14-Day Western Experiences and History Road Trip

Your Western adventure begins in Helena, where you’ll land in a capital city cradled by mountains. This small city is a hub for history, with beauty and culture in equal measure. For history buffs, make your way to the Montana Heritage Center. Newly minted in 2025, this space is the home of the Montana Historical Society and features exhibits that bring the state’s past to life. For those looking for contemporary works by Montana artists, visit the Holter Museum of Art or the renowned Archie Bray Foundation. If you’re passing through during the fourth week of July, you can’t miss the Last Chance Stampede and Fair. You’ve likely worked up an appetite at this point, so head to The Union for dinner and enjoy elevated Montana cuisine at its finest. Beef is our state’s specialty, and here you’ll find it in several delicious iterations, accompanied by fresh, locally sourced ingredients. At the end of a long day, rest your head at The Sanders, a historic bed and breakfast in one of Helena’s elegantly restored mansions. Welcoming hosts and luxurious accommodations allow you to live just as the influential Sanders family did in Helena's early days.

Today, you’ll head into southwest Montana, an area rich with history and the centuries-old stories of cowboys and miners who called this region home. Just an hour away from Helena, pull off the interstate into the small town of Deer Lodge. Here, you’ll find the Old Montana Prison Museum, where you can step into the cells once occupied by Montana’s most infamous outlaws. Then, drive east toward Anaconda, at one time a booming copper-smelting town. Though no longer operational, its smelting stack is one of the world’s tallest free-standing brick structures in the world and can be seen from Interstate 90. Once you roll in, stop by Smelter City Brewing to try a local beer, and grab lunch from Anaconda Taco Company right outside. After your pit stop, get back on the road and make your way to Butte, once the largest producer of copper in the country and still a major hub for mining culture and its legacy. Set out on one of the Old Butte Historical Adventures through — or even under — downtown to experience some of the city’s most significant sites up close, or travel underground on a mine tour at the World Museum of Mining. After exploring the largest National Historic Landmark District in the country, get a bite to eat at one of Butte’s several iconic eateries. Pick up a traditional mining-era pasty at Joe’s Pasty Shop, a pork chop sandwich from Pork Chop John’s or a no-frills burger from Matt’s Place. When you’re ready to turn in for the night, there are plenty of options for getting cozy. Between the 150-year-old Copper King Mansion, the boutique Miner’s Hotel or the Hotel Finlen — Butte’s premier downtown accommodation — there’s a room for everyone. 

Start the day’s adventures by heading into the heart of southwestern Montana. Pay a visit to Bannack State Park — it's the site of Bannack, which was the first territorial capital and is today one of the country’s best preserved ghost towns. While you’re meandering along the town’s main street, pop in and out of the 60 original structures that line its main road. If you’re visiting the third weekend in July, make sure to attend Bannack Days, a local summertime celebration complete with live music and period demonstrations. Afterward, drive east to Dillon. This small town brims with big-time charm, with a thriving downtown to keep you busy for the rest of the day. Visiting over Labor Day? Make sure to stick around for the Dillon Jaycee Rodeo. It’s part of “Montana’s Biggest Weekend,” a quintessentially Montana celebration that features a 4-H fair with local livestock, a parade and a concert. Settle in for the night at the boutique Andrus Hotel downtown. 

Head farther east and you’ll find Virginia City, a boom town that served as the territorial capital of the state for a decade. The streets of this historic community make you feel like you’ve stepped back in time. While you’re wandering, pop by Cousins Candy Store to satisfy your sweet tooth. Then, stop for lunch at Montana’s oldest bar, the Bale of Hay Saloon, to fuel up at this 140-year-old watering hole before catching an early performance by The Illustrious Virginia City Players. You can stay the night nearby at an authentic working ranch like Upper Canyon Outfitters or Centennial Guest Ranch, or drive to Bozeman for some in-town adventures. Staying at the Lark will put you in the center of the action and give you access to all Bozeman's historic Main Street has to offer. The city is home to some of the best dining in the state, and with choices like Farmer’s Daughters, Bodhi Farms, Little Star Diner and Shan serving up dishes made with fresh, local ingredients, you can get a taste of the new Western flavors that are putting our top chefs on the map.  If you’re visiting the first weekend in August, make sure to hit the Bozeman Stampede Rodeo, or visit the Valley View Rodeo most summer weekends to feel the thrill of Montana's official state sport.

Today’s adventures start with a stop in Livingston. This small town situated on the Yellowstone River at the north end of Paradise Valley is full of life, and with artists of all kinds in abundance, this is a community bursting with creativity and an impressive number of locally owned shops lining the downtown streets. As you pull in, head to Gil’s Goods and tuck in to some all-American fare. Grab a seat in the conjoining Murray Bar — a local spot once visited by Anthony Bourdain — and pair your lunch with a craft beer or cocktail. Then hit the road for Big Timber, where you can visit the Crazy Mountain Museum. Specializing in the history of Sweet Grass County, the museum displays artifacts that help to tell the story of the area. After your museum visit, enjoy a steak dinner in the newly restored dining room of the Grand Hotel. End the night in nearby Greycliff, where you can sleep inside one of Greycliff Mill’s remodeled grain silos with views of the Yellowstone River. Before calling it a day, make sure to stop by the property’s market to pick up some local goods. 

Pack up and hit the road toward Red Lodge and ultimately Cooke City. If you’re passing through on a Friday, Saturday or Sunday, stop in Fishtail for lunch at MontAsia, an eclectic hometown spot with a James Beard-nominated head chef. Serving American-Asian fusion cuisine, their dishes welcome visitors to sample the unique flavors. After lunch, drive south to the charming mountain village of Red Lodge. At the mouth of the Beartooth Mountains, this small town is Montana to its core. Wander Broadway Avenue to peruse the local shops selling all kinds of items, from kitschy trinkets to luxury goods. After you’ve shopped for the perfect mementoes of your Montana travels, hop back in the car to drive the famous Beartooth Highway, known as one of the country’s most beautiful roads. As you climb above the treeline, you’ll be met with panoramic views of the breathtaking alpine peaks. End the day of adventures at Skyline Guest Ranch outside of Cooke City, where you’ll spend the next two days exploring the surrounding wilderness. Enjoy a home-cooked meal prepared with locally sourced ingredients by their on-site chefs, and unwind among the peaceful mountain scenery. 

Spend the day trekking across mountainsides on horseback on an excursion with Skyline Guest Ranch. While traversing the rocky terrain, experience sweeping views of the Beartooth Range, wildflower-studded meadows and waterfalls. With the help of your horse — and an experienced guide — you’ll climb to 10,000 feet in elevation for an unparalleled perspective of the nearby peaks. After a full day outdoors, return to the ranch for an incredible home-cooked meal, and turn in for the night. 

For your final day on the ranch, travel into Yellowstone National Park to explore the Lamar Valley — also known as “America’s Serengeti” — by way of the Skyline Safari. As one of the park’s best places for wildlife viewing, expect to see bison, pronghorn, coyotes, bears, wolves and even more of Yellowstone's most iconic animals roaming in their natural habitat. For your last night at Skyline Guest Ranch, arrive back on the grounds in time for one more delicious meal, and reminisce on the adventure of a lifetime.

Get an early start to make your way to Billings, the largest city in Montana. From there, you have two options for how to spend your day. The first option is to sightsee in and around Billings. This industrial, cultural and economic hub offers big-city amenities and is bordered by the Yellowstone River, which offers plentiful recreation in, around and on the waterway. There are plenty of things to do here, with the hardest choice being where to begin. Regardless of what you choose, make sure to grab a burger from The Burger Dive. This award-winning local favorite serves up some of the best burgers in the region and is a stop on the Southeast Montana Burger Trail. If you’re feeling like a beer is in order, set out on the Billings Brew Trail — Montana’s largest walkable brewery trail, with six breweries, two distilleries and one cider mill. Up for learning some history? Visit Pictograph Cave State Park or Pompeys Pillar National Monument, both of which offer a chance to experience the story of Montana up close and feature interpretive visitor centers and signage. If a museum afternoon is more your speed, head to the Western Heritage Center, a museum focused on the history of Billings and the surrounding region, or the Moss Mansion Museum, a grand home built by Billings entrepreneur Preston Boyd Moss in 1903 that today spotlights turn-of-the-20th-century Billings culture and development. 

Your other option is to visit sites southeast of Billings on the Crow Reservation, home of the Apsáalooke (Crow) Nation. In Crow Agency, you’ll find the Little Bighorn Battlefield National Monument, which commemorates the most influential battle of the Plains Indian Wars. (Be sure to check operating hours before you visit.) If you’re visiting Crow Agency the third week in June, the Crow Native Days celebration is a can’t-miss event, and if you’re passing through in mid-August, the Crow Fair and Rodeo is the event of the summer for the region. About an hour south of Crow Agency, you’ll reach Fort Smith and the North District of the breathtaking Bighorn Canyon National Recreation Area. This is a great destination for fishing, boating — rentals are available at Ok-A-Beh Marina — and simply enjoying the scenery, including not only the dramatic canyon walls but also the impressive Yellowtail Dam a little ways upriver. Make your way back to Billings and stop at Chief Plenty Coups State Park along the way. The park preserves the log home, farmstead and sacred spring of the last traditional Crow chief, who helped his people adapt to the changes sweeping the West in the late 1800s and early 1900s. Once back in Billings, settle in for the night at the four-star Northern Hotel.

For those wanting to embrace their inner cowboy, look no further than Miles City. Today, you’ll arrive in town around lunchtime, and you’d be remiss not to make your way to June’s Bungalow for some grub. Another stop on the Southeast Montana Burger Trail, this spot features unique flavor combinations like the Mango Burger, with mango salsa, guacamole and havarti cheese. After lunch, walk the streets of downtown Miles City and pop into the shops that dot the thoroughfare. To shop local Western wear, make sure to stop into the Miles City Saddlery. Then, head to the Range Riders Museum to learn about the history of the area. From dinosaurs to pioneers, this hometown treasure is the heart of the community’s historical collection. If you’re in town the third weekend in May, be sure to check out the Bucking Horse Sale, a local tradition that kicks off the summer rodeo season for the whole state and is a highlight of the year. When it’s time to call it a night, pull into the Motel Miles for some shut-eye. 

Set your GPS to Glendive this morning to experience the majesty of Makoshika State Park — Montana’s largest state park and home to fossil remains of Tyrannosaurus rex, Triceratops and other prehistoric life. The towering sandstone badlands offer unique scenery that is full of year-round recreation opportunities. From biking and hiking to camping under a star-filled sky, there are endless ways to enjoy the area. After you’ve worked up an appetite, head into Glendive proper for a lunch at Bloom and Vine. This beloved local spot offers delicious coffee and fresh sandwiches inside a historic greenhouse. Spend the afternoon stopping into the eclectic shops of downtown Glendive, and end the day with dancing at the Wagon Wheel Bar — a local hangout with food, drinks and live entertainment. Tonight, you’ll get some well-deserved rest at the Glendive Lodge. 

Today’s adventures take you across the state line as you venture into North Dakota to visit Theodore Roosevelt National Park. The park’s namesake president once had a ranch here and its rugged badlands are home to plentiful wildlife. A sunset out here is not to be missed, as the sky is painted shades of pink and purple and the bluffs turn to gold. If you’re visiting after July 2026, make sure to pay a visit to the brand-new Theodore Roosevelt Presidential Library in nearby Medora. This architectural marvel will embrace the beauty of the surrounding landscape while educating about Roosevelt’s devotion to preserving the natural world. Overnight in Medora at the Conestoga Wagons or Ferris Inn. 

For your last day of exploring, head into Bismarck, the state’s capital. Here, you can visit the historic capitol building as well as the North Dakota Heritage Center and State Museum to learn more about the history of North Dakota. Then, visit Fort Abraham Lincoln State Park and On-A-Slant Village for insight into the Mandan Native Americans who inhabited the area, and tour the earthlodges, blockhouses and barracks of the fort. Finally, head to the Bismarck Hotel for the last night of your two-week-long adventure of a lifetime. 

Fly out of Bismarck, North Dakota.