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.

18-23 miles & 1,500-2,300′

Accommodations: The Pollard Hotel

We start the morning with a quick shuttle to the beginning of our ride. From there, the route carries us to the foot of the Beartooth Wilderness Area, where the views are nothing short of spectacular. The valley feels like a step back in time, offering a rare glimpse into Montana’s rich and rugged past.

We’ll wrap up the ride at the Tippet Art Center, an incredible venue set on a historic ranch that has been thoughtfully transformed into a vibrant hub for art and culture. The center features large-scale sculptures, rotating exhibitions, and thoughtfully curated installations that blend seamlessly with the surrounding landscape. With its mix of contemporary art and Western heritage, it offers a unique and inspiring setting for relaxing, exploring, and reflecting on the day’s ride. Our Chefs will prepare a picnic lunch, and we will shuttle back to Red Lodge by van.

55 miles & 3,200′

Accommodations: The Pollard Hotel

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 ride is reminiscent of the Galibier, a famous Tour de France stage, with most of the climb above the tree line. Once we top out at just shy of 11,000 feet, it’s mostly downhill for the next 20 miles, and you will lose 4,000 feet. Guests can choose to stop at mile 50 or continue on to Cooke City for the additional 15 miles and 1,500 feet. We will ride this section the next day in the opposite direction. 

The final miles will take us back into Montana and our final resting place at Cooke City, which sits at 7,500 feet.

Beartooth Pass (East)

50-65 miles & 6,000 – 7,500′

Accommodations: High Country Motel Cabins

The Chief Joseph Scenic Byway follows the route taken by the Nez Perce tribe as they fled the US Cavalry in 1877. We pass several 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 surrounded by forests. The route tops out at 8,048 feet. We will have a picnic lunch at the summit before flipping it to enjoy the descent off Chief Joseph back towards Cooke City. At the bottom of the pass, we will shuttle by van back to Cooke City.

55 miles & 4,400

Accommodations: High Country Motel and Cabins

A beautiful point-to-point ride from Gardiner to Chico along the historic Old Yellowstone Trail, this route rolls gently north through Paradise Valley with the Yellowstone River never far from view. The terrain is mostly gradual with a few steady rises, and traffic is typically light, making for a relaxed and scenic day in the saddle. Big mountain views, open ranch land, and the quiet backroad feel make this a classic Montana ride, finishing with a well-earned soak or meal at Chico.

40 miles & 1,500′

Accommodations: Chico Hot Springs

Today’s ride begins in Paradise Valley, rolling north from Chico through wide-open ranch land with sweeping views of the Absaroka Range before turning west toward the Gallatin Valley. The terrain is mostly gradual early on, giving way to a steady climb as you approach Bridger Canyon, where the road winds through pine forest and offers a true Montana mountain pass feel. After cresting the canyon, enjoy a rewarding descent into Bozeman, finishing with big views of the Bridger Range and a lively town atmosphere. A classic local ride that blends valley cruising with a memorable mountain crossing.

55 miles & 2,600′

Accommodations: TBD

Shuttles will run to Bozeman International Airport (BZN) and local hotels all morning, with the last shuttle leaving at 11 a.m.

Today’s plan: Departure Day

We’ll be running shuttles to the Bozeman airport (BZN) and hotels. The last shuttle leaves at 11 a.m.