubletree by Hilton Helena Downtown

Included Meals:

Breakfast | Lunch | Dinner

Another picturesque day of riding awaits as you start out along the Missouri River and work your way south through Big Sky Country toward Bozeman. As you reach your day's destination, glance east to the Bridger and Bangtail Mountain ranges. These two ranges, separated by Bridger Canyon, were once home to a pair of bickering brothers who pastured horses. Their constant quarreling over which horses belonged to whom made one brother decide to "bang," or cut short, his horse's tails to identify them, and so the name was born. Tonight, you'll stay at a one-of-a-kind hotel in the heart of downtown Bozeman. Enjoy a post-ride snack from the Victory Taco food truck parked outside the hotel before exploring and finding the perfect dinner spot. Be sure to stop at Bangtail Bikes for more stories of the area and to talk to the long-time owner.

Today's Ride:

Helena, MT to Bozeman, MT
Approximately 120 miles with 4,144 feet of climbing

Today's Date:

August 31

Hotel:

The Lark

Included Meals:

Breakfast | Lunch

Today's big ride takes you along the Yellowstone River and the northern border of Yellowstone National Park. Continue to soak up the majestic peaks and rolling fields of the Rocky Mountains on your last full day in Montana. At this point you are surrounded by six different mountain ranges including Beartooth Mountain Range—home to the highest peak in the state, Granite Peak (12,799 ft).

Today's Ride:

Bozeman, MT to Columbus, MT
Approximately 111 miles with 2,881 feet of climbing

Today's Date:

September 1

Hotel:

Super 8 Columbus

Included Meals:

Breakfast | Lunch | Dinner

Travel south this morning to bid farewell to Montana and cross the border into your fifth state: Wyoming. After passing over the Yellowstone River and departing the fisherman's paradise of Columbus, you will begin to discover the second-least densely populated state in the United States. Don't let these grasslands deceive you though: wildlife such as bald eagles, buffalo, and antelope abound in this area of the Wild West. End your day by crossing the Shoshone River and settling in at the foot of the Bighorn Mountains. Tonight, enjoy a good ole fashioned BBQ prepared by your guides in this quiet little town (that all but shuts down for Labor Day) as you prepare yourself for tomorrow's big climb.

Today's Ride:

Columbus, MT to Lovell, WY
Approximately 90 miles with 2,627 feet of climbing

Today's Date:

September 2

Hotel:

Horseshoe Bend Motel

Included Meals:

Breakfast | Lunch | Dinner

Today promises to be a memorable and momentous day, as you will ascend to Observation Point, which, at 9,430 feet, is the highest point of your epic journey. The morning will begin with a leisurely 20 miles of warm-up terrain. Look for the pelicans as you cross the Bighorn River, and get ready to start the toughest climb of the trip. The path you will follow, known as “The Medicine Wheel Passage,” twists up, up and up for 20 miles (and plenty of double-digit gradients) through the Bighorn National Forest. Take a moment to congratulate yourself at the top and enjoy the views of the high mountain meadows before you begin the gradual descent to lunch at Moose Crossing Restaurant. If you keep your eyes open today, you may spot marmot, moose, or if you're very lucky, bighorn sheep. After lunch, enjoy a fabulous and picturesque winding descent into the quintessential ranching town of Sheridan.

Today's Ride:

Lovell, WY to Sheridan, WY
Approximately 99 miles with 7,732 feet of climbing

Today's Date:

September 3

Hotel:

Historic Sheridan Inn

Included Meals:

Breakfast | Lunch | Dinner

As you pedal away from Sheridan, it's easy to imagine the Old West battles and shootouts that once took place here. In fact, just north of here is the site of the Battle of the Little Bighorn where General Custer was killed. Ride like the wind through the vast open countryside, but don't blink as you pass Spotted Horse (population: 2). In fact, be sure to stop in at the Spotted Horse Bar for a Coke and a photo op. Then press onward and you'll find yourself in Gillette, also known as the "Energy Capital of the Nation," home to plenty of natural resources that made this town a center of the oil and gas industry. With views of Eagle Butte Mine along the way, you can see some of the pits from which Wyoming supplies 35% of the nation's coal.

Today's Ride:

Sheridan, WY to Gillette, WY
Approximately 108 miles with 4,753 feet of climbing

Today's Date:

September 4

Hotel:

Hampton Inn Gillette

Included Meals:

Breakfast | Lunch | Dinner

You have worked hard and today it pays off! You can opt for the "short" 75 mile route to the hotel, or for those who just cannot resist seeing all of the sights, you can add on a few miles for striking views of Devil's Tower National Monument. Stop at the marked viewpoint for the perfect photo op or descend all the way to the Visitor's Center and hike around Devil's Tower. Be warned, this is an out-and-back so once you take in the views, you have to climb right back up to the main road. As you make your way on towards Sundance, WY, you continue to pedal over rolling climbs and descents that remind you that you are still in the West. This town may ring a bell, as it is where "The Sundance Kid" got his name after being released from jail here. Stop by the courthouse and see his statue. You can also visit the Crook County Museum to see where his trial took place and learn more about the legends of the old West.

Today's Ride:

Gillette, WY to Sundance, WY
Approximately 90 miles with 4,739 feet of climbing

Today's Date:

September 5

Hotel:

Best Western

Included Meals:

Breakfast | Lunch | Dinner

The northern Black Hills of South Dakota, state number six, await you today. As you ride among the Ponderosa pines of this region, you will discover how the hills received their name. These trees absorb so much of the light, they make the area look practically black. This is another challenging but gorgeous day of riding. As you climb the serene and scenic Spearfish Canyon, where the final scenes of "Dances with Wolves" were filmed, you'll pass close to the famous historic Old West town of Deadwood before descending your way into Rapid City.

Today's Ride:

Sundance, WY to Rapid City, SD
Approximately 103 miles with 6,198 feet of climbing

Today's Date:

September 6

Hotel:

Hotel Alex Johnson

Included Meals:

Breakfast | Lunch | Social Hour | Dinner

Your second rest day is here! Today is your day to rest, recover and celebrate that your hard work has now taken you across 40% of the country! Activities abound to occupy your time in Rapid City. Take this opportunity to visit the eye-catching Mount Rushmore National Monument and Crazy Horse Monument. Or maybe stay closer to town check out the enormous sculptures at Dinosaur Park, walk the imaginative Art Alley or perhaps quiz each other on the Presidential statues located on the street corners of downtown. Whatever you do, don't forget to kick back for a time and enjoy your accomplishments on reaching this milestone!

Today's Date:

September 7

Hotel:

Hotel Alex Johnson

Included Meals:

Breakfast

Back in the saddle and well-rested, today you will venture into Wall, SD, home the famous Wall Drug, a strip mall consisting of restaurants, gift shops, and drug stores. You can't miss it, as you undoubtedly have seen billboards for "5 cent coffee" for several days now. Please note that today includes a stretch of three miles and another of 25 miles on Interstate 90 before reaching Wall. While we strive to avoid interstate riding, it is unavoidable due to the nature of the roads in this area. You may certainly opt to shuttle these sections. After a picnic (and a stop at Wall Drug, of course), you will ride into Badlands National Park. Take your time and soak up the scenery as you wind your way through this unparalleled land of buttes and spires. It was used by many Native Americans as hunting grounds as well as a place to live, with the higher areas perfect as lookouts to see oncoming enemies or herds of animals. Be sure to look for antelope, pronghorns and big horn sheep as you pedal through the park.

Today's Ride:

Rapid City, SD to Kadoka, SD
Approximately 113 miles with 4,014 feet of climbing

Today's Date:

September 8

Hotel:

America’s Best Value Inn Kadoka

Included Meals:

Breakfast | Lunch | Dinner

Today you leave this gateway to the Badlands and Black Hills to continue your journey across the grasslands of South Dakota. This area, including Fort Pierre National Grasslands, provides visitors excellent opportunities to camp, hunt, and fish, but for you it provides a steady, straight road past glowing fields of sunflowers and picturesque farms en route to your destination of Oacoma, South Dakota.

Today's Ride:

Kadoka, SD to Oacoma, SD
Approximately 113 miles with 3,218 feet of climbing

Today's Date:

September 9

Hotel:

Baymont Inn & Suites

Included Meals:

Breakfast | Lunch | Dinner

There are two big reasons to celebrate today: you only have to ride 77 miles, and even better, you have pedaled halfway across the United States! Take some time to reflect on your journey thus far as you cross the rushing Missouri River and head into another beautiful day of open grasslands. Relax as you spin your way through these lands that were once occupied by early American settlers working on the railroad, farms, ranches and in the fur trade. And if your legs will allow it, take a short detour and check out Mitchell's biggest attraction: The Corn Palace!

Today's Ride:

Oacoma, SD to Mitchell, SD
Approximately 77 miles with 1,142 feet of climbing

Today's Date:

September 10

Hotel:

Holiday Inn Express

Included Meals:

Breakfast | Lunch | Dinner

Today is another relatively short day in the saddle at a mere 72 miles. Your ride brings you into South Dakota's largest city: Sioux Falls. The location of Sioux Falls, on the banks of the cascading Big Sioux River, has been a site of human habitation since antiquity. This area was first settled by Native Americans who harnessed the water source for agriculture. The land near the water was also held sacred as a burial ground and is still respected as such today. This evening, after enjoying dinner on your own, take a stroll along the river to Falls Park.

Today's Ride:

Mitchell, SD to Sioux Falls, SD
Approximately 72 miles with 1,410 feet of climbing

Today's Date:

September 11

Hotel:

Holiday Inn Sioux Falls - City Centre

Included Meals:

Breakfast | Lunch

Today you’ll bid a fond farewell to South Dakota at mile 16 as you cross the border into Minnesota, the seventh state along your route so far. Today is the longest ride of the trip at 126 miles and it’s relatively flat, so hope for a tailwind. By popular request, we are by-passing the cornfields of Iowa this year and routing you through Minnesota, aka The Land of 10,000 Lakes. You’ll count a few of them today as you break for a picnic near the shore of Lake Okabena in Worthington, pedal past Temperance Lake near Sherburn and end your ride in Fairmont after passing by Budd Lake. Logistics are simple tonight – dine at the hotel restaurant and spend the rest of your time focusing on recovery.

Today's Ride:

Sioux Falls, SD to Fairmont, MN
Approximately 126 miles with 2,088 feet of climbing

Today's Date:

September 12

Hotel:

Holiday Inn Fairmont

Included Meals:

Breakfast | Lunch | Dinner

Did you know that in addition to Scotch tape, Masking tape, Bisquick, and Wheaties, Green Giant vegetables were invented in Minnesota? Well, today is your chance to get a commemorative photo with the Jolly Green Giant himself. The 55.5 feet tall statue was commissioned by Paul Hedberg in 1978. Hedberg, the owner of a local radio station and host of a show called “Welcome Travelers”, gave each of his guests Green Giant vegetables from the local factory as a parting gift. When he learned that I-90 would bypass Blue Earth, he feared he would lose his supply of travelers so he took it upon himself to raise money for the statue in hopes that it would lure tourists to town. While Green Giant no longer owns the local canning plant and the radio show no longer exists, the town’s beloved statue still stands and has spawned a Giant Museum and Giant Days festival. If that’s not enough Americana for you today, be sure to visit the Spam Museum when you get to Austin.

Today's Ride:

Fairmont, MN to Austin, MN
Approximately 81 miles with 1,327 feet of climbing

Today's Date:

September 13

Hotel:

Holiday Inn Austin

Included Meals:

Breakfast | Lunch | Dinner

This morning, say goodbye to the home of Hormel as you make your way across the rest of southern Minnesota. Once again, the ride today is long and relatively flat. The highlight comes about halfway through when you enter the Root River Trail. Enjoy 40 miles of paved bike path as you meander through small towns set on the banks of the Root River. As the path ends, you’ll get a wake-up call in the form of a steep one-mile climb. After a few miles on the plateau, you’ll descend toward the mighty Mississippi River and the border of state number eight: good ole’ Wisconsin. Our home for tonight is The Charmant Hotel, a boutique hotel housed in a renovated candy factory. The name was inspired by a premium line of chocolates once made here. The maple flooring, wooden beams and exposed brick of the original 1898 structure have been preserved, giving this historic hotel a warm, charming appeal. Enjoy the lovely setting with a drink on the rooftop terrace or take a stroll through the park to the banks of the Mississippi River.

Today's Ride:

Austin, MN to La Crosse, WI
Approximately 117 miles with 2,890 feet of climbing

Today's Date:

September 14

Hotel:

The Charmant Hotel

Included Meals:

Breakfast | Lunch | Dinner

Gear up! Today’s ride is anything but flat! You’ll cross the heart of Wisconsin's Driftless Area today. This unglaciated region will surprise and delight you with its diversity. Forested slopes give way to green valleys and dramatic limestone bluffs that have been carved through the ages by crystal clear trout streams. Conquer everything from rollers to short but surprisingly steep hills as you navigate this cycling paradise. Enjoy a hearty picnic lunch mid-ride before forging on toward the quaint town of Spring Green. You will pass Frank Lloyd Wright's famous home, Taliesin, on our way to our home for the evening. Kick back with a post-ride beer by the fire pit. Tonight, you can relax and enjoy a well-earned dinner at our hotel.

Today's Ride:

La Crosse, WI to Spring Green, WI
Approximately 104 miles with 4,585 feet of climbing

Today's Date:

September 15

Hotel:

Spring Valley Inn

Included Meals:

Breakfast | Lunch | Dinner

Today’s ride is relatively short, but jam-packed with great roads. It’s a favorite route of the local Trek Travel team. You’ll sweep through the last hills of the Driftless Area en route to more mellow terrain. Many of the farms you will see along the way are organic and use sustainable growing practices to produce a wide variety of heirloom vegetables and artisanal cheeses found in many of Madison’s restaurants and at its bountiful farmer’s market. Finish this leg strong as you make your way around Lake Mendota and roll into Wisconsin's gorgeous capital city. Since our ride is short today, you'll have a chance to enjoy lunch on your own before we check-in. Then relax and prepare to celebrate with a special evening in Trek Travel's midwestern hometown!

Today's Ride:

Spring Green, WI to Madison, WI
Approximately 55 miles with 2,773 feet of climbing

Today's Date:

September 16

Hotel:

The Madison Concourse Hotel

Included Meals:

Breakfast | Social Hour | Dinner

Congrats on reaching your third rest day! You are now two thirds of the way through the total mileage and elevation of this epic conquest. Opt to spend today touring Trek Bicycle Corporation headquarters or exploring Wisconsin's thriving capital city. Madison has lots to offer when it comes to food, the arts, entertainment and recreational activities. Take a free tour of the Capitol building, one of the most beautiful in the nation. And, don't miss a stroll down State St, the pedestrian street connecting the Capitol to the University of Wisconsin campus. Have a beer at Memorial Union Terrace, a favorite local hangout on the shore of Lake Mendota. Notice the spectacle of more bikes than cars in many sections of town and the plentiful variety of local breweries and outdoor patios for dining. You may also choose to squeeze in a yoga class or a paddle on one of the lakes. Kick back and relax however you see fit--today is your day off.

Today's Date:

September 17

Hotel:

The Madison Concourse Hotel

Included Meals:

Breakfast

Another great day stretches out ahead of you, as you exit Madison via a popular bike path and ease back into small towns and rolling farmland. Enjoy roaming near the scattered lakes and quiet suburbs as you near Milwaukee. You'll pass the home of the Milwaukee Brewers and the Harley Davidson museum before you arrive at the Iron Horse Hotel. Try a game of pool or have a drink in The Yard as you savor this striking warehouse turned hotel. Tonight, dinner is on your own. Choose to stay close to home at The Yard, the hotel's popular outdoor patio, or venture out to the Historic Third Ward.

Today's Ride:

Madison WI, to Milwaukee, WI
Approximately 89 miles with 2,406 feet of climbing

Today's Date:

September 18

Hotel:

The Iron Horse Hotel

Included Meals:

Breakfast | Lunch

Enjoy a leisurely morning before your short ride to the Lake Express ferry terminal. In only two-and-a-half hours this high-speed ferry will take you across the grand waters of Lake Michigan. Upon arrival on the eastern shore, you will be on Eastern Time and enter the ninth state of your journey: Michigan. Feel the moist lakeside air as you ride south to your home for the evening, the distinctive eco-friendly City Flats Hotel in the Dutch-inspired city of Holland. This fantastic small town has a charming and award-winning downtown which you will have the opportunity to explore as you decide where you would like to fuel up for tomorrow's big ride.

Today's Ride:

Milwaukee, WI to Holland, MI
Approximately 40 miles with 705 feet of climbing

Today's Date:

September 19

Hotel:

City Flats Hotel Holland

Included Meals:

Breakfast | Lunch

Today you will zigzag your way southeast through the open countryside and farms of lower Michigan. Enjoy another fabulous picnic prepared by your guides at a perfectly situated park in Prairieville Township. If you are a car fanatic, be sure to stop at the Gilmore Automobile Museum, which you'll pass just after lunch. Your path will continue to zigzag its way past the outskirts of Battle Creek to the town of Marshall – home to some interesting places such as the Honolulu House, The American Museum of Magic, and our favorite, the Dark Horse Brewery.

Today's Ride:

Holland, MI to Marshall, MI
Approximately 91 miles with 2,473 feet of climbing

Today's Date:

September 20

Hotel:

Holiday Inn Express

Included Meals:

Breakfast | Lunch | Dinner

Gear up for a big ride today! Today’s ride will have you pedaling in a variety of settings from quiet farm fields to the suburban community of Rossford. After meandering through the small towns and lakes of southeastern Michigan, drop into Ohio, the tenth state of your journey. We break for lunch at a favorite local spot, Randy’s BBQ. After some mouth-watering hickory smoked barbecue, we pedal ten miles on the quiet, smooth blacktop of the Falling Waters Trail before reaching our home for tonight in the outskirts of Toledo.

Today's Ride:

Marshall, MI to Rossford, OH
Approximately 120 miles with 1,949 feet of climbing

Today's Date:

September 21

Hotel:

Hampton Inn Toledo-Perrysburg

Included Meals:

Breakfast | Lunch | Dinner

Today is the last “flat” day of riding on this trip! The majority of our ride is on the North Coast Inland Trail bike path, which was built on the abandoned Toledo, Norwalk and Cleveland Railroad. The railroad was constructed in 1851 serving as a vital link between Chicago and Cleveland and leading to the founding of many of the small towns you will pass through on today's ride. We will end our ride in the college town of Oberlin, where we’ll enjoy a night at The Hotel at Oberlin, a modern, yet traditional LEED Platinum hotel, making it one of the most environmentally sustainable hotel projects in the U.S. Dinner will be served at 1833, the hotel’s restaurant, with its socially conscious menus using ingredients from local farmers. After dinner, it’s a short walk to the local ice cream shop. We recommend enjoying your second dessert (you’ve earned it) as you stroll through the historic Tappan Square.

Today's Ride:

Rossford, OH to Oberlin, OH
Approximately 86 miles with 1,188 feet of climbing

Today's Date:

September 22

Hotel:

The Hotel at Oberlin

Included Meals:

Breakfast | Lunch | Dinner

The hills gradually pick up today as we pass through acres of farmland before dropping down to the Cuyahoga River and riding through Cuyahoga Valley National Park. From here, it won't be long before you'll be sharing the road with the horse-drawn buggies of the local Amish population. Today's ride ends in Geauga County, home to the world's fourth largest Amish community. We'll soak it all in as we settle in for the night at a unique bed and breakfast filled with Amish influences.

Today's Ride:

Oberlin, OH to Burton, OH
Approximately 81 miles with 3,347 feet of climbing

Today's Date:

September 23

Hotel:

Red Maple Inn

Included Meals:

Breakfast | Lunch | Dinner

Find yourself in rolling terrain today as you cruise through northeastern Ohio on your way to your eleventh state of Pennsylvania. This relatively short ride will allow you to rest up for the string of four centuries to follow. Be sure to stop and see the carp at the spillway at Pymatuning Reservoir. The fish are so plentiful, that ducks can walk on their backs. We kid you not.

Today's Ride:

Burton, OH to Meadville, PA
Approximately 59 miles with 1,951 feet of climbing

Today's Date:

September 24

Hotel:

Holiday Inn Express Meadville

Included Meals:

Breakfast | Lunch | Dinner

Today's ride continues through an area noted for its Amish communities. Amish people are known for valuing simplicity, emphasizing family and community, and for their separation from the modern world including amenities such as electricity (although some groups have become more liberal in their views and practices). The riding continues to be challenging through these rolling hills but the lush, serene country is sure to boost your mood and your spirits as you near the east coast. Today climaxes with a ride along the Allegheny River, past the impressive Kinzua Dam and through the beautiful foliage of the Allegheny National Forest.

Today's Ride:

Meadville, PA to Bradford, PA
Approximately 101 miles with 5,453 feet of climbing

Today's Date:

September 25

Hotel:

Holiday Inn Express Bradford

Included Meals:

Breakfast | Lunch | Dinner

Before you leave today make sure you pick up a commemorative Zippo lighter straight from the town where it all started. Then you'll head out to cross the border into number twelve: New York! Settle in for a scenic but challenging ride full of ups and downs as you head to Corning today, which many will know for its manufacture of glass and ceramic products by Corning Incorporated, as well as being recognized as a top twenty-five small-city art destination. Tonight, you'll enjoy a relaxing dinner with your cross-country comrades and toast to the past 38 days!

Today's Ride:

Bradford, PA to Corning, NY
Approximately 101 miles with 4,634 feet of climbing

Today's Date:

September 26

Hotel:

Radisson Hotel Corning

Included Meals:

Breakfast | Lunch | Social Hour | Dinner

Awake to your final rest day in the Crystal City. Linger over that cup of coffee as you reflect on how far you've come. Only a tad over 500 miles remain on this epic journey of yours! But today is yours to relax. Stroll along the banks of the Chemung River or visit the Corning Museum of Glass or the Rockwell Museum of Western Art. Take some time to explore the historic downtown with its many galleries, shops, and restaurants. You can also use this day to get your last stash of clean clothes ready, check your emails, and bring friends and family back home up to speed on your adventures so far! Only a little more than 500 miles and 28,000 feet of climbing left to conquer.

Today's Date:

September 27

Hotel:

Radisson Hotel Corning

Included Meals:

Breakfast

Today you'll ride north through New York's famous Finger Lakes Region where you'll catch glimpses of Seneca Lake and the rugged cliffs above. Watkins Glen at the south end of the lake is not only known for its picturesque views and water activities, but also for its street car racing. Tonight, you'll stay at cozy Brewster Inn in the quaint town of Cazenovia. This is the perfect place to reminisce about the highlights and achievements of your journey and plan for the excitement and triumphs of the days ahead.

Today's Ride:

Corning, NY to Cazenovia, NY
Approximately 100 miles with 5,510 feet of climbing

Today's Date:

September 28

Hotel:

The Brewster Inn or Brae Loch Inn

Included Meals:

Breakfast | Lunch | Dinner

This morning shortly after leaving Cazenovia, you'll find yourself on a stunning descent alongside a babbling brook and waterfall. Our route also intersects with the Erie Canalway Trail, a 365-mile bike trail that follows active and historic sections of the Erie Canal. Later, you'll pedal your way into Adirondack Park. The distinctions between the Adirondacks and Rocky Mountains are easy to see, with the contrasting dome-shaped summits of the Adirondacks covered in spruce, pine, and broad-leafed trees and the highest elevation reaching just above 5,000 feet. The riding here is really rewarding as you gradually pedal up the climbs and enjoy the accompanying views of the forest and tranquil lakes before descending to our home for tonight on the shore of Piseco Lake.

Today's Date:

September 29

Hotel:

The Irondequoit Inn or Oxbow Lake Motel

Included Meals:

Breakfast | Lunch | Dinner

Enjoy a fabulous ride today as you work your way out of the Adirondacks and head to the historic and strategic outpost town of Ticonderoga. This is the home of Fort Ticonderoga and the point between Lake George and Lake Champlain. Battles were fought at this fort in both the French and Indian War and the Revolutionary War. And for movie fans, this fort was used to film many scenes in "The Last of The Mohicans." The scenery of this area will not disappoint.

Today's Ride:

Piseco, NY to Ticonderoga, NY
Approximately 84 miles with 3,968 feet of climbing

Today's Date:

September 30

Hotel:

Best Western Plus Ticonderoga

Included Meals:

Breakfast | Lunch | Dinner

Today begins with a quick float across Lake Champlain on the Ticonderoga Ferry. Enjoy spectacular lake views as you say goodbye to New York and enter colorful Vermont, your thirteenth state. From here it's on to the flourishing Green Mountains and a tough day in the saddle. The climbs here are spunky, but rest assured our chosen one, Brandon Gap, is a relatively gentle climb compared to the other passes through these mountains–and it has a rewarding open descent. Save some energy because you still have more hills to conquer in the second half of this ride before you can kick your feet up at the historic Lake Morey Resort. This resort was built in the early 1900s by Samuel Morey, the inventor of the internal-combustion engine.

Today's Ride:

Ticonderoga, NY to Fairlee, VT
Approximately 94 miles with 6,528 feet of climbing

Today's Date:

October 1

Hotel:

Lake Morey Resort

Included Meals:

Breakfast | Lunch | Dinner

Today you can almost taste the end of your long and rewarding journey, but it's not over quite yet! Your ride begins by crossing the Connecticut River and entering state number fourteen: New Hampshire. Then, one more stunning scenic byway awaits as you traverse the White Mountains. Today's ride may “only” be 83 miles, but there are three tough climbs to conquer before you enjoy a triumphant lunch at the top of Kancamagus Pass (affectionately known by the locals as "The Kanc"). You will see why many people come here to witness some of the best fall foliage in the country. And better yet, after lunch, you get to enjoy a 25-mile descent. You have definitely earned it! If you have a sweet tooth don't miss the delicious treats waiting on the other side of the mountains at the White Mountain Cupcakery in North Conway.

Today's Ride:

Fairlee, VT to North Conway, NH
Approximately 83 miles with 6,327 feet of climbing

Today's Date:

October 2

Hotel:

Green Granite Inn

Included Meals:

Breakfast | Lunch | Dinner

At last, it’s time for the final celebratory ride of this amazing journey. Today is your victory lap... your cross-country Champs Élysées! After 10 quick miles, you’ll enter Maine, your fifteenth and final state. As you approach the Atlantic, the familiarity of coastal breezes and the smell of salt water in the air will transport you back to the day when you set out from Astoria to pedal your way across the great United States. Your ride will come to an end on the sandy shore of Crescent Beach State Park on Cape Elizabeth, which is situated just south of Portland. The celebration begins here and will continue for the rest of the day! After a champagne toast on the beach, we’ll enjoy lunch at a nearby café and then make our way to the Press Hotel in downtown Portland. The Press Hotel has consistently been rated the best hotel in the city since it opened in 2015, and you’ll see why the moment you enter the lobby. Enjoy your luxury accommodations and our final gourmet feast this evening – you’ve certainly earned it!

Today's Ride:

North Conway, NH to Portland, ME
Approximately 76 miles with 2,938 feet of climbing

Today's Date:

October 3

Hotel:

Press Hotel

Included Meals:

Breakfast | Lunch | Social Hour | Dinner

A celebratory farewell breakfast and a leisurely morning in Portland offers you the opportunity to revisit the triumphs and challenges of the past 46 days. This ride-of-a-lifetime has come to a close, but the friendships and memories produced by this epic journey have just begun. We recommend flying out of Portland International Jetport (PWM) to depart to the destination of your choice.

Today's Date:

October 4

Included Meals:

Breakfast

Hotels

hotel image

Cannery Pier Hotel

Astoria, Oregon

Built on the site of the former Union Fish Cannery, the Cannery Pier Hotel is located 600 feet into the Columbia River. From this unique and enviable position, it offers guests unparalleled views of a real working river, as well as views out to Cape Disappointment Lighthouse and the impressive Astoria–Megler Bridge. Each room has a private balcony and a fireplace, hardwood floors, and luxurious amenities. Take advantage of the authentic Finnish sauna before embarking upon the first ride of your long journey.
hotel image

DoubleTree Hotel Missoula - Edgewater

Missoula, Montana

The Doubletree Edgewater is located in the heart of the college town of Missoula, on the banks of the Clark Fork River. The campus of the University of Montana is only three blocks away and the restaurants and main attractions of downtown are within walking distance. You may decide to take advantage of the world-class fly fishing right out the door, or maybe just kick back and take in the stunning views of Mount Sentinel and watch the river flow past.
hotel image

Hotel Alex Johnson

Rapid City, South Dakota

Enjoy the authentic Native American decor at this historic hotel in the heart of downtown Rapid City. The guest rooms have been recently renovated, although we understand some may still be haunted. Spend your rest day visiting Mt Rushmore, Crazy Horse or the wild west town of Deadwood.
hotel image

The Madison Concourse Hotel

Madison, Wisconsin

The Madison Concourse Hotel is a gem of a hotel with modern decor, comfortable furnishings and a wonderful fitness center with a pool, whirlpool and sauna. Steps from the center of Madison, it is the perfect location for a day of exploring. Tour the Capitol or Museum of Contemporary Art or take a stroll down State Street. Be sure to kick your feet up with a beer or a scoop of Babcock ice cream at the Memorial Union Terrace overlooking Lake Mendota.
hotel image

Radisson Hotel

Corning, New York

The Radisson Corning offers the perfect blend of comfort and convenience. It is located in the city's downtown Gaffer District, just steps from the historic Market Street filled with restaurants, boutiques and glass studios as well as the famous Corning Museum of Glass. The hotel features a full service on-site spa.
hotel image

Press Hotel

Portland, Maine

The Press Hotel is a boutique luxury hotel in Portland’s famed Old Port District. It’s part of the Autograph Collection by Marriott, which features unique and imaginative properties selected for their quality, bold originality, rich character and uncommon details. Enjoy the array of artwork throughout the hotel and your beautifully appointed guest room with its oversized windows, marble-tiled bathrooms, luxury linens, vintage desks and conveniently located USB ports.

What's Included

For us, the details matter most

Every moment of a Trek Travel bike trip has more than you could have ever dreamed. More romance. More scenery. More choice. It's the little additions to every Trek Travel cycling vacation that make it truly special. And that's how we help you create more memories.

bike

Trek Domane SL 7 Disc

It isn’t the cycling vacation of a lifetime unless you have the industry’s best bike to match. Starting in 2019, we’re upgrading our fleet to feature the award-winning Domane SL 7 with Shimano Ultegra Disc brakes. Because when you combine the lightweight stability and comfort of the Domane with the superior safety and stopping power of disc brakes, you get a match made in cycling heaven. And the best part? It’s included in the trip price. Ride confidently, comfortably and longer in the most beautiful destinations around the world with the new Domane SL 7. Learn More

WHAT'S INCLUDED

  • 46 nights of accommodation at handpicked hotels
  • Two experienced guides to provide local knowledge, support, and camaraderie
  • Daily route support with both guides and our support van
  • Daily breakfast, 40 lunches and 36 dinners
  • 6 social hours of drinks and hors d'oeuvres
  • Ride a Trek Domane SL 7
  • Snacks and drinks for each day's ride
  • Custom Cross Country Trek Travel Bontrager cycling jersey and socks to keep
  • Trek Travel water bottles to keep
  • Each bike is equipped with a Garmin Edge 1030 GPS computer, flat pack, front and rear Bontrager Flare R lights, a Bontrager saddle and pedals (Shimano clipless road pedals, Shimano clipless mountain pedals, caged or flat pedals)
  • All gratuities for drivers, local experts and hospitality staff
  • All luggage transfers and transportation during your trip
  • A personalized photobook of your trip
  • Entrance fees for all activities, private tours and events

GEAR

  • Trek Domane SL 7 carbon road bike with Shimano Di2 electronic shifting
  • Custom Cross Country Trek Travel Bontrager cycling jersey and socks to keep
  • Trek Travel water bottles to keep
  • Shimano clipless road pedals, Shimano clipless mountain pedals, caged or flat pedals
  • Bontrager helmet and saddle
  • Bontrager front and rear Flare R lights and a flat pack
  • Garmin Edge 1030 GPS computer
  • Upgrade your bike to include carbon wheels (+$200)
  • Coupon valued up to $500 off a new Trek Bicycle. Your coupon will be delivered via email prior to your trip.
  • You may bring your own pedals and saddle on the trip. Your guides will install your gear on the first day during your bike fit.

WHAT'S NOT INCLUDED

Gratuities for your Trek Travel guides are not included in your trip price. We recommend tipping 7.5-10% of your trip price for the guide team. Local currency is preferred and unless you want to tip separately, guides will divide tips amongst themselves. Please tip your guides at your discretion, based on their level of professionalism, guest care and service.
  • Airfare and transportation to and from the trip pick-up/drop-off locations
  • Lodging before and after the trip
  • Personal items purchased during the trip
  • Optional activities not scheduled by Trek Travel
  • On select trips some meals are not included. On these trips, Trek Travel invites you to explore the local cuisine at your leisure.

More Information

Rider Level: 4 - Avid?

AVERAGE DAILY MILEAGE:
73 miles
TOTAL MILES:
3710 miles
AVERAGE DAILY ELEVATION:
3,281 feet
TOTAL ELEVATION:
154,228 feet
TERRAIN: HILLY
The terrain is extremely varied, including rolling roads along rivers, long gradual climbs and descents across the plains, as well as long and steep climbing and descending in the Rockies and the Appalachians. Roads are primarily two-lane secondary highways with good shoulders, but include some short stretches of primary highways with wide shoulders, and smaller local roads and surface streets with little or no shoulder. Some road surfaces may be rough. Cross Country USA: Portland to Portland is best suited for our Type 4 Riders, due to the extreme physical demands of the trip.
NON-RIDING ACTIVITIES:
This destination is best suited to guests who want to cycle every day. Because of the terrain and/or remoteness of the hotels and riding routes, there are few, if any, non-riding options available. If a non-rider wants to accompany a rider guest on this trip, they would need to spend many hours in the van and/or at the hotels on the trip. Due to this, we strongly discourage non-riders from this destination. As an alternative, call a Trek Travel Trip Consultant at 866.464.8735 for trip suggestions where more non-rider activities are available, such as:
  • Costa Brava
  • California Coast
  • Crater Lake and the Oregon Cascades

See itinerary for specific daily ride distances and elevation options. On all of our vacations, Trek Travel strives to find quiet, paved secondary roads or bike paths to experience a region; busy roads are avoided as much as possible. Our itineraries are an approximation of our trips. Trek Travel strives to offer every guest a vacation of a lifetime on every trip. At times routes, hotels, activities, etc. listed here may change at the discretion of the trip designer or guides to improve the trip experience.

Averages and totals are calculated from our "Avid Ride" options.

Travel Details

How to Get There

FLY INTO:
Portland International Airport (PDX)
MEETING TIME:
9:00 AM
MEETING LOCATION:
Hotel Lucia, Portland, Oregon

Say Farewell

FLY OUT OF:
Portland International Jetport (PWM)
DEPARTING TIME:
10:00 AM
DEPARTING LOCATION:
Press Hotel, Portland, Maine

Arriving

We suggest that you arrive at least one day prior to the trip start, which will enable you to adjust to the time zone and minimize the risk of missing the trip start due to flight-related delays.

We recommend that you fly into Portland International Airport (PDX), which is approximately 12 miles from downtown Portland. All major airlines serve this airport and there are numerous options for getting downtown. The least expensive option is the MAX Light Rail Service. The Red Line picks passengers up in the baggage claim area and costs about $2.50 per person for a ride downtown, which takes about 40 minutes. If you are staying at the pickup hotel, Hotel Lucia, get off at the Pioneer Courthouse Square stop and the hotel is a three block walk up Broadway. Alternatively, contact Blue Star Transportation (www.bluestarbus.com, 503 249 1837) to book a seat on a regularly scheduled shuttle from PDX to downtown for $14 per person. This will take between 40 minutes to an hour, depending upon traffic. Or, you can simply hail a taxi outside baggage claim, which will cost approximately $35 plus gratuity and should take about 30 minutes, depending on traffic.

Your Trek Travel guides will meet you at the Hotel Lucia (400 SW Broadway, Portland, Oregon) at 9:00 AM on the first day of the trip. You will then shuttle approximately 2 hours to the Cannery Pier Hotel in Astoria, Oregon. If you prefer to drive to the first hotel to meet the group, you may use Enterprise to rent a car at PDX and drop it off at the Enterprise office just across the street from the Cannery Pier. Please let your Trek Travel Trip Consultant know if you will be meeting the group here instead of Hotel Lucia. After a welcome lunch at the hotel, your guides will do a thorough bike fit to ensure your comfort and answer any questions you have about your trip. Please come prepared with pedals, shoes, saddle, bike fit measurements, and anything else you would like affixed to your bike. Have these items and your riding clothes packed in a small, easily accessible bag. The hotel can store your larger pieces of luggage until check-in time.

If you will be late for the pick-up or are going to miss it altogether, please inform your guides. You will receive an email a week before the trip start with their names and contact details. If you cannot reach them, please call our first hotel, Cannery Pier Hotel (503 325 4996), and leave a message with your expected arrival time and contact details. Your guides will be aware that you are late and will be in contact with the hotel. If you need to book transportation on your own from downtown Portland to Astoria we suggest contacting Northern Lights Towncar (www.northernlightstowncar.com, 503 760 2478). You can arrange a private shuttle for up to 3 people for around $210.

View our pre hotel recommendations

Leaving

You will say farewell to your guides at 10:00 AM at the Press Hotel, Portland, Maine. We recommend that you fly out of the Portland International Jetport (PWM), which is located about 6 miles from the Press Hotel. If you wish to take advantage of the hotel’s free airport shuttle, please inform the front desk when you check-in so they can schedule it for you. Alternatively, a taxi will cost approximately $15.

View our post hotel recommendations

Planning For Your Trip

Packing and Weather

The weather across the country will be extremely varied. You can expect all conditions including rain, snow, fog, wind, sun, heat, and cold, in both humid and arid climates. Extreme weather conditions may exist in certain parts of the country. Your guides will monitor the safety of riding in such conditions and will delay or cancel rides if they deem the conditions to be too dangerous. Bring adequate layers and riding gear for riding in any and all conditions. Packing List

Before and After Your Trip

before

Before: Portland, Oregon

P:We recommend spending a few days in the vibrant, bustling city of Portland, Oregon. An excellent public transit system makes it easy to get around the City of Roses (so named because its climate is very conducive to growing rose bushes). Portlanders are widely known for their enthusiasm for local food, microbrews, coffee, art, and bikes. The Willamette River flows through downtown and constitutes the boundary between east and west sections; Burnside Street divides north and south; and the North section is defined by the river to the west and Williams Avenue to the east. Locals use these sections to give directions, so it's good to be familiar with the general idea! Farm to table restaurants, food carts, bike shops, fun and funky architecture, book stores (don't miss Powell's City of Books in the heart of downtown!), parks, and museums are abundant in this quintessential city of the Pacific Northwest. We recommend the following accommodations for your pre-trip hotel.

after

After: Portland, Maine

The city of Portland, Maine (for which Portland, Oregon was named) has a relaxed, small-town feel that makes it an ideal place to unwind after your ride across the country. Take a few extra days to explore the cobbled Old Port District, check out the working waterfront and Portland Museum of Art in the arts district, and visit some of the many historical sights in town. Take a trolley tour or a lighthouse tour, or visit the Wadsworth-Longfellow House, childhood home of the American poet Henry Wadsworth Longfellow. According to locals, Portland has more restaurants and bars per capita than any other city in the country outside of San Fransisco. Many of the more popular restaurants are chef-owned and highly renowned. Kick back and take in the sights and smells of the Atlantic as you relax at the conclusion of your epic trip. We recommend the following accommodations for your post-trip hotel.

Customer Reviews

Why Trek Travel

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the all-new, ultra smooth Trek Domane SL 7, to the new Trek Electric-Assist XM700+ and the comfortable Trek 7.6 FX Hybrid, to our numerous upgrade options, you deserve the best ride on your vacation.

Our Guides

Our guides are trained to make your trip magical. They aren't just experts in riding; they're trained in delivering uncompromising service in ways you won't believe. We know that it's the unexpected surprises that make a trip magical. That's why our guides pride themselves on anticipating your needs before you ask.

Your Day. You Decide.

Our vacations are built to deliver the ultimate in flexibility, from extreme relaxers to hard-core roadies. You pick your mileage, itinerary and experiences. We take care of the rest.

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