We love small-town living here in Montana. And it isn’t hard to find something positive about each of our communities, big or small. But there are some towns that seem to have more character than could possibly fit into their borders… and if you spend enough time there, you’ll fall in love. Without further ado, here are 11 charming small towns in Montana that will absolutely steal your heart.

1. Choteau
david / Flickr
Our list of the most charming small towns in Montana begins in Choteau. Choteau is the kind of place you go for a getaway and decide to stay... just ask David Letterman, who visited and ended up buying a ranch in the area. But even if you're not a California celebrity, the allure of this little city is undeniable. Here's more on why Choteau might just be the most underrated small town in Montana.
2. Fort Benton
J. Stephen Conn / Flickr
The history, the dining, the museums, the Bridge to Nowhere, the Missouri River... what's not to love about the Birthplace of Montana? It's a truly incredible place. Here's more on what makes Fort Benton such a charming small town in Montana.
3. Red Lodge
Frank DiBona / Flickr
Red Lodge Mountain is a very popular place for snow sports, but the area also has so much more to offer. From hiking and wildlife viewing to shopping and delicious dining, it's easy to see why people love it. Learn more about planning a visit to Red Lodge, Montana.
4. Dillon
J. Stephen Conn / Flickr
Nestled in a sweeping valley into which the Beaverhead, Big Hole and Ruby Rivers drain, Dillon is a laid back little city that about 4,000 people call home. Walking through the downtown area feels like going back in time to the gold rush days, and the fact that it's near Bannack State Park doesn't hurt. The town of Dillonhas a little something for everyone.
5. Havre
Eric O'Brien / Flickr
This welcoming sign alone shows what a friendly place Havre can be. This rural agricultural community is a year-round retreat for nature lovers, recreation enthusiasts and history buffs. The underground city alone, Havre Beneath the Streets, makes it a place worth visiting.

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6. Cut Bank
Jimmy Emerson, DVM / Flickr
Any place that welcomes visitors with a giant talking penguin statue is certainly worthy of our adoration. And while it might seem like a mere pitstop on the way to Glacier National Park, it's actually a pretty great place to live. While you're there, be sure to check out this incredible Montana steakhouse.
7. Ennis
Spend A Day Touring, LLC / Flickr
When you spend time in Ennis, you'll soon realize you're surrounded by art, both the man-made kind (sculptures and galleries) and natural wonders like the Madison Mountains. But whether it's paintings or landscapes that inspires you, you must admit this place makes a beautiful muse for creativity.
8. Cooke City
Pattys-photos / Flickr
Cooke City offers a "best of both worlds" way of living; not only will you enjoy peace and quiet in this town of 140, but because it's a Gateway to Yellowstone National Park, you'll also find some good restaurants and shops meant to attract tourists.
9. Big Sky
Garen M. / Flickr
The Big Sky Resort attracts hundreds and hundreds of tourists a year, but the charm of the town - not to mention its close proximity to natural wonders like Ousel Falls - is what makes people fall in love with it. If you really want to be charmed by Big Sky, go during the holiday season and check out all the Christmas lights. Here's more on why Big Sky is one of the coolest towns in Montana.
10. Troy
Scott Butner / Flickr
Is it the picturesque surroundings, the friendly people or the town amenities themselves that make Troy, called the Gateway to Montana, so charming? We're not sure, but it's easy to leave a little piece of your heart in Troy. Plus, while you're there, you'll be close to the largest waterfall in Montana!
11. Philipsburg
USDARD LAPAS / Flickr
Last but not least on our list of the most charming small towns in Montana is Philipsburg. Philipsburg has become a very popular vacation destination for Montanans, and it's easy to see why. You can mine for sapphires, do some shopping and have dessert at an old-fashioned soda fountain in the same day.

We love paying homage to our beautiful, charming small towns in Montana. If you don’t see your favorite one on the list, perhaps it’s on this list of some of our most charming quiet communities.

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More to Explore

charming small towns in Montana

Beth C. | August 05, 2021

What are some other small towns to explore in Montana?

There are so many charming small towns in Montana, that it's difficult to include them all in one list! If you're curious about some other fun destinations to explore, there are plenty of additional towns that belong on your radar. Some of these include Chinook, Plains, Wibaux, Fairview, Jordan, Sheridan, Hardin, and Cameron. You can learn more about these destinations by reading our previous article: Here Are The 9 Coolest Small Towns In Montana You've Probably Never Heard Of.

Does Montana have any natural wonders?

Absolutely! The state of Montana itself could be characterized as a natural wonder, given the abundance of beauty to see at every turn. Some of the most incredible natural wonders in Montana include Glacier National Park, Humbug Spires Wilderness Study Area, Kootenai Falls, Flathead Lake, Bighorn Canyon National Recreation Area, Makoshika State Park, Gates of the Mountains, Bob Marshall Wilderness Area, Quake Lake, and Lewis & Clark Caverns. Learn more about these must-see natural wonders in Montana.

Are there any haunted small towns in Montana?

While many of Montana's towns are filled with charm, there are plenty of others that have been downright abandoned. Some of the creepiest ghost towns in Montana include Garnet, Elkhorn, Montana City, Bannack, Castle Town, Coloma, Hell Gate, and Taft. Have you ever explored any of these abandoned ghost towns in Montana?

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Featured Addresses
Fort Benton, MT 59442, USA
Red Lodge, MT 59068, USA
Dillon, MT 59725, USA
Havre, MT 59501, USA
Cut Bank, MT 59427, USA
Ennis, MT 59729, USA
Cooke City-Silver Gate, MT, USA
Big Sky, MT, USA
Troy, MT 59935, USA
Philipsburg, MT 59858, USA
100 1st St NW, Choteau, MT 59422, USA