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New England's Champlain Valley and Green Mountains: Middlebury to Stowe

There's no better place to celebrate the brilliance of summer or the beauty of changing seasons than Vermont’s picturesque Green Mountains. Enjoy unforgettable rides through dense forests, along winding rivers, and past hillside farms. Explore the charm of quaint town squares and sample regional specialties from golden maple syrup to smooth Vermont cheddar and rich, velvety ice cream. Ride across the historic covered Gold Brook Bridge and through the pristine Green Mountain National Forest. Vermont offers a range of cycling, hiking, and sightseeing options for any skill level so, whatever your interest, let Trek Travel bring your picture-perfect bicycling vacation to life. See Our Vermont Brewery Edition» See Our Vermont Family Edition»
$2799 Per Person
6 Days & 5 Nights
Rider Type: ?
3 / 2 - Active / Recreational Non-riders Welcome
Hotel Style: ?
Bike Included:
Trek Domane SL 7 More options available
From $2799 per person View All Details
Trip Wows
Ride quiet winding roads surrounded by the vibrant forests of the Green Mountains
Explore the historic villages of Middlebury and Stowe, famous for skiing and filled with wonderful galleries, shops and restaurants
Sample local craft beer at Otter Creek Brewery in Middlebury after riding through the Champlain Valley
Hike to Stowe Pinnacle for great views of the surrounding countryside and Mount Mansfield, Vermont's highest peak
Get to know the locals and taste some maple syrup in a small, family-owned sugarhouse
Watch the Experience
This bike tour was one of the best I've enjoyed.   The timing of autumn, the beauty of the countryside, the inns, the fellow cyclists, the tour guides all perfectly meshed to create an unforgettable trip

Dates & Prices

The earlier you book, the greater the rewards

We reward our guests with lower pricing and more dates to choose from the earlier you book. Rest assured, once you book, your price and date are guaranteed.
to run
Sold Out/

Single Occupancy from: +$750
Jun 17  – Jun  22
Guaranteed Limited Availability
$2799 / Person, Double Occupancy / Plus 7% Vermont state & local sales tax / Brewery Edition Book this date
Jun 24  – Jun  29
Guaranteed Limited Availability
$2799 / Person, Double Occupancy / Plus 7% Vermont state & local sales tax / Brewery Edition Book this date
Jul 1  – Jul  6
Guaranteed Limited Availability
$2799 / Person, Double Occupancy / Plus 7% Vermont state & local sales tax / Brewery Edition Book this date
Jul 8  – Jul  13
Guaranteed Limited Availability
$2799 / Person, Double Occupancy / Plus 7% Vermont state & local sales tax / Brewery Edition Book this date
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. Private pricing is not available on Ride Camp, Race, Special Edition or Cross Country style trips.
After a scenic one-hour private shuttle, you’ll arrive in Middlebury, home to one of the oldest liberal arts colleges in the country. A picnic lunch prepared by your Trek Travel guides awaits you in this beautiful town, which is located between the foothills of the Green Mountains and Lake Champlain. After a short round of introductions, your guides will discuss the rules of bike safety and specific cycling tips for riding in Vermont before familiarizing you with your Trek bicycle and ensuring a comfortable fit. The rest of the day is yours to explore! Settle into the inn or take your first ride through the rolling farmland around Middlebury, past the University of Vermont Morgan Horse Farm and views of the Adirondacks. This evening kicks off with a social hour at Morgan's Tavern at the inn. Your guides will fill you in on the details of the week over drinks and afterwards, get to know your fellow travelers during a fun dinner at The Lobby. This restaurant is located on Bakery Lane in downtown Middlebury and specializes in unique, locally-sourced dishes—try the local filet mignon burger!
Today's Ride:

Weybridge Loop
Approximately 24 miles with 1,600 feet of climbing


Middlebury Inn

Included Meals:

Lunch | Social Hour | Dinner

This morning we head south on a ride out of Middlebury through Farmingdale and Salisbury. Enjoy views of the mountains to the east and Lake Champlain to the west before arriving in the historic town of Brandon to enjoy lunch at the cafe of your choice. Continue riding back to Middlebury, along the shores of beautiful Lake Dunmore, or alternatively choose to shuttle back to relax at the inn or maybe take in the distinctive New England culture in the Frog Hollow art galleries and marble works. Browsing through one of the many antique shops or bookstores in the area is also a great way to spend an afternoon. If you're up for a challenge, ride up to Middlebury Gap—a tough but rewarding climb past the Middlebury College Snow Bowl and the Bread Loaf Campus. This afternoon you'll also have the option to join the group for a local craft beer sampling at the Otter Creek Brewing Company. Tonight you are on your own to explore the many dining options in town.
Today's Ride:

Brandon Loop
Approximately 43 miles with 2,100 feet of climbing

Short Option:

Middlebury to Brandon
Approximately 20 miles with 1,000 feet of climbing

Avid Option:

Brandon Loop with Middlebury Gap
Approximately 59 miles with 3,700 feet of climbing


Middlebury Inn

Included Meals:

Breakfast | Social Hour

Say goodbye to Middlebury this morning as you begin the day with a one-hour shuttle to the hamlet of Warren, which is located on the banks of the Mad River. Stop into the Warren Store and browse this classic landmark before hopping on your bike and heading north through the Mad River Valley, crossing the Pine Brook Covered Bridge on the way to Waterbury. Here you can browse local boutiques and gift shops like Green Mountain Coffee Roasters or the Craft Beer Cellar before convening at local bistro Cork for a delicious lunch. Your next stop is the Ben & Jerry’s Ice Cream Factory, where the company motto decrees “Life is short; eat dessert first.” Choose from many interesting flavors for your afternoon treat! Afterward, continue to Stowe along quiet roads with sweeping views. If you're interested in more miles, you may tackle the steep climb up and over Smuggler's Notch to check out the narrow mountain pass between Mount Mansfield and Spruce Peak. Or you may take your time to explore the town's interesting shops, get a massage and relax at one of the spas, or maybe just enjoy a stroll along the winding Recreation Path. Tonight you will gather for dinner at The Whip at the Green Mountain Inn.
Today's Ride:

Warren to Stowe
Approximately 38 miles with 2,500 feet of climbing

Short Option:

Warren to Waterbury
Approximately 27 miles with 1,400 feet of climbing

Avid Option:

Warren to Stowe with Smuggler's Notch
Approximately 61 miles with 4,800 feet of climbing


Green Mountain Inn

Included Meals:

Breakfast | Lunch | Dinner

Today you will continue exploring Vermont by heading north on Route 100 for a spectacular ride which passes through lush pastures and farmland. Pedal into the town of Johnson, a charming village nestled in the mountains, and take some time to explore its unique shops and boutiques, including the Johnson Woolen Mills factory with its iconic selection of signature woolen goods. This afternoon you’ll pedal through a scenic landscape decorated with white church steeples, bright red barns and fields of lazily grazing cows. Choose your own lunch stop in either Johnson or Jeffersonville, then decide whether you’ll shuttle in the van or hunker down for the climb up the west side of Mount Mansfield to Smuggler’s Notch and the rewarding descent down to the West Branch River and Stowe. This evening, you'll head to a local sugarhouse for a private tour and maple syrup tasting—you’ll come away with a newfound appreciation for the art and science of “sugaring." Tonight you’re on your own for dinner in Stowe; your guides, however, will have lots of great recommendations!
Today's Ride:

Stowe to Jeffersonville
Approximately 35 miles with 1,400 feet of climbing

Short Option:

Stowe to Johnson
Approximately 24 miles with 1,300 feet of climbing

Avid Option:

Smuggler’s Notch Loop
Approximately 53 miles with 3,200 feet of climbing


Green Mountain Inn

Included Meals:


Start with a hearty breakfast to prepare you for the day's activities. Your morning ride will take you past the site of the original settlement of Stowe, which dates to the late 1700s. Enjoy a fantastic loop through lush Vermont farmland that passes through the village of Morrisville. Then tackle the beautiful rolling hills on Stagecoach Road before returning to Stowe for a lunch of your choosing at one of the local cafes. This afternoon you'll have a chance to hike the Stowe Pinnacle Trail. A 3-mile out and back hike just minutes from downtown Stowe, this moderate trail winds its way to a beautiful rock vista overlooking the spectacular Green Mountain Range. This evening you and your traveling companions will gather for drinks at the Inn before heading out to Michael’s on the Hill for a final delicious dinner. Michael and Laura Kloeti, the chef and owners of Michael’s, have been awarded Vermont Restauranteurs of the Year and the restaurant has received The Wine Spectator Award of Excellence and Santé Magazine’s Sustainable Restaurant Award. Their firm commitment to local, organic products and the slow food movement is evident in their menu, which makes for the perfect plate over which to toast new friends, great adventures and your week experiencing quintessential New England culture.
Today's Ride:

Stagecoach Loop with Garfield Road
Approximately 30 miles with 2,000 feet of climbing

Short Option:

Stagecoach Loop Direct
Approximately 20 miles with 1,200 feet of climbing

Avid Option:

Stagecoach Loop with Weeks Hill
Approximately 33 miles with 2,500 feet of climbing


Green Mountain Inn

Included Meals:

Breakfast | Social Hour | Dinner

This morning’s loop is the perfect final ride and farewell to Vermont as you cycle the quiet roads surrounding Stowe, past the Gold Brook Bridge—one of the oldest and most storied (and allegedly haunted) covered bridges in Vermont. Soak in the New England countryside one last time and ride up to the Trapp Family Lodge, a reconstructed version of the grand lodge once home to the family whose story inspired “The Sound of Music.” If you’d rather skip the ride, sleep in, have a leisurely breakfast and then enjoy a final stroll through the streets of Stowe to savor a few last moments of your week and maybe pick up some souvenirs and gifts. A private Trek Travel shuttle will depart from the Inn at 11:00 AM to take you to Burlington.
Today's Ride:

Von Trapp Loop
Approximately 14 miles with 1,200 feet of climbing

Included Meals:



hotel image

Middlebury Inn

Middlebury, Vermont

The Middlebury Inn has been welcoming visitors since 1827 and exudes a wonderful blend of historic charm and modern comfort. An official "Green Hotel in the Green Mountain State" and a Historic Hotel of America, the Middlebury Inn takes special care to provide an experience that is true both to its New England roots and its commitment to the community. You will stay in a Luxury room in the historic Main Inn or the Porter Mansion during your visit. The Inn features a day spa and is located within walking distance of the shops, restaurants, and attractions of downtown Middlebury.
hotel image

Green Mountain Inn

Stowe, Vermont

Situated in the center of the village of Stowe, the Green Mountain Inn has a rich and interesting history. The property, listed on the National Register of Historic Places, has been welcoming guests (including former U.S. Presidents) since the mid-1800s, when it served as a stagecoach stop, and has operated under its current name for 122 years. Over the generations, the Inn has been transformed into the beautiful property that it is today through upgrades designed to retain and blend the Inn’s historic charm and traditional feel with the very best amenities and comfortable accommodations.

Travel Details

How to Get There

Burlington International Airport (BTV)
11:00 AM
Hilton Burlington, Burlington, Vermont

Say Farewell

Burlington International Airport (BTV)
2:00 PM
Hilton Burlington or Burlington International Airport, Burlington, Vermont


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 Burlington International Airport (BTV). From the airport, you can call or hail a taxi to take you downtown. It is approximately 4 miles from the airport to the meeting day hotel in downtown Burlington and a taxi ride should take about 10-15 minutes and cost $20-$25.

Your Trek Travel guides will meet you at the Hilton Burlington (60 Battery Street, Burlington VT 05401) at 11:00 AM on the first day of the trip. You and your traveling companions will take a private shuttle to Middlebury, just over an hour from Burlington, for a picnic lunch before beginning the first ride of the week. Please have your first day’s riding gear handy and separate from your other luggage to facilitate the bike fitting and ride.

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, Middlebury Inn (802-388-4961), and leave a message with your expected arrival time and contact details. A taxi from Burlington to the first night’s hotel is available from Green Cab for approximately $95 plus gratuity. Call 802-864-2424 to make arrangements.

View our pre hotel recommendations


You will say farewell to your guides at 12:00 PM at the Hilton Burlington or Burlington International Airport (BTV). Please do not schedule a flight out of Burlington International Airport before 2:00 PM on the last day of the trip to allow plenty of time for any unforeseen delays.

View our post hotel recommendations

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.


Trek Domane SL 7

Trek’s latest innovation has led to the best bike on the road—a light weight, stable and technologically advanced machine to make even the hardest roads seem easy. Ride confidently, comfortably and longer in the most beautiful destinations around the world. Upgrade your bike with carbon wheels for only $200. Learn More


Trek Electric-Assist XM700+

It’s lightweight and equipped with an adjustable pedal-assist motor that helps riders of all skill levels stay together, play together and make some great memories together. Included at no additional cost, these bikes will be available on a first-come, first-served basis, so reserve yours when you book today. Learn More

Trek 7.6 FX Hybrid

Trek 7.6 FX Hybrid
is also available on this trip


  • 5 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, 2 lunches and 3 dinners
  • Social hour of drinks and hors d’oeuvres on your first and last night of the trip
  • Ride a Trek Domane SL 7, Trek’s newest Electric-Assist, or a Trek 7.6 FX Hybrid
  • Three daily route options
  • Snacks and drinks for each day’s ride
  • Trek Travel Bontrager RL cycling jersey
  • 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 of your choice
  • 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


  • Trek Domane SL 7 carbon road bike with Shimano Di2 electronic shifting or Trek 7.6 FX Hybrid bike to use
  • Trek Electric Assist XM700+ also available in a limited quantity to use
  • Trek Travel Bontrager RL cycling jersey
  • Trek Travel water bottles
  • Shimano clipless road pedals, Shimano clipless mountain pedals, caged or flat pedals
  • Bontrager helmet and saddle to use
  • Bontrager front and rear Flare R lights
  • Flat pack
  • 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.


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: 2/3 - Recreational/Active?

31 miles
184 miles
1,800 feet
10,800 feet
The terrain is varied, with rides in wide valleys of rolling farmland and also more mountainous areas. All of the rides are highlighted by rewarding vistas and winding roads, thanks to the beautiful Green Mountains. Please be aware that you will encounter sections of gravel roads throughout the week. As always, if you wish to skip these sections you are welcome to shuttle in the support van. Vermont is best suited for our Type 2 and 3 Riders. Our Trek Travel guides can also easily accommodate Type 1 and 2 Riders, who seek less mileage or fewer uphills, with a boost in the van or the short route options. Those who wish to ride every mile but are concerned about their physical ability may want to try our electric bike option–you still get a workout but can climb alongside even the strongest rider. Type 3+ Riders will enjoy the extra mileage the avid route options offer.
On most Trek Travel trips, we offer non-riding options for riders who want to take the afternoon off, or travel companions who want to spend little or no time in the saddle. Some of these options may need to be scheduled before your trip–please contact one of our Trip Consultants for more information. Expenses and/or related transportation to these activities may not be included in the trip price. Some non-riding options on this trip are:
  • [Non-rider list that is already there]

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 Today’s Ride options.

Planning For Your Trip

Packing and Weather

During the month of August, expect daytime temperatures in the mid 70s and nighttime lows in the low 50s. Fall weather varies in northern Vermont, generally warmer in September and chilly by mid-October, with highs in the 50s and freezing overnight. Layers are always recommended, as you can expect cool mornings all season. Rain is also a distinct possibility in Vermont any time of year, so check the forecast in the days prior to your departure and always bring your rain gear, just in case. Packing List

Before and After Your Trip


Before & After: Burlington, Vermont

Burlington is a vibrant and beautiful college town on Lake Champlain, with a great variety of leisure and outdoor adventure activities at your fingertips. Not to be missed are the shopping and dining opportunities along Church Street, Burlington’s pedestrian mall. Rent a kayak or sailboat and set out to enjoy Lake Champlain from Burlington Harbor. Visit the Shelburne Museum, one of the finest museums in New England, highlighting the history and the culture of the region, or maybe stop by the Magic Hat Brewery and sample one of their many exceptional seasonal brews. We recommend the following accommodations for your pre and 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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