21 Best Kept Secret Places to Retire in Montana

This is an aerial panoramic next the Higgins Street Bridge in Missoula, Montana on a beautiful fall day in Western Montana. You can see the M on Mount Sentinel and L on Mount Jumbo.
Keegan Connell/Shutterstock.com

Written by Samuel Christopher

Published: November 15, 2023

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Montana is possibly the most rugged and beautiful state in the lower 48. Appropriately nicknamed “Big Sky Country,” this state boasts various terrains and topographies ranging from the Great Plains to the towering Rockies.

Montana is also generally fairly affordable as far as the United States goes. This makes it an excellent choice for retirement for those looking to spend a lot of time in the great outdoors in their golden years.

If you’re curious about retirement life in the great open west, take a look at this list of some of the best under-the-radar spots you can stake your tent in, so to speak.

 1. Seeley Lake

Fishing on Seeley Lake Montana

An angler drops his line in Seeley Lake.

Seeley Lake is a delightful little lake town located on the nominal Seeley Lake. The village is located about two hours north of the city of Missoula and about three hours south of Glacier National Park.

Seeley Lake boasts some of the best fishing in the state. It is also within distance of some vast wilderness areas that offer endless opportunities for camping and backpacking. The town is named after an early pioneer, Jasper B. Seeley. Seeley served as the first forest ranger for the nearby Flathead National Forest.

2. Polson

Polson Montana on a sunny day

Polson and the stunning Mission Mountains.

This place is a small lakeside city on Montana’s iconic Flathead Lake, the largest freshwater lake west of the Mississippi River. The city and Flathead offer endless opportunities for outdoor activities. In addition, they also offer access to learning more about the indigenous people of the region, the Flathead.

The city and Flathead Lake are shadowed by the nearby Mission Mountains, which cut a dramatic edge into the sky. Beyond the Mission Mountains lies the Bob Marshall Wilderness, which boasts some of the densest concentrations of wildlife in the lower 48. This is the kind of area where daredevils head to test their wills against a fierce wilderness.

3. Missoula

Man Fishes on Blockfoot River in Montana

Missoula is mentioned in many films and works of literature.

This entry is a sweet college city nestled in a geographical region known as the Five Valleys. This is a confluence of several different mountain ranges that all terminate in the valley that the city of Missoula is built upon.

The city boasts a high quality of life, as well as a little bit of a cultural edge, thanks to the local college, the University of Montana. The idyllic city has been featured in several films and books, including A River Runs Through It.

This place makes a great retirement option in Montana if you’re interested in having just a hint of the city life in the great wilds of Montana. It’s not much, but it’s just enough to get you through some snowy winters.

4. Bozeman

Bozeman, Montana

Montana State University in downtown Bozeman.

Bozeman is a small college city that has a heavily outdoor-focused lifestyle. Extreme sports are so huge in this small city, partially due to the abundance of hiking, skiing, rafting, and other sporting options nearby.

Bozeman is also not far from Yellowstone National Park, one of the best places in the country for viewing some epic North American megafauna. In addition, you can spend some time observing some of the intense geothermal activity that occurs in this region.

Bozeman’s advantages are quickly being noticed. As of the early 2020s, this city is the fastest-growing metropolitan area in Montana.

5. Helena

Drone view of the Montana State Capitol, in Helena, on a sunny afternoon with hazy sky caused by wildfires. The Montana State Capitol houses the Montana State Legislature.

The Montana State Capital in Helena.

Helena is the capital of Montana and boasts a number of different cultural and outdoor options for the people who live there. For those interested in the politics of this sparsely-populated state, this city is where the state senate convenes.

At the turn of the century, Helena was home to a disproportionately high number of millionaires. This is due to the fact that many miners who struck it rich in Montana’s gold and copper rush resettled in the city. This, in turn, resulted in the construction of many elaborate Victorian Mansions in the region. This means that if you’re an architecture geek, this might be a place that you find interest in.

Helena is also notable for the amount of sun it receives compared to many other places in Western Montana.

6. The Bitterroot

Western Montana, Bitterroot Mountain Sunset

The valley and mountains at dusk.

This area is just south of Missoula and boasts epic views of the surrounding mountain range, the Bitterroot Mountains.

These mountains offer avid outdoors people the chance of a lifetime to challenge themselves with some rugged outdoor backcountry hikes. On top of this, the communities that exist in the valley (such as Hamilton) offer residents a slice of authentic Montana life. Being that it’s not far away from Missoula, access to modern amenities isn’t as much of a challenge as it is in some of the more remote parts of Montana.

7. Havre

A golden wheat field in Havre, Montana.

Havre is close to major wheat production centers in Montana.

This here is a tiny little hamlet way out east in the Great Plains section of the state. This off-the-map gem is a great little place to live if you’re interested in having a little more sunshine than in the western half of the state.

This tiny community offers much for its small size — for one, the small city offers some of the biggest-sky big sky views available in the big sky state. Due to the fact that it’s located on the Great Plains, there aren’t as many mountains to crowd out the fantastic sunsets.

Agricultural enthusiasts can find another point of interest nearby as well. The world’s largest tractor, Big Bud 747, lives on the outskirts of the city.

8. Miles City

Alpenglow on badlands mountain cliffs in Eastern Montana during sunrise, near Miles City, MT

The Badlands of Eastern Montana at dusk.

Miles City is another eastern gem. It’s one that offers residents a plethora of sporting activities and water fun due to its proximity to the Yellowstone River.

History buffs will find much to enjoy in Miles City. The city’s origins lie in the aftermath of the Battle of the Little Bighorn. After the battle, the United States Army set up a series of forts in Eastern Montana following the violence. Much of this historical architecture still stands in the downtown of the city.

Those who prefer a more arid climate will also enjoy Miles City. The city lies close to an area of Badlands, a unique type of semi-arid terrain that peppers the desert west and Great Plains areas.

9. Hot Springs

Fairmont Natural Hot Springs (Fairmont, British Columbia, Canada)

There are many natural hot springs in Montana.

Hot Springs, MT, has some great hot springs, but that’s not much of a surprise. The Hot Springs that the town of Hot Springs is built around also have a very high mineral content. Frequent visitors swear by in terms of their ability to heal what ails you.

Hot Springs has the advantageous quality of being in close proximity to Flathead Lake. This aforementioned lake also provides the backdrop for Polson and Kalispell.

10. Choteau

The Teton River with Ear Mountain in autumn at sunrise near Choteau, Montana, USA

The Rocky Mountains meet the Great Plains near Choteau.

Choteau is a beautiful little western community right along the Rocky Mountain Front. This is a region where the Great Plains hit the Rocky Mountains. This makes for some extremely dramatic scenery, as the topography of the plains and meadows crashes against the power of the Rockies.

Choteau offers visitors and residents a genuine look at the life of a Westerner. Western cultural mainstays such as rodeos and steak cookouts often occur, inciting a festive atmosphere. Choteau is named after the French fur trapper and explorer Pierre Choteau. Choteau was a trapper who traveled through this part of North America in the 1800’s.

11. Kalispell

Beautiful Landscape photography of Glacier National Park in Montana USA

Kalispell is one of the gateways to Glacier National Park.

This town is a small city on the northern edge of Flathead Lake. It boasts the additional advantage of being within spitting distance of Glacier National Park as well. Also within an arm’s reach is the Bob Marshall Wilderness and the Jewel Basin, home to the lower 48’s highest concentration of Grizzly Bears.

Kalispell offers all manner of outdoor activities and has built a culture around facilitating them. The city derives its name from the Salish-Kootenai word meaning “flat land above the lake.”

The area has fostered some notable individuals in the realms of sports and the arts. Brad Bird, Lily Gladstone, and Michelle Williams all hail from this petite mountain city.

12. Fort Peck

Lovely day paddling around Fort Peck, Montana

Fort Peck Lake offers many opportunities for water recreation.

Here comes another Eastern Montana gem. This small city derives its appeal from the wide open plains it is surrounded by, as well as its proximity to the massive Fort Peck Lake reservoir. Like many of the entries of this list located in Eastern Montana, the town is very affordable, adding to its appeal as a place to retire.

The area also features a bevy of historical architecture in its downtown area. This offers visitors and residents chances to check out some of the aesthetics surrounding the Old West, decades and centuries past. Many of the buildings in its downtown are registered in the National Registry of Historic Places.

This community will carry heavy appeal to those who like to spend their days boating and their nights in a crowded saloon.

13. Chico

Chico Hot Springs. Montana on a map.

Chico Hot Springs is one of the main attractions in Chico.

This area is a tiny community that exists in a place called Paradise Valley. If you ever have the chance to go, you’ll likely find out why this valley has earned that name.

On its way to Yellowstone National Park, one of the main attractions of the area is the fabulous Chico Hot Springs resort. This humble yet refined hot spring resort features lodging and refreshments at the foot of the fantastic Bear Tooth mountains. This picturesque mountain range serves as the gateway to the wilderness area of the same name.

14. Big Sky

Scenic view of the snow covered peaks and slopes at Big Sky Ski Resort in Montana on a sunny winter day

Big Sky Ski Resort in the winter.

This entry is a ski resort census-designated place that lies 40 miles southeast of Bozeman. The community boasts two of the most popular ski resort towns in Montana: Big Sky Ski Resort and Moonlight Basin.

Given this, those who have a hunger for outdoor winter sports will likely find a lot to love about this town. In addition, the presence of multiple dude ranches in the surrounding area will likely appeal to those who have an affection for country western culture.

Aside from this, its proximity to Yellowstone also offers residents regular chances to observe North American Megafauna. Examples include animals like Moose (Alces alces) and Grey Wolves (Canis lupus).

15. Dillon

Road in Snowy Dillon Montana

A snowy country road on the outskirts of Dillon.

Dillon is a humble little community down Highway 15, close to the Continental Divide. This is the part of the Rockies that “splits” America down the middle.

Dillon began its life as a railroad town, and elements of this history are interspersed in the aesthetics and culture that it hosts. This is most apparent in its downtown historic district, which displays the architecture of the Old West for anyone interested.

Nowadays, river rafting, hiking, cross-country skiing, and hiking all serve the residents of Dillon opportunities to enjoy their days. The downhill skiing mecca Maverick Mountain Ski Area is close by, drawing tourists to Dillon to enjoy its historic charm.

16. Pony

Clouds form over the Tobacco Roots Mountains during sunset in Montana

The Tobacco Root Mountains with a dusting of snow.

Pony, MT, is the perfect choice for those interested in getting away from it all in their golden years. In some ways, this is true for the state of Montana as a whole, but Pony is one of those places where this sentiment is especially true. In terms of best-kept secrets, this one might top the list.

Pony is a census-designated place deep in the Tobacco Root mountains, a rather remote wilderness area a few hours south of Highway 90. This is the main highway that connects Montana from east to west.

One of the main points of interest in Pony is the legendary Pony Bar, named one of the country’s best bars. This bar draws in some tourists, and certainly the locals, for a taste of some authentic Montana binge drinking. Pony’s remote wilderness aspects will appeal to those who have a taste for adventure – and for great bars.

17. Paradise Valley

scenic winter landscape on a sunny day  at mallard's rest fishing access along the paradise valley scenic loop of the yellowstone river and gallatin range, south of livingston, montana

Paradise Valley is one of the gateways to Yellowstone National Park.

This one’s for those with a little money to spend. Paradise is well known for being a center for Los Angeles celebrities to buy ranches to escape the stresses of the sprawling southern California city. However, once you visit Paradise, it quickly becomes apparent why — it is absolutely gorgeous.

Paradise has a cornucopia of outdoor activities available for those who are interested. However, it’s perhaps most famous for its fabulous fly fishing. The nearby Yellow River has many fishable trout and other major game fish.

One of the famous residents who has recently “retired” to the Paradise Valley is singer-songwriter John Mayer. This pop star moved to this stunning Montana Valley in order to escape from some of the pressures of his recording career.

18. Livingston

The gateway to Yellowstone, Livingston, Montana

An alpine scene outside of Livingston.

Livingston is another historical gem in Central Montana. It has historically served as the “Gateway to Yellowstone,” as the town lies only an hour north of the entrance to the park.

Livingston’s historic downtown has over 17 places registered in the National Registry of Historic Places. On top of this, the city has found favor with some of the rich and famous as a place to lay their hat. Luminaries such as Peter Fonda, Jim Harrison, and Rich Hall have called the city home.

The lore of Livingston has even made its way into popular music – singer-songwriter Jimmy Buffett mentions this town in numerous songs.

19. Whitefish

Drone view of Whitefish lake in Montana

An aerial view over Whitefish Lake.

Whitefish is another costly option — but if you’ve got the money, it’s hard to beat. This small town is smack dab in some of the most beautiful country in the nation. It offers easy access to both Glacier National Park, as well as some of the more remote wilderness areas of Northwestern Montana.

Also of easy access is Whitefish Lake, which offers visitors a fabulous combination of water activities and amazing views. Swimmers are offered visuals of the surrounding mountains towering over the lake.

Whitefish is also home to a healthy environmental movement. The town has protected many of the lakes and streams surrounding its borders in order to preserve the quality of its water.

20. Great Falls

City lights of Great Falls, Montana over the Missouri River.

Downtown Great Falls at night.

Great Falls is another hidden gem in Eastern Montana. This highly historical city has a long history of serving truckers and railroad workers. However, it is a haven for Montana residents seeking more sunshine than the average amount in the state.

Downtown Great Falls offers a nice look at some of the historical Western architecture of this region. It also offers a visit to one of the state’s most notorious watering holes — the legendary swim-up bar, the Sip ‘N Dip. At this truly surreal bar, mermaids serve you drinks poolside while you listen to Frank Sinatra covers from a live piano player. What better way to live out your golden years?

Like most places in Montana, one of the great draws of Great Falls is its proximity to fabulous outdoor opportunities. There are several large wilderness and national forest areas in very close proximity to the park.

21. Jackson

Highway to Jackson Montana

Gorgeous alpine scenery surrounds the town.

This entry is another beautiful small Montana town. This one sits in a valley in between two gorgeous mountain ranges, the Pioneers and the Beaverheads. If you’re into small communities, this place might be right up your alley — only 36 people live in the town year-round.

One of the area’s biggest draws is its fabulous hot springs resorts. These offer residents a chance to unwind and relax in some seriously beautiful scenery despite the somewhat frigid winters of the region. The hot springs also offer lodging in a small hotel if you’re just visiting.

If you’re into outdoor activities, there’s nothing lacking in the region, as the small town is in between a few different mountain ranges.

Summary of the 21 Best Kept Secret Places to Retire in Montana

NumberName
1Seeley Lake
2Polson
3Missoula
4Bozeman
5Helena
6The Bitterroot
7Havre
8Miles City
9Hot Springs
10Choteau
11Kalispell
12Fort Peck
13Chico
14Big Sky
15Dillon
16Pony
17Paradise Valley
18Livingston
19Whitefish
20Great Falls
21Jackson


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