11 Most Charming Cities in Montana

Montana, the fourth largest state by area, is one of the true wonders of the western United States. With vast expanses of wilderness, diverse natural beauty, wide open skies and a wealth of fascinating history, Montana is an adventure just waiting to be experienced. Whether it’s ranching, camping, skiing, horseback riding or discovering gold rush history, Montana truly is Big Sky Country with lots of fun for any vacation or residence. This article looks at the 11 most charming towns in Montana.

West Yellowstone

Aerial view of the tourist mecca of West Yellowstone, which borders directly on the west entrance of the national park.

West Yellowstone, a city of 1,300, borders Yellowstone National Park and is the ideal place to quickly reach the famous park. Founded at the turn of the 20th century as a railroad town, West Yellowstone is now primarily a stopover destination, but offers great Montana charm and hospitality. Tourists can enjoy quaint and delicious local restaurants, shops, boutiques, and local galleries, while a stay at the Grizzly & Wolf Discovery Center allows visitors to spot local wildlife outside of Yellowstone Park.


The Teton River with Ear Mountain in the fall at sunrise near Choteau, Montana
The Teton River with Ear Mountain in the fall at sunrise near Choteau, Montana.

Choteau is about 20 miles east of the Rocky Mountains and borders Flathead National Forest. It is surrounded by trees, mountain peaks and ranches. Near Egg Mountain, an important dinosaur paleontology site, visitors can stop by the Old Trail Museum to see interactive exhibits and a variety of dinosaur skeletons on display. The seat of Teton County, visitors to Choteau can also enjoy great hiking, scenic drives, hot summer sun and Montana’s famous big sky in a quiet and peaceful community.


Main Street in Whitefish, Montana
Main Street in Whitefish, Montana. Editorial Credit: Beeldtype / Shutterstock.com

Located in Flathead County, the town of Whitefish is recognized as one of the top ski resorts in the United States, where visitors can enjoy great runs like those at Whitefish Mountain Resort. Just a 35-minute drive from Glacier National Park, tourists can also take advantage of great fly-fishing and hiking opportunities. For the arts enthusiast, Whitefish offers a wealth of great festivals throughout the year including the Food Festival “taste of whitefish”, “Big Sky Music Festival” and the “White Fish Winter Carnival.”


Historic downtown Livingston near Yellowstone National Park
Historic downtown Livingston near Yellowstone National Park. Editorial Credit: Nick Fox / Shutterstock.com

Livingston is a beautiful and quaint mountain town located on the Yellowstone River in southwest Montana and adjacent to Yellowstone National Park. Enjoy breathtaking views of Livingston Peak, enjoy hiking and biking trails, or simply stroll downtown. A visit to the historic Livingston Depot (a former 1902 train station) takes tourists back to the glorious past of steam engines, while several 19th-century buildings line Main Street. A quaint and charming community, Livingston is a great snapshot of anytown with a uniquely Montana flavor.


Kootenai Falls on the Kootenai River, Lincoln County, Montana
Kootenai Falls on the Kootenai River, Lincoln County, Montana.

Libby is a stunning place to experience Montana’s natural beauty. Located at the confluence of the Kootenai River and Libby Creek, visitors can fish for trout or sturgeon, or hike the many mountain trails surrounding it. Stop at Kootenai Falls for great views of the rushing water and maybe a sight of black bears and bighorn sheep. And of course, a hike across the Swinging Bridge is sure to create a memory that will be talked about for years to come.

big sky

Big Sky, Montana
Big Sky, Montana.

With moderate temperatures year-round, Big Sky is an ideal place for outdoor activities in both winter and summer. It is a mountain community and home to Big Sky Resort, the second largest ski area in the United States. Capture incredible views of the Rocky Mountains and enjoy world-class skiing, or head to the Chalet for a beautiful alpine atmosphere. The nearby Gallatin National Forest and river is perfect for hiking, biking, camping, rafting and fly fishing in the summer months. As the name suggests, the time spent in this community shows exactly why Montana is “Land of the Big Sky”.


A view of the rural town of Philipsburg, Montana
A view of the rural town of Philipsburg, Montana.

With a population of just 841, Philipsburg is a charming snapshot of a once-prosperous 19th-century mining town. Visit several historic buildings that still dot downtown today, including the Sayrs Building, built in 1888, or enjoy local hiking trails before stopping for a pint at Philipsburg Brewing Company. To take home a unique piece of Montana, visitors can find an abundance of sapphires and other gemstones at many local boutiques, meaning a part of Philipsburg is always with you.


Historic St. Mary's Mission in Stevensville, Montana
Historic St. Mary’s Mission in Stevensville, Montana.

Founded in 1841 by Jesuit missionaries, Stevensville is notable for being the first non-Indigenous settlement in the entire state. Surrounded by majestic mountain ranges, including the Sapphire and Bitterroot Mountains, a drive through and stopover in Stevensville offers some of Montana’s most beautiful scenery. For history buffs, a visit to the Stevensville Museum (detailing the founding and growth of the community) and historic St. Mary’s Mission are places of interest that shed light on America’s expansion in the 19th century.


With hot summers and mild winters, Hamilton in Ravalli County is a great destination along Highway 93 for a mix of history, outdoor fun and delicious local food. Stroll through the charming downtown area and see the Daly Mansion, an example of 20th-century Revival-style architecture, and its lush green courtyard. Biking and hiking opportunities abound at nearby Trapper Peak, while a locally prepared Montana dinner is always served on Main Street by the welcoming residents.

Fort Benton

Historic Fort Benton and Fort Benton Bridge, Montana
Historic Fort Benton and Fort Benton Bridge, Montana. Editorial Credit: Joseph Sohm / Shutterstock.com

The county seat of Chouteau County, the 1,500-person town of Fort Benton was founded in 1846 and is the second-oldest non-Indigenous settlement in the state after Stevensville. A key site on the banks of the Missouri River, Fort Benson was established as a fur trading post and played a critical role in the growth of the American West. This waterfront and fort area was designated a National Historic Landmark in 1961. Visitors can enjoy a first-hand look at preserved 19th-century buildings, outposts, and museums dedicated to the period. And of course there’s also the opportunity to hike, camp and canoe in typical Montana fashion.


Anaconda Smelter Stack in Montana
Anaconda Smelter Stack in Montana.

Perched at the base of the Anaconda mountain range, a stop in the town of Anaconda is the best place for breathtaking views and easy access to these majestic land formations. Anaconda is also a rich cultural city with lots of value and is perfect for many outdoor adventures like rock climbing, hiking and camping. Visit the historic Washoe Theater (built 1931), listed on the National Register of Historic Places in 1988, or the famous Club Moderne bar, built in 1937. A stroll through downtown Anaconda is filled with beautiful Western-inspired facades, while its moderate year-round climate makes it a desirable place to relax at any time of the year.

Montana is known as Big Sky Country, and with its wealth of natural beauty and fascinating history, it’s clear that the opportunities for discovery are as numerous as the open sky. These small towns each offer the best the state has to offer outside of the big cities, and a visit to one of them showcases not only the charm of small town USA, but also the unique appeal of Montana and its beauty.

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