Skip to main content

Cross Country USA: Montana to South Dakota

Days 12-19: Missoula, MT -> Rapid City, SD. 1638 total miles and 42,887 ft of total elevation.

Day 12: Missoula, Montana Our first rest day was over and our clutch of riders was anxious and eager to get going. So much so that the guides released us early. On tap for the next 8 days: five days of 100+ miles plus two in the 90’s and an easier day of 73. The sound of so many cycling shoes clicking into pedals was a welcome musical note as we lit out for Helena, 117 miles and 5000 feet of elevation away. If there was a collective thought bubble it looked like this, “The rest day was fun but I’m ready to get back on the road.”

Route 12 was today’s highlight with its open ribbon byways with gigantic rock formations looming. The latter had me wishing I’d paid more attention in geology class at Princeton. The Little Blackfoot River meandered nearby and Silk’s osprey count was high.

We did a bit of climbing but the real climb came at mile 100 (Show Time at mile 100, can you believe?) when we started climbing up and over Mullan Pass. It was 4 miles of climbing though not as steep as Lolo Pass last week and with a gangbusters tailwind to boot. Our treat was to find Rae and her irrepressible smile at the top with an array of rest-stop yummies. Each guide has their own rest stop and lunching style. Rae’s whiteboards are smile-inducing.

The cross-wind whipping whirlwind 10 mile descent to the flats leading to Helena had me in a tight tuck and grinning all the way down to the flats leading into Helena. Approaching Helena we saw a cloud of windblown smoke and six helicopters choppering the skies ferrying water to a nearby wildfire.

Day 14: Bozeman, Montana This early morning found us at the Lark Hotel prepping for departure in the crisp nippy air. The sun hadn’t found us yet so our morning logistics and tasks were undertaken with quicker steps combined with short stops at the outdoor fire pit to warm hands and backsides. We were riding to breakfast at the Feed Cafe this morning and then launching into the day from there.

Blake had told us we would quickly become a well organized beehive and he was right. By now we were all on the dot each morning with no wasted steps or motion. Our tasks: donning cycling kit, putting everything back in bags that had been taken out the night before, figuring out what layers were right for the cold start and the later intense sun, getting bikes out of rooms, installing charged fore and aft bike lights, filling water bottles, making sure our labeled and packed string bags are in either the picnic or rest stop vans, snapping a pic of the white board, stuffing snacks into jersey pockets, carrying luggage to the luggage trailer, confirming room is clean, leaving a tip for the cleaning staff, triple-checking nothing has been left behind and then hopping on bikes for the mile ride to breakfast.

Bozeman to Columbus was our third century plus day and with 2700 feet of elevation it promised to be a less taxing day. We moved on out of town and in just a short while found ourselves on Bozeman Hill Road. A stunner of a serpentine road with views that would not quit. Storybook fields, meadows, and mountain views were ours along with red tail hawks soaring for good measure. One of the distinct pleasures of this adventure: a new route to be discovered every single day.

The B’s were grinning ear to ear as we swooped, exclaimed, stopped for photos and reveled in this perfection cycling in a drop dead gorgeous place. A few of us stopped to stare at the array of mountains in front of us when I happened to look behind us for an equally jaw-dropping view.

We crossed the Yellowstone River with its glacial flour milky flow. It and the surrounding expanses of fields and mountains felt timeless. I never tired of letting my eyes wander over these peaks and spaces. As the day slipped by the visuals entranced. Ian even caught a glimpse of a sleek antelope. The heat steadily ticked up and the guides added an extra rest stop at mile 100 which was more than welcome.

We pulled into the Columbus Super 8 happy to get out of the sun. Traveling in a group and in sub-groups means there are recurring themes that serve as punchlines and organizing principals. A main one? Laundry. The doing of it, the finding of machines, the sharing of soap pods, coins and intel meant it was a “takes a village” approach for smooth group execution. Before even a few days had gone by there were a subset who were sharing loads. It was also abundantly clear that Mike, with his totemic Ironman tattoo on his powerful right calf, was the Laundry Titan. Without fail he was first to find the machine(s) and relay reliable information about where, what and how. A blink of an eye too late and your bag of laundry was fifth in an orderly line on the floor awaiting its turn. This time in Columbus, Mark monitored the lone machine to then text the next person in line that their bag was up for processing.

Day 15: Lovell, Wyoming This 90 mile day distinguished itself with it’s particular stint of afternoon miles in seething heat. Looking for a sliver of shade was a fool’s errand and it took teamwork, mental fortitude and the guide’s uncanny sense of when and where to place vans for the rest stops. The remarkable landscape of MT changed as we neared the more hardscrabble border with WY. The sagebrush was more prevalent, the winds relentless.

The post-lunch 22 mile stretch was a nose to the ground push. No shade, fearsome headwinds, less treed landscape, and the road stretching out forever in front of us. It would have been a lonesome scenario were I not surrounded by the buoyancy of Sandy and Silk. Guide Blake showed up a few miles in and got in front which was fortuitous because only minutes later Sandy called out, “Jennings! Is my rear flat?” I focused in and sure enough, she had a puncture. I called ahead to Blake who wheeled around and came to help her and we pressed on knowing they’d catch back up.

Rae soon joined Silk, Sandy and me and for the next 90 minutes we traded leads and rode with heads down, legs and brains dialed in. I didn’t let my thoughts wander too much because I wanted to hold my place in our line. Preserving mental energy for moving the bike forward was paramount. If hell is other people that is not the case on this trip. Riding with others who are well-matched makes the miles slip by with even more flair. My Garmin told me later that we were facing off with 15 mph head winds. Upon arrival in Lovell my eyes were red and dried out.

Today we were completely dependent on the guides and their van stops every 13 miles after lunch and all the way to mile 90. Knowing a guide is ahead with sustenance, abundant ice and cold water plus a dose of good cheer kept us on task. We finally pulled into our oasis the Horseshoe Bend Motel. It looked humble as a barn stall and happily it was a wonderful respite complete with outdoor meals on a shady grassy parklet. We would be up and out very early in the morning for the 100 mile haul over to Sheridan. Our route? Up and over Big Horn Pass which will test mightily.

Day 16: Sheridan, Wyoming How do the guides keep track of 21 cyclists on the open road? There is no imperative that anyone ride with anyone else, there is no requirement that any particular pace or rhythm be adhered to. There’s no rule that one can’t stop at a local watering hole en route just because it’s there…just kidding.

Our ages range from 55 – 72 and the great equalizer is that we all trained steadfastly and with huge motivation for this peerless trip. Individual strengths come into play each day, every ride, mile after mile. It was athletic eye candy all day long and hugely motivating to see our group rising mightily and together to meet the daily challenges. Finding motivation in the most interesting and unexpected ways is possible with eyes and mind wide open.

The guides configure each day’s rest stops and lunch so they are synched with the overall day, suitable locations on the day’s route (is there shade?) as well as allowing for the pace differences that exist among 21 cyclists. So that the 21 of us more or less convene for lunch at the same time the guides perform a magic trick. They send us off in the morning with intervals of 15 to 30 minutes between groups. Their motto is always, “Start with your group, ride as you wish.” How is all this communicated? Both with What’s App and Ride With GPS on our phones. This way the guides can update how our day is to be organized with ease and no fuss.

By the time we had Missoula in the rear view, it was clear that Ron, Doyle, and Lynn wanted to leave as early as possible every morning so they could accomplish their day with no time worries and also be able to share lunchtime camaraderie. Blake was on board with this idea and the trio were dubbed by Doyle: the Early Birds.

For the rest of the trip, these three indomitable, upbeat, patient and persistently buoyant cyclists became the touchstone for the rest of us. Their conversations and every-mile shared experience was a model for how to combine forces and strengths. As Ron says, “It seemed like Lynn, being the strongest, would always find a way to let me lead our pace line on a downhill section!”

As the days began to pile up and the miles and elevation mounting precipitously, the Early Birds stood as testament to the rest of us, “If they are doing it, I can too.”

With the Big Horn Pass on tap for our day the 21 member string of us stretched over many many miles. It was a 100 mile, 7800 feet day. With Guides Megan and Brent on bikes, Blake, Brian and Rae had their hands full keeping the rest of us watered, fed, buoyed and on track. The task of getting up and over Big Horn Pass alternately loomed and motivated. The white board said it all: look at all those rest stops!

Our pre-dawn start lent a sense of otherworldliness to this day’s endeavor. One by one we each pedaled every single mile of this 20 mile climb. Climbing is so often a solitary endeavor with each of us bent to the task. Seeing the guides along the way either on bike or at van stops chirks us up every time. The 20 mile climb was both a challenge and a joy. I noted that akin to my experience in the Himalaya in Nepal that as the elevation goes up so does the cost of taking a sip of water. For every sip, that’s a breath not taken. Thus after the sip, breathing is on the double to catch back up.

Day 17: Gillette, Wyoming How is it to face down 109 miles after having ridden 101 miles all while tomorrow’s 111 are looming? There’s an optimism that infuses all of us on the morning starts and that bright-eyed bushy-tailed demeanor gets slowly extinguished over the course of 8+ hours out in the sun, wind and hills. No matter what ride it is and how incredibly appealing it all is, the last 10 – 15 miles are a struggle. For every single person.

I was on my way to the pool after pulling into Gillette to the Hampton Inn and I met Greg getting his luggage. He’d just finished. He looked at me with towel and board shorts and said, “Why is the last 15 miles so dang hard? Is it the heat?” He was right, it was 90 degrees as we traversed the mind numbing ugliness of the outskirts of Gillette. I said, “No matter what ride it has been the last miles are almost unbearable, aren’t they?” He smiled and said, “Just got to keep pedaling to get it done.” He was so right.

By rote I took a photo of the day’s whiteboard. I will confess to the dulling effect of all these numbers. Most mornings I snap this pic not paying one whit of attention to what is actually on the board. Sandy will come over and tell me, as she did this morning, “18. 40, 62.” Which refers to rest stop, rest stop and lunching.

I’ll say it to myself a few times, silently get astride the bike, start pedaling in the sunshine flowing like honey early morning and promptly forget the numbers.

The road out of Gillette was winding, long, quiet, with views forever and legs that were still remembering yesterday’s 7000+ climb over Big Horn Pass. Seven of us grouped together: 5 gents and 2 power women. The headwinds were relentless but not ferocious. So we took turns leading and the leader would pull for 2 miles or so before moving left, so the next rider in rotation would be up front for their chance to pull. We were seamless like that to 18, 40 and again to lunch at 62.

Today our guides showed me once again that how they do anything is how they do everything. At lunch there was not an inch of shade to be found. The guides arranged the vans so we would have a slice of shade and, like small animals at feeding time, we would each snag a small camp chair and quietly take in the needed calories. We all know the respite is short and we must soon get back on the bikes.

Not long after lunch we stopped in Spotted Horse at the biker bar and Blake lead us inside the watering hole and we emerged with ice cream bar treats. Thank you Trek Travel! Sandy and I rocked in the wooden porch chair, the bikers and their Harleys and our group with our Domanes peaceably shared this one of a kind oasis.

Maura provided the nature moment of the day when she spied the free-running herd of antelope. Check out that ungulate’s perfect middle-distance running form. Swoooon!

Day 18: Spearfish, South Dakota Our last day in WY with SD beckoning. Theme for today in this order: headwinds, crossing headwinds, crossing tailwinds, tailwinds.

Happily we scored some tailwinds on the huge uphills that has us leaving WY and heading to the Black Hills and SD. But the morning started with 25 miles on a long straight road with persistent headwinds. Sandy, Silk and I took turns pulling and taking the brunt of it. For safety’s sake (and for drafting) cyclists are usually single file. Today, the crossing winds were so strong that being single file did nothing to alleviate being slammed by the gusts. So we figured out real quick on this desolate road that the bowling pin configuration was the way to go. Silk would lead, Sandy would be to his rear and left and with her front wheel about mid-point on Silk’s bike. I was fanned out behind Sandy to her left with my front wheel halfway down the length of her bike. We had a superb rhythm going of sharing the lead and it lasted that way until the first rest stop at mile 18.

Today’s highlight was Rae’s dance in the sprinkler fountain in Sundance, WY in cycling cleats! Megan’s Sundance power lunch was four star. She always stands at the table to explain and point out what her creations are. Always delicious, always arresting.

Day 19: Rapid City, South Dakota Wish I could report that all spirits were high on this the 8th consecutive day of cycling as we departed Spearfish on Sunday morning from the somber Holiday Inn which resembled a brutalist Russian fortress on the inside.

This was the first morning I found it tough to get out of the sack being sound asleep at 5 am when the alarm went off. From colleagues who I’d not ever heard anything negative or whingey I heard, “I don’t really need today” and “I just want this ride to be over with.” It’s true that the mileage (75 miles) was do-able. It was the prospect of another 5000 foot day in the intense heat that gave pause.

My attitude: I will pedal this bike until I arrive in Rapid City. I will negotiate every hill that comes my way. I will stick with Silk and Sandy and make the day happen with full attention paid. If Ron, Doyle and Lynn can do it, I can do it, too.

As we headed directly onto the Spearfish Canyon Scenic Byway, the winding roads, the shade, the peaceful combination of huge trees, the limestone outcroppings and the sparkling rushing Spearfish Creek made it all appealing. Sandy, Silk and I started out with the idea of letting the miles unfold as they came to us. Sometimes we were near each other, other times farther apart but always mindful of re-grouping as needed and wanted. When the hills started coming I was going gangbusters. Then came a hill when I waved them on and said, “See you at the top.” My breath was getting hard and fast with the heat building.

I ate a handful of peanuts at lunch at our 45 mile mark idyllic pond-side location. It was too hot with still too much elevation to accomplish to consider a belly of food on top of the work to come. Grim determination over-ruled stuffing my pie hole.

The very last hill of the day I was far behind S and S as they started up that interminable appearing ascent. I’d been told at the last rest stop this hill was our “last uptick.” I told myself it was time to get moving and as I looked up I realized Silk was about five long white-line rumble strips ahead of me.

There were short intervals of smooth pavement between the rumble strips. Methodically I inserted a bit of rumble strip fartlek and near to when I was running out of real estate I caught up to him. My legs were stripped. I got up to the top as Silk yelled, “Yeah Jennings!!” Putting my head down, chest heaving, heart wild I told myself I’m done as I coasted for a few meters waiting for my breathing to settle down. The heat seemed a dome around my body and head. I squirted water onto my sun sleeves and poured more down the back of my neck.

The rest of the way was downhill deliciously earned. Then 4 more miles avoiding the traffic of Rapid City on a blazing hot with no shade bike trail. It was 97 wind-whipping degrees as we found our way to the beautiful Hotel Alex Johnson.

Rest day 2 is tomorrow. Done and done.

Rest Day: Rapid City, South Dakota

The state of our collective state? There were a few walking wounded in our midst. So to say the Rapid City rest day was welcome is an understatement. Even those of us who are sturdy, standing tall and coping well were relieved to know we were soon to have a day to be still. Being outdoors all day in molten heat and winds with so many many miles to travel takes the shine off each of us in just enough ways to make this, our second rest day, uber appealing. The guides are busier than a summer hive of bees all day long supporting us. On rest days we leave. them. alone.

This endeavor requires strict attention to one’s body and state of mind every day. Self-care matters deeply. Dave Edwards, our favorite Trek Travel Ride Camp guide in Greenville told us, “Everyone has a breaking point on Portland to Portland so be ready for a day that just doesn’t go your way.” So far so good.

Stay tuned for more from Lynn.

See the trip


Private

If a date is marked as Private, it is reserved for a private group.

Don’t see exactly what you are looking for or looking for a custom date?
Call our trip consultants at 866-464-8735

What is the Difference?

Ultimate Luxury:

Savor some of the most spectacular, 5-star properties in the world. Exuding luxury and elegance, these one-of-a-kind accommodations offer the chance to rejuvenate at award-winning spas, dine at Michelin-starred restaurants, and more.

Luxury:

Enjoy luxurious accommodations handpicked for a refined experience. From signature spa treatments to delicious local cuisine, you’ll be more than provided for; you’ll be pampered.

Explorer:

These handpicked hotels provide relaxation and fun in a casual and comfortable environment. Delicious cuisine and great service mix perfectly for a memorable stay.

Combined:

On select cycling vacations, you’ll stay at a mix of Explorer and Luxury hotels. Rest assured, no matter which hotel level you’re at, our trip designers carefully select every accommodation.

Activity Level

Level 1:

Road: 1-3 hours of riding. Up to 25 mi (40 km). Up to 1,000 ft (300 m).

Gravel: 1-3 hours of riding. Up to 20 mi (35 km). Up to 1,000 ft (300 m).

Hiking: 1-3 hours of hiking. Up to 5 mi (8 km). Up to 1,000 ft (300 m).

Level 2:

Road: 2-4 hours of riding. 20-35 mi (35-60 km). Up to 2,500 ft (750 m).

Gravel: 2-4 hours of riding. 15-30 mi (25-45 km). Up to 2,000 ft (300 m).

Hiking: 2-4 hours of hiking. 4-8 mi (6-12 km). Up to 1,500 ft (450 m).

Level 3:

Road: 3-5 hours of riding. 25-55 mi (40-85 km). Up to 4,500 ft (1,500 m).

Gravel: 3-5 hours of riding. 20-40 mi (35-60 km). Up to 3,000 ft (900 m).

Hiking: 3-5 hours of hiking. 6-10 mi (9-16 km). Up to 2,000 ft (600 m).

Level 4:

Road: 4+ hours of riding. 40-70 mi (60-110 km). Up to 8,000 ft (2,400 m).

Gravel: 4+ hours of riding. 30-50 mi (45-80 km). Up to 4,000 ft (1,200 m).

Hiking: 4+ hours of hiking. 7-15 mi (11-24 km). Up to 4,000 ft (1,200 m).

What are your trip styles?

Classic - Reserve:

Savor the finer things as you relax in luxurious 5-star accommodations and wine, dine, and ride in some of the most unforgettable destinations around the world.

Classic - Signature:

Explore beautiful destinations by bike, enjoy extra inclusions, savor delicious local cuisine, and enjoy the perfect mix of accommodations.

Classic - Discover:

Enjoy a casual cycling vacation with fantastic routes and comfortable accommodations.

Ride Camp:

Train like the pros in some of their favorite riding destinations.

Pro Race:

See the pros in action at the biggest cycling events of the year.

Cross Country:

Tackle an epic adventure that takes you point-to-point across mountains, countryside, and more.

Self-Guided

Enjoy a bike tour on your schedule with just your chosen travel companions.

Single Occupancy

Sometimes it’s more convenient and comfortable to have your own room while on vacation. We understand and that’s why we offer a Single Occupancy option. The additional price guarantees a private room all to yourself