Overview

Today marks your first day in the sagebrush hills of the true American West. Your guides will meet you at the trip's first hotel, Best Western Premier Ivy Inn and Suites in Cody, at 11:00 AM. After quick introductions, you'll head to a shady grove on the shore of Beck Lake for a signature Trek Travel picnic, then get fitted to your bike and briefed on some safety tips and the route before heading out on your warm-up ride in the ranchlands around Cody. The terrain shifts as you ride, a mellow path around the lake giving way to smooth dirt roads, then rugged two-track climbing through the rolling hills. You'll look out over the Bighorn Basin's high desert, framed by distant peaks, before a paved descent back to the hotel. Cody, founded by William "Buffalo Bill" Cody, the frontier scout and showman who brought the American West to the world stage, is yours to explore this afternoon, a chance to live out your own visions of the wild West. Guides lead the group into town tonight for a social hour of introductions and a toast to the miles still to come, followed by dinner.

Overview

This morning, a 20-minute shuttle out of Cody delivers you to the start of the Chief Joseph Scenic Byway, a hidden gem that should be on every cyclist's bucket list. Designated one of only 184 National Scenic Byways, this road traces the journey of Chief Joseph and the Nez Perce as they fled toward Canada in 1877. Today's ride is entirely paved. Leaving the sagebrush hills behind, settle in for a challenging 12-mile climb past red rock plateaus and out of the Bighorn Basin toward the high alpine. Cresting the pass reveals stunning views of the jagged Absaroka Range in the distance and the Clarks Fork of the Yellowstone River below. Pause to savor the view before descending the flowy switchbacks down into Sunlight Basin. At the bottom, you'll cross the Sunlight Gorge Bridge, the highest bridge in Wyoming at 285 feet above the creek below. The stunning landscape continues as the road meanders through the valley, roughly tracing the Clarks Fork of the Yellowstone River, where you'll stop along the way for a bite to eat. A roadside lunch of locally made Mediterranean-style sandwiches hits the spot before you climb again past ranches and remote cabins into thinning mountain air. Tonight's stay is a small motel in Cooke City, Montana, once a remote mining camp and now a sleepy gateway to Yellowstone. Walk the town's handful of shops, then head to dinner at a time that suits you, at the Miners Saloon just across the street, full of old-West character.

Overview

Leaving Cooke City, you'll take on one of the defining rides of the trip - the Beartooth Highway. Another 100% paved day starts with a swift descent; you'll climb through 21 miles of stunning scenery toward Beartooth Pass. The road rises past alpine lakes and rocky summits before the trees fall away into windswept tundra at nearly 11,000 feet in elevation, one of the highest paved passes in the country. As the road climbs above the tree line, you'll take in views stretching across the Absaroka and Beartooth ranges, revealing the full scale of the Northern Rockies. Lunch is a casual picnic served at altitude, with the range spread out around you. After reaching the summit, you'll be rewarded with a long descent along broad switchbacks, dropping from rugged alpine terrain into Montana's open valleys below. The terrain eases into meadows and ranch land as you roll into Red Lodge, then settle in for two nights at Rock Creek Resort. Gather with the group this evening for dinner on a deck perched right at the water's edge, celebrating a hard-earned crossing of one of the West's most celebrated mountain passes. Later, unwind with the creek running just outside your window.

Overview

Red Lodge and Rock Creek Resort are yours to explore however you like today. Those eager for more time in the saddle can take a scenic loop through prairie coulees and rolling ranch land surrounding town, revealing a different side of Montana where wide-open spaces stretch toward familiar mountain horizons. Guests who choose to stay off the bike can take advantage of the resort's outdoor offerings, arranging a guided fly-fishing excursion or a naturalist-led hike through the area's wildlife and native plants, with local history woven throughout. Lunch is on your own today, with a range of guide recommendations to choose from. Riders will stop in Red Lodge for lunch before cycling the seven miles back to the resort. Those not riding can arrange the resort's shuttle into town, where shops, galleries and cafes await. Spend the afternoon easing into the creekside sauna, with dinner enjoyed at the resort at your leisure to close out the day.
Please note: Activities offered by the lodge are not included in the trip price. We recommend booking at least a week in advance, as same-day availability is limited.

Overview

Leaving Rock Creek, you have another big day in the saddle with much less elevation gain. You'll ride north through open prairies and rolling coulees, mountain ranges rising along the horizon for much of the day. Backcountry dirt roads wind through ranch country, a side of Montana defined by big skies and rugged living. Lunch today is on route in a quiet community park along the way. The terrain shifts into a dramatic canyon carved by Bridger Creek, where rising rock walls and flowing water contrast sharply with the morning's broad grasslands. The ride ends at Greycliff Mill, somewhere unexpected. This 19th-century, water-powered gristmill and barn, both relocated from the East Coast, now anchor a working homestead with a cheese cave, leather and weaving shops, and a market selling goods made on-site. Wander the grounds before your guides shuttle you about 45 minutes into Livingston, a railroad-era town that's long drawn artists and anglers to its banks along the Yellowstone River. Your home for tonight is the historic Murray Hotel, located in the center of town. With dinner on your own tonight, explore downtown, which is filled with galleries, cafés, and plenty of local character. Your guides are happy to point you toward their favorite spots.

Overview

After enjoying your final cup of morning coffee at the Murray, you'll head south from Livingston along the river into the breathtaking Paradise Valley. The ride begins on the Yellowstone River Trail before turning to gravel and climbing toward the top of a ridge, with the Gallatin Range and the now-familiar Absaroka Range framing the route all the way toward Bozeman. Halfway through, you’ll drop into Bridger Canyon, a verdant, sweeping stretch and a local favorite, riding a rollercoaster of pavement into town. Once you've settled in at The LARK, located on Main Street, head out to enjoy lunch on your own and perhaps some shopping too! This evening, reconvene with the group for social hour at Sky Shed, a glass-walled rooftop spot looking upon the Bridger Mountains. Trade stories from your week of adventure, celebrating a well-earned finish, before heading out for a farm-to-table dinner, a local specialty rooted in the valley's ranches and farms.

Overview

Breakfast this morning is just across the street from the hotel, fueling one final loop through Sypes Canyon, with panoramic views back over the valley below. It's a rolling, easy spin, a last look at the peaks you've spent the week climbing. Back at the hotel, freshen up and say goodbye to your guides after an incredible week of cycling in the Rockies.