Beartooth Road
Epic climbs in Montana and Wyoming
Climb, climb, climb throughout Montana and Wyoming.
When you think of Montana, most people envision Glacier National Park or Yellowstone National Park. But it’s a big state full of hidden treasures. One of those treasures is Red Lodge, Montana. Several years ago, we introduced the Beartooth Pass ride to our Glacier/Yellowstone routes and it quickly became a staff and guest favorite. We are super excited to introduce our newest Montana road cycling trip that features Beartooth Pass—which you get to ride from both directions.
Do you like to climb? If so, this is the trip for you. We recently introduced four-night trips, and this adventure falls into that category. You get a great elevation bang for your buck. Each day (minus the arrival day spin) has 5,000 feet or more climbing. We will have a few options to shorten rides, but if climbing isn’t what you love, you might want to consider a different trip.
Check out our Glacier National Park trips.
Highlights
- Four days of guided, supported rides through Montana and Wyoming
- Comfortable motel or lodge accommodations for four nights
- Chef-prepared or local restaurant meals each day featuring Montana produce and baked goods
- Enjoy epic bucket-list climbs in Montana and Wyoming
- Arrival Day airport and hotel pickups in Billings (BIL)
- Departure Day airport and hotel drop-offs in Billings (BIL)
Food
You’ll eat a combination of Cycling House chef-prepared meals and food at our favorite local restaurants. We prioritize locally-sourced ingredients, visiting farmers’ markets and partnering with local producers whenever possible. The Cycling House will cover all meals, snacks, and ride nutrition.
Accommodations
We start our trip in Red Lodge and stay at The Pollard Hotel for two nights. After Red Lodge, we spend one night at the High Country Motel and Cabins in Cooke City. Our final night will be spent back at The Pollard Hotel.
The Pollard was established in 1893 and is located in the heart of downtown Red Lodge. The charming hotel has a rich history and friendly staff that will make you feel at home. Our team will stay right around the corner, and our staff house will be where we serve up delicious home-cooked meals, meet for rides, and enjoy time off the bike.
ITINERARIES
Beartooth Getaway 4 Nights
Welcome to Montana - Arrival Day
Guests will arrive in Montana, and our staff will do Billings (BIL) and hotel pickups. After you register, we will email a list of suggested hotels for guests planning to arrive early. Please email us your arrival/departure plans, including flight numbers.
Everyone will have time to settle into the accomodations and enjoy our first chef-prepared meal.
After lunch, our mechanics will work on building guest bikes or fitting people to their rentals. We will depart for an afternoon shakeout spin once all the bikes are ready, and all the guests have arrived.
Our ride is an out-and-back that will give us a taste of what lies ahead on Beartooth Pass. Once we arrive back at The Pollard Hotel, we will have time to relax before our camp briefing and introductions before dinner.
Beartooth Pass (East)
Beartooth Pass is a proper bucket-list ride! The ride starts in Montana and crosses into Wyoming, climbing many hairpin turns to the summit at 10,947 feet before circling back into Montana. You’ll get spectacular views of the Absaroka-Beartooth Wilderness, home to 25 peaks soaring over 12,000 feet. The climb is worth the effort; you get views in both directions since it’s out-and-back. The ride is reminiscent of the Galibier, a famous route in the Tour de France, with most of the climb above the tree line.
Chief Joseph Scenic Byway
Today, we move out of The Pollard and depart for a 1-hour shuttle to start the ride. The Chief Joseph Scenic Byway follows the route taken by the Nez Perce tribe as they fled the US Calvary in 1877. We pass serveral interpretive sites and signs that describe the events that transpired.
History aside, the route includes stunning views of the North Absaroka and Beartooth mountains. Water abounds in the Clarks Fork of the Yellowstone River and passes through scenic valleys surronded by forests. At 13 miles into the ride, the route tops out at 8,048 feet and features rolling terrain until we intersect with Highway 212, Beartooth Pass. The route is challenging and we will have an option to shuttle into Cooke City after mile 45. The next day’s route will cover these same miles in the opposite direction as we tackle Beartooth Pass from the West.
The final miles will take us back into Montana and our final resting place at Cooke City which sits at 7,500 feet. Tonight we will celebrate yet another epic day of riding in the mountains of Montana and Wyoming and prepare for our last big ride!
Today’s Ride: Chief Joseph Scenic Byway
45-60 miles & 4,000- 7,000′
Accommodations: High Country Motel and Cabins
Beartooth Pass (West)
Today we start from Cooke City and enjoy a net loss for the first 14 miles before we start to climb Beartooth Pass from the West. Over the next 21 miles we will climb 4,300 with an average grade of 4.3%. Along the way we will pass Top of the World store, but don’t be deceived, there is still more climbing to the summit which sits just shy of 11,000 feet.
The final 30 miles are almost all downhill. We covered this same terrain two days ago—this descent is one that’s well worth doing twice! This ride climbs 5,500 feet but overall the ride is a net loss, losing 7,500 feet in total. The final descent is the perfect way to celebrate an epic few days of riding in Montana and Wyoming.
Adiós - Departure Day
Shuttles will run to Billings International Airport (BIL) and local hotels all morning, with the last shuttle leaving at 11 a.m.
The shuttle to Billings takes 1 hour and 15 minutes. If you book the earliest flight out of Billings, it will be a 4 a.m. departure. Please email us your travel plans once you make your reservations.
Today’s plan: Departure Day
We’ll be running shuttles to the Billings airport and hotels (BIL). The last shuttle leaves at 11 a.m.
DATES & PRICES
- 2026
-
Jul 8 - 12 Road Cycling$3,545 / Person Many Spots Available
DETAILS
What's Included
- Four nights/five days accommodations (double occupancy)
- All meals (breakfast, lunch, dinner)
- Mechanical support (including bike build and breakdown)
- Professional trip guides
- Daily sag support
- Ride nutrition products
- High-quality ride photos
- Arrival Day airport and hotel pickups from Billings International (BIL)
- Departure Day airport and hotel drop-offs to Billings (BIL)
What’s Not Included
- Airfare
- Bike rentals
- Café stops
- Gratuity for guides
- Personal shopping
Optional Activities
- Lake swims
- Hiking
- Yard games
Questions?
BIKE OPTIONS
Rent A Bike
Traveling through the airport with a bike—and paying for it to fly—is not everyone’s idea of a fun way to start a vacation. Fortunately, we offer high-quality, full carbon bikes on all of our trips across the United States and Europe. Want to just show up and ride? Just bring your shoes, pedals, helmet, and saddle (if you want), and rent one of ours.
Bring Your Own
Your bike is yours—we get it. Bringing your own bike has obvious advantages in terms of individual comfort. Before your trip, we suggest getting a tune-up at your local bike shop so it’s ready to roll for your week of riding. Once you arrive, we’ll be sure to have our mechanics build it and help with any necessary tweaks. Check out some helpful resources here:
Skip The Bike
If you or your travel partner want to enjoy the trip and explore a new destination without a bike, drop us a line and we’ll discuss options. Some trips are better suited for non-rider participants than others.
