The 10 Best Small Towns in Montana to Retire

Rebecca Hanlon
Last Updated: March 4th, 2023

Montana has some of the best scenery in the country, including Glacier National Park and parts of Yellowstone National Park.  The mountains, lakes, rivers, and prairies combine to make the Big Sky state a four-season delight to visit. As such, the scenic landscape offers plenty of options for the best small towns in Montana to retire in.

Apart from the attraction of vacationing here, I wondered what it might be like to retire here, however, not in a city environment but in one of the historic small towns that are scattered across the state, something with less than 10,000 people.

I wanted to know which of these might have the best combination of historic charm, amenities, friendly community, and access to outdoor activities that would make them appealing for retirees.

The 10 Best Small Towns in Montana For Retirement

  1. Whitefish
  2. Hamilton
  3. Polson
  4. Choteau
  5. East Helena
  6. Anaconda
  7. Dillon
  8. Belgrade
  9. Livingston
  10. Lewistown

1. Whitefish


Whitefish is one of the best ski towns in the country, surrounded by the majestic Rocky Mountains, located just 25 miles from Glacier National Park and the same distance north of the city of Kalispell.

Named one of the “Top 25 Ski Towns in the World” by National Geographic, Whitefish is situated at the base of Whitefish Mountain Resort, the second largest ski area in the state. Visitors can enjoy skiing and snowboarding on over 3,000 acres.

Whitefish also features the beautiful Whitefish Lake right at the edge of town for boating and fishing, as well as a state park and the Flathead National Forest.  There are plenty of scenic trails for hiking and mountain biking.

Whitefish’s single main street, Central Avenue, is lined with restaurants, coffee shops, art galleries, gift shops, and clothing stores, and the town has its own theater. Special annual events include Huckleberry Days in summer and the Winter Carnival.

2. Hamilton


The small town of Hamilton is in the western part of Montana, nestled between two mountain ranges in the Bitterroot Valley and about one hour south of Missoula. Hamilton is one of the 10 best small towns to retire in the United States according to Travel and Leisure magazine.

From outdoor recreation to in-town dining and entertainment, historic Hamilton offers a little something for everyone. The Bitterroot River runs through Hamilton and the valley is surrounded by beautiful mountain ranges. Fishing, hiking, camping, and skiing are all close by in Hamilton.

Founded in 1890, the town has several striking, historic buildings, including the Daly Mansion built for one of Montana’s “Copper Kings” and the Old Ravalli County Courthouse from 1900. The historic streets are full of character and charm.

3. Polson


Polson lies on the southern shore of Flathead Lake in northwestern Montana, about 70 miles north of Missoula. It is bordered to the south by the Mission Mountains, providing a gorgeous setting for this charming town.

The shoreline of Flathead Lake stretches for miles on the horizon. Boating and fishing are abundant on the water and camping and picnicking are available on its shores. The Flathead River that flows from Polson features whitewater rafting.

Polson offers several interesting museums plus a golf course and has a good selection of local restaurants and shops. It has vast cherry orchards, celebrated every year in July with a Cherry Festival.

4. Choteau


Choteau is another charming small Montana town at the foot of the Rocky Mountains, located about 1 hour northwest of Great Falls.

Several attractive locally owned shops and diners are to be found in the quaint downtown. It’s also home to one of the most important fossil finds in the world, discovered in the nearby Egg Mountain, which can be viewed in a 3D display at the town’s Old Trail Museum.

The Two Medicine Dinosaur Center in nearby Bynum is the place to get more insights into the region’s dinosaur legacy.

Just outside of town is the Bob Marshall Wilderness, a million or more acres ideal for outdoor activities. Camping, swimming, hiking, fishing, golf, and horseback riding are popular during the summer, while winter activities include skiing or snowmobiling.

5. East Helena

east helena

The small town of East Helena is located roughly 5 miles east of downtown Helena, giving its residents easy access to the state capital’s wide array of amenities.

East Helena abounds with recreational opportunities on Holter, Hauser, and Canyon Ferry Lakes, which were all formed by dams on the Missouri River.

The town is a vibrant community with events such as the East Helena rodeo, and its Fourth of July fireworks show.

6. Anaconda


Anaconda is in southwest Montana, 25 miles west of Butte, and is surrounded by mountains, lakes, and forests.  Anaconda traces its history back to the days of copper smelting, beginning in the early 1900s. Visitors get a closer look at this history at the Anaconda Smokestack State Park.

Outdoor recreational activities include boating, fishing, ice skating, golf, and hiking at places such as Georgetown Lake and the surrounding Deer Lodge National Forest. The dramatic cliffs and geological formations of nearby Lost Creek State Park are also worth exploring.

Historic downtown Anaconda features some buildings dating back to the late 1800s, such as the Hearst Free Library and the Deer Lodge County Courthouse.

The town has four historic districts lined with antique Western facades. The Washoe Theater in Anaconda is particularly noteworthy, with its historic Art Deco design.

7. Dillon


With its history and outdoor attractions, Dillon is an excellent place for retirees, situated about one hour south of Butte. The town is set in a sweeping valley into which the Ruby, Big Hole and Beaverhead rivers drain.

The town is home to a blue-ribbon trout stream with some of the best fly fishing in the country. There are nearby hiking trails through beautiful surroundings, both cross country and downhill skiing and PRCA rodeo weekends.

Dillon has several interesting museums preserving local history such as the Beaverhead County Museum. There is also Bannack State Park, site of the first gold strike in Montana, and the most well-preserved ghost town in the state.

8. Belgrade


Situated 10 miles northwest of Bozeman, in the center of Gallatin Valley, Belgrade provides convenient access to attractions such as the Bridger Bowl, Big Sky Resort, and Yellowstone National Park which are located a short drive away.

You can hike, raft, mountain bike, backpack and go horseback riding in the surrounding mountains.  Spend an afternoon biking or walking the 4.5-mile Valley Center Trail. The Lewis and Clark Caverns and the Museum of the Rockies are all within close driving distance.

Belgrade has a variety of nice restaurants as well as plenty of in-town attractions such as golf courses, skating rinks, parks, theaters, country clubs and a special events center. Don’t miss the Belgrade Community Market, a local farmers market showcasing some of the finest local products.

9. Livingston


Livingston is 25 miles east of Bozeman and 45 miles from the northern entrance to Yellowstone National Park.

There is a Fly-Fishing Discovery Center, given the town’s popularity as a fly-fishing center. It is surrounded by four mountain ranges that offer abundant outdoor activities year-round, from horseback riding and river rafting to dog sledding or cross-country skiing.

Livingston has plenty of typical Montana charm. The downtown streets are lined with restaurants, art galleries, bars, and saloons. Historic buildings include the Livingston Depot, a former train station that dates to 1902 and now contains a museum of Montana railroad history. The Yellowstone Gateway Museum is another good place to learn about the area.

You can also enjoy annual events like the Livingston Roundup Rodeo.

10. Lewistown


Located in the very center of Montana about two hours north of Billings, Lewistown is an agricultural community in the vast Judith Basin. Where the mountains and plains meet. Here you’ll find an outdoor recreation paradise, including fishing, hiking, skiing, and biking.

Although mostly characterized by rolling prairie, farms, and ranches, the Lewistown area features five beautiful mountain ranges from which panoramic vistas stretch to the horizon.

Annual celebrations include the summer Chokecherry Festival and Central Montana Fair. Music on Main is another enjoyable summer diversion that takes place downtown every Wednesday.

These small towns have retained much of their historic Old West feel and western charm. The abundance of outdoor recreational activities, town amenities, and community bonds make any of these 10 towns great choices for those looking to retire in the beautiful state of Montana.

About The Author

Rebecca Hanlon

Rebecca has been a travel blogger and editor for over 5 years, working with some of the biggest brands in industry. She’s taught English as a foreign language in 5 different countries, and her most fulfilling role was as a tour guide around some of Europe’s finest vineyards. She the one behind the social channels here at Discovering Montana, whilst also finding the time to perform an assistant editor role.

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