10-Day Group Travel Itinerary

Your Montana adventure begins in Billings, Montana’s largest city. Nestled between sandstone cliffs and the Yellowstone River, Billings blends natural beauty, Wild West heritage, and a laid-back, creative energy that makes even a whirlwind visit feel full and unhurried. 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 Hotel & Convention Center.

Start today exploring the 500-foot rimrocks towering above the city. A striking landmark, these sandstone walls rise steeply and dramatically, and scenic stops along them offer sweeping views of downtown Billings, the Yellowstone River Valley and five nearby mountain ranges. The Skyline Trail is a paved, multiuse path that makes the rimrocks more accessible for walking, biking and rappelling. A bike ride along the rimrocks is a great way to take in Billings’ signature landscape: Visitors can rent equipment from local outfitters such as The Spoke Shop, which offers bike rentals, helmets and local trail advice.

From the rimrocks, make your way to the Western Heritage Center, located in a historic 1901 library building. This local history museum is full of stories about cowboys, railroads, Native American tribes and settlers. If art is more your style, wander through the Yellowstone Art Museum, home to a dynamic collection of contemporary Western art and rotating exhibits. After a culture fix, head to The Burger Dive, an award-winning eatery known for creative, crave-worthy burgers served in a retro-cool diner setting. Here, enjoy a classic cheeseburger or something bold, like a huckleberry-Hatch chile combo.

Then, explore downtown Billings, full of boutiques and galleries for the perfect souvenirs and keepsakes. Check out local favorites like SOMETHINGchic, Cricket Clothing Co. and Frae Collective, or find a custom, heirloom-quality Western hat at D. James Western Hat Co. or Rand's Custom Hats. Other great hot spots to shop are YesterYears Antique Mall, Popover Kitchen Supply and This House of Books.

As the sun starts to get lower in the sky, grab a drink at Last Chance Pub & Cider Mill or Carter’s Brewing along the Billings Brew Trail. The Brew Trail includes 10 breweries, a winery, a cider mill and three distilleries, with many of these stops along a 1.5-mile loop through the historic downtown area. From locally brewed beers and sours to crafted ciders, wine and spirits, there’s something for everyone’s taste. Be sure to stop in at Undammed Distilling Co. and check out the Billings-only bourbon released in 2025: Pryor Creek Bourbon. This is one bourbon you won’t find outside of Billings. 

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 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 tacos 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 scenic 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 good time? Visit Great Falls’ premier entertainment venue, The Newberry. With performances from both local artists and internationally-acclaimed acts, a visit here is the best way to wrap up the evening. Check their schedule to see what’s playing during your visit. 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 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 on U.S. Highway 2 toward Glacier National Park, stopping in Browning on the Blackfeet Indian Reservation as you marvel at the Rocky Mountain Front ahead. Here, visit the Museum of the Plains Indian. Founded in 1941 and operated in partnership with the U.S. Department of the Interior, the museum preserves and interprets a rich collection of Indigenous culture. It focuses on the Northern Plains Tribal peoples, including the Flathead, Chippewa, Cree, Northern Cheyenne, Crow, Blackfeet, Assiniboine, Shoshone, Nez Perce, Sioux and Arapaho. The exhibits feature clothing, horse tack, household tools and implements, baby carriers, toys, and weapons, as well as both historic and contemporary arts and crafts. You’ll also encounter stunning, vibrant traditional regalia of Northern Plains children, women and men, alongside displays featuring art forms used in social and ceremonial aspects of culture.

Continue to St. Mary, a historic community on the eastern side of Glacier National Park. The St. Mary Visitor Center houses interesting exhibits on wildlife, geology, and Native American culture and history, as well as an auditorium featuring videos and ranger talks. Before arrival, check into their evening program schedule, including Native American Speaks, where tribal members share their knowledge, history and culture. Another option is Half the Park Happens After Dark, an astronomer-led night sky viewing activity offered on clear nights at the visitor center’s observatory, which is located in the parking lot and features a 20-inch telescope and astronomy camera. For dinner, Snowgoose Grille is recommended for delicious Montana fare. The sun sets late in Montana, so if you’re visiting in the summertime, take a leisurely sunset walk along St. Mary Lake after dinner. Get a restful sleep at St. Mary Lodge & Resort. Tomorrow, the road continues west through Glacier National Park.

135 mi/218 km — 2.5-hour drive

Depart St. Mary for a full day in Glacier National Park. You have two options for guided tours of the park (and the iconic Going-to-the-Sun Road) through park concessionaires on excursions reserved in advance. The first option is a tour with Sun Tours, told from the Blackfeet perspective. Guides are tribal members of the Blackfeet Nation and provide an all-encompassing history of the landscape, the park, animal species, common plants and roots used for nutrition and medicine, and the Blackfoot spiritual and philosophical perspectives. The other option is an iconic red bus tour. The drivers of the canvas-topped red buses — often called jammers because they had to jam the gears as they traveled the steep roads back in the 1930s — share facts about the park's landscapes, wildlife and geology. Both tours stop at Logan Pass at the Continental Divide.

Your tour will end at Lake McDonald Lodge* on Lake McDonald, the park's largest lake. Have lunch at Russell’s Fireside Dining Room as a group or a more casual lunch at Jammer Joe’s Grill & Pizza. After lunch, enjoy a historic boat tour on the DeSmet booked through Glacier Park Boat Company. Your guide will narrate the geology, the park's human history, and the ecology of the surrounding forest throughout the hour. 

In Kalispell, check into one of many hotels working with group tour operators, including Hampton Inn, Homewood Suites or SpringHill Suites. Dinner options include Freestone Restaurant, The Montana Club or Casa Luna.

*Due to length restrictions, your motorcoach will have to travel around Glacier on U.S. Highway 2 and can meet up with the group at Lake McDonald Lodge to continue your travels to Kalispell.

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 freshwater lake 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 by the Miracle of America Museum to see its artifacts and displays of Americana curiosities. Next, make your way to the Ninepipes Museum of Early Montana on the Flathead Indian Reservation. While perusing the museum, enjoy a narrated audio tour that brings each exhibit to life. A nature trail, a stop in the gift shop, and sweeping views of the Mission Mountain Range round out the visit. Enjoy lunch next door at Ninepipes Lodge's Allentown Restaurant before continuing 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. Start off your visit by heading 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 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.