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Your Montana adventure begins in Billings, Montana’s largest city. Depending on when you arrive, take the day to relax and ease into the time change. Grab a hearty, Montana-made meal at one of the stellar restaurants in the city’s historic downtown, and turn in early tonight at the Billings Holiday Inn Express and Suites. 

Today starts with a guided bike ride on the Rimrocks along the Skyline Trail, enjoying expansive views of the Yellowstone Valley. Scenic stops allow for photos and local storytelling about Billings’ landscape and history. The Rimrocks are one of Billings’ most striking and defining features — a dramatic line of sandstone cliffs that rise hundreds of feet above the city. From above, you can take in sweeping views of downtown Billings, the Yellowstone River Valley and endless big-sky Montana — including views of five different mountain ranges. The sandstone cliffs are the site for the highlight adventure of the day. Professional guides provide instruction before guests rappel down the Rimrocks. Participants who prefer to stay topside can enjoy a Skyline Trail walk and overlook viewpoints. Next, experience the city’s agricultural roots with a visit to Marbled, a family-run ranch located just 12 miles south of Billings. Guests will discover how this ranch controls every step of the process — breeding, feeding, harvesting and processing — to ensure exceptional flavor and unmatched quality. Back in Billings’ historic downtown, explore local shopping and craftsmanship at locally owned Western shops that showcase how that heritage lives today. A stop at Retro Cowgirl — a Western boutique, hat bar and cowgirl essentials shop — adds a fun, interactive twist to the experience. Known for their one-of-a-kind hat bar experiences, guests can design and customize their own Western hat with unique bands, brands and accents, creating a wearable souvenir that’s both personal and distinctly Montana. A visit to Rand’s Hats delivers a true Western highlight. Guests watch skilled hat makers shape and custom-fit hats — an artisan tradition that transforms a simple accessory into a personal badge of Western identity. The adventure wraps up with a toast to Billings’ brewing legacy. End the day with a tasting at a local brewery on the Billings Brew Trail, the only walkable beer trail in Montana. The trail boasts 11 breweries along with three distilleries and a cider mill.

141 mi/228 km— 2.5-hour drive

Billings and the surrounding region are rich with history, culture and breathtaking scenery, offering everything from ancient rock art and sacred Native sites to legendary battlefields and world-famous national parks. These landmarks invite visitors to step back in time and experience the stories that have shaped this remarkable land. Begin with a guided exploration of Pictograph Cave State Park, where ancient rock art created by early Indigenous peoples offers a window into thousands of years of human history. More than 100 figures, painted between 200 and 2,000 years ago, depict animals, warriors and even rifles, offering insight into the lives and stories of those who once called this region home. Then, travel east along the Yellowstone River to Pompeys Pillar, one of the most important physical records of the Lewis and Clark Expedition. Guests can walk the interpretive trail, view William Clark’s signature carved into the sandstone pillar and learn about the area’s cultural significance to the Crow Nation long before expedition journals documented it. Interpretive panels and discussion highlight Indigenous perspectives on exploration history. Make sure to pause along the Yellowstone River corridor to appreciate the landscape that sustained Native peoples for generations. Guided tours may discuss wildlife, trade routes and the river’s role in shaping settlement. Travel on to the Custer Battlefield Trading Post. Located in the heart of Crow Country, guests can enjoy Indian tTacos made with fry bread and flavorful buffalo burgers while browsing Native American art and jewelry. After lunch, continue to Little Bighorn Battlefield National Monument, one of the most significant historic sites in the American West. A ranger-led or guided experience explores the events of 1876 from multiple viewpoints, including Lakota, Cheyenne, Arapaho and U.S. Army narratives. Guests can visit the Indian Memorial and battlefield markers while learning about sovereignty, resilience and cultural legacy. After visiting the battlefield, return to Billings to rest for the evening at your hotel.

285 mi/460 km — 6.5-hour drive

Set out from Billings on a scenic 60-mile drive to the charming mountain town of Red Lodge, where guests can stroll historic downtown streets lined with boutiques, galleries and cafés. Here, a stop at Babcock & Miles offers the perfect opportunity to gather gourmet picnic supplies — artisan cheeses, fresh bread, local specialties and sweet treats — before climbing into higher country. From Red Lodge, follow the legendary Beartooth Highway, a National Scenic Byway renowned for its sweeping alpine vistas, rugged peaks and high-elevation tundra. The ascent winds past glacial lakes, dramatic switchbacks and panoramic overlooks that reveal the grandeur of the Absaroka–Beartooth Mountains. The corridor offers numerous interpretive opportunities related to geology, high alpine ecosystems and the Absaroka–Beartooth Wilderness. Wildlife viewing is common along this drive, including regular sightings of mountain goats, who thrive at elevations exceeding 13,000 feet and are often observed grazing or navigating the steep slopes and rocky outcroppings near pullouts and high-elevation sections of the roadway. Near the crest of the highway, the road descends toward Beartooth Lake, an idyllic spot for a relaxed picnic surrounded by clear waters and towering peaks. Guests can unwind lakeside, enjoy their Red Lodge provisions and take in the crisp mountain air. Continuing westward, the route passes through Cooke City and enters Yellowstone National Park via the Northeast Entrance. From here, the tour opens into the Lamar Valley, often described as the “Serengeti of North America” for its abundant wildlife and expansive, open meadows. The valley provides excellent opportunities to spot bison herds, elk, pronghorn, coyotes and, with luck, distant wolves or bears. Enjoy dinner back in Red Lodge before returning to Billings.

217 mi/350 km — 3.5-hour drive

After an easy and beautiful 3.5-hour drive, arrive in Great Falls. Here, you’ll find rich culture, a plethora of art and lots of history surrounded by unspoiled, diverse landscapes. Great Falls is often called “Montana’s Best Dam Town” thanks to the five falls and dams along the mighty Missouri River, which runs right through town. Begin your visit with dinner at The Station District, where you can experience four unique restaurant concepts and a full bar all under one roof. Each guest can choose the cuisine that suits their taste, making it a personalized dining experience for everyone. Up for a nightcap? Visit the world-famous Sip ’n Dip Lounge, home of the iconic Montana mermaids and a must-see stop in Great Falls. Named the #1 Bar Worth Flying For by GQ Magazine, this retro tiki bar is a bucket-list destination for travelers. The lounge features live music led by local favorite Joel Corda. Sing along, blow kisses to the mermaids swimming behind the glass and sip on Montana’s most famous tiki drink: the Fishbowl. End the night at the Best Western Plus Riverfront Hotel and Suites.

Today begins with breakfast catered at the Paris Gibson Square Museum of Art, a vibrant center for contemporary art and cultural programming in Great Falls. Housed in a historic building, the museum features rotating exhibitions, educational programs and community events that showcase both regional and national artists, fostering creativity and engagement for all ages. Take a tour of the current art exhibitions and then enjoy a hands-on experience with clay, learning to throw pots on the potter's wheel in a group workshop. Works will be made and reclaimed back to be thrown again another day. Then, head out to Ryan Island, a scenic island overlooking the Great Falls that offers walking trails, picnic areas and beautiful views of the Missouri River. It’s a popular spot for outdoor recreation and relaxation, providing a peaceful retreat within the heart of the city. After enjoying the vantage point, make your way back to town to step into the story of the Lewis and Clark Expedition at the Lewis and Clark Interpretive Center — North America’s most extensive collection dedicated to the Corps of Discovery. Built into a scenic bluff overlooking the iconic Missouri River, this 25,000-square-foot facility features immersive exhibits, a theater, an outdoor amphitheater, education spaces and sweeping river views. Then, enjoy a delicious dinner at 5th & Wine, a local favorite that brings together the best of wine, food and community. This vibrant spot combines a wine and beer shop, deli, stylish wine bar and full-service restaurant all under one roof. The seasonally rotating menu highlights locally grown ingredients and reflects the flavors of the region. Once you’ve finished dinner, stop for a scoop at Big Dipper Ice Cream on your way back to the hotel.

156 mi/252 km — 2.5-hour drive

Before leaving town, stop for a visit at the C.M. Russell Museum, a celebration of the life and legacy of famed Western artist Charles Marion Russell. The museum features an extensive collection of Russell’s paintings, sculptures, letters and personal artifacts, offering visitors an immersive look at the American West through the eyes of one of its most iconic storytellers. From Great Falls, head west toward Glacier National Park, stopping in Browning on the Blackfeet Indian Reservation along the way. Here, make sure to visit the Museum of the Plains Indian to engage with the history and culture of several Northern Plains tribes — including the Blackfeet — through their arts and artifacts. After, travel on to St. Mary, a charming community on the eastern side of the park. Head into the village for dinner, where you’ll find several options — both casual and upscale — for delicious Montana fare. The sun sets late in Montana, so if you’re visiting in the summertime, you won’t want to miss seeing the sunset along St. Mary Lake after dinner. Then, head to St. Mary Lodge and Resort to check in for the night.

135 mi/218 km — 2.5-hour drive

Depart St. Mary early for Apgar Village in West Glacier to begin a full day in the park. . From here, you can choose to take a Blackfeet-led tour of the park with Sun Tours or hop on one of Glacier’s famous red buses for a trip on the Going-to-the-Sun Road. The respective tours will fill the morning, so reconvene for lunch back in the Apgar Village. Then, enjoy a scenic boat tour of Lake McDonald, during which you’ll see mountain peaks and wildlife and learn about the iconic, glacier-carved lake. After your cruise, drive into nearby Kalispell and check into the Homewood Suites. Grab a quick dinner at a local restaurant and settle in for the night.

121 mi/195 km — 2.5-hour drive

Start the morning with breakfast at your hotel, and begin the journey toward Missoula. On the way, enjoy breathtaking views of Flathead Lake — the largest natural body of freshwater west of the Mississippi River. At the southern end of the lake, you’ll find Polson, a lakeside community with plenty of character. While you’re here, stop at the Miracle of America Museum to learn about the history of the United States. Then, drive on to Missoula. Nestled in the heart of western Montana, Missoula is a hidden gem that offers a perfect mix of outdoor adventure, rich cultural experiences and vibrant local flavor. Whether you’re drawn to its scenic landscapes, historic charm or artisanal food scene, Missoula offers dynamic experiences for your authentic Montana getaway. For lunch, check out one of the many options in downtown Missoula. Enjoy the patio at Cranky Sams, enjoy authentic Mexican fare at The Camino or sample the delicious rotating seasonal menu at Top Hat Lounge After lunch, head to the Rattlesnake National Recreation Area, just north of Missoula. The Rattlesnake Loop trail offers a moderate hike with incredible views of the surrounding mountains and valley. If you prefer something shorter and easier, check out Greenough Park, which features paved trails along the Rattlesnake Creek. After your hike, head back to town and enjoy a leisurely walk along the Riverfront Trail or take in the great views of the river from Caras Park. Once you check in to the Holiday Inn Missoula Downtown and freshen up for the evening, treat yourself to dinner at 1889, a steakhouse known for its delicious takes on Montana-sourced beef. After dinner, take a leisurely stroll to Montgomery Distillery for a nightcap featuring spirits distilled in Missoula.

Start with a delicious breakfast at Market on Front. We recommend the breakfast burrito, but they offer a range of breakfast options from fresh pastries to gourmet breakfast bowls, and their coffee is fantastic, too. For large groups, we recommend ordering ahead of time. Then, spend the morning learning about the history of Missoula at the Historical Museum at Fort Missoula. Located on the west side of town, the museum features exhibits about the area's Native American history, early settlers, military presence and the development of the region. The museum is located at Fort Missoula, a historic U.S. Army post, and the entire compound offers a historical feel in a beautiful setting. For lunch, we recommend checking out the Notorious P.I.G location near the fort for delicious southern-style barbeque. They have mouthwatering pulled pork or chicken sandwiches, a great variety of sides and delicious desserts. While on the western side of town, spend some time exploring some of the scenic natural areas nearby. Maclay Flats offers an easy and scenic loop, Blue Mountain's criss-crossing trail system provides many options for exploration, or head up to Pattee Canyon for a more serene outdoor experience. If you’re in the mood for some shopping, stop by Southgate Mall, where you’ll find a range of local boutiques and stores. If craft beer is your scene, Missoula is the spot for you. With over a dozen breweries to choose from, all with their own unique style and atmosphere, you have a lot of sampling to look forward to!

For dinner, make it a special experience by enjoying one of Missoula's many unique upscale establishments. Head up to The Keep for gorgeous sunset views or enjoy a pint with your meal at Tamarack Brewing Company. After dinner, head to the historic Wilma Theater and enjoy one of the many performances, from live music and comedy to independent films. Check the schedule to see what’s on during your visit. Or, take a peek at The Roxy's movie lineup and enjoy a show in this historic spot. If you’re up for one last stop, grab a drink at Western Cider, a local cidery that grows its own apples in the Bitterroot Valley. Usually bustling with locals, it’s the perfect spot to cheers to the end of your Montana adventure.

Alt Route: Fly into Missoula and end in Billings.