Montana has been described as one small town with a lot of road in between. Considering the fact that our largest city has a population of 109,000, which would make it a mid-sized city, at best, in most other states, it’s safe to say that our small towns are the heart, soul, and treasure of the Treasure State. Many of our small towns have charming, enticing, and quaint downtown areas that are fantastic to explore for a day or weekend. Deciding on the very best of them is like trying to choose your favorite star in the sky – it can feel almost impossible. With that being said, we do feel like there are a few small towns that have the very best downtown areas. Check out a few of these small towns in Montana with quintessentially charming downtown scenes:

1. Livingston
Livingston, MT 59047, USA
Tracy Hunter / Flickr
Livingston's got a population of around 7,500, so it certainly isn't that tiniest town on this list. Despite the fact that, like the rest of Montana, it's growing in size, the sturdy historic structures downtown remain largely unchanged. Walking through downtown Livingston truly feels like a step back in town to the Wild West. This is such a neat town and it's particularly wonderful to check out during summer in Montana.
2. Philipsburg
Philipsburg, MT 59858, USA
Jasperdo / Flickr
Philipsburg isn't the only 19th-century mining town that you can find in Montana, but it's definitely one of the best. There's so much to do here and you'll be absolutely smitten with this great little place. Whether you're mining for sapphires, hiking all the nearby nature trails, or savoring sweets at the local old-fashioned soda fountain, there's a ton to love about Philipsburg. It's also one of the most beautiful cities in Montana.
3. Choteau
Choteau, MT 59422, USA
J. Stephen Conn / Flickr
Choteau is located in Teton County, just 20 miles east of the Rocky Mountains. This is a small city, but it's got a big heart! It's a perfect jumping-off point if you're looking to explore all the nearby natural areas that are so prevalent in this part of Montana. It also happens to be a fantastic place to spend a weekend (or a lifetime).

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4. Anaconda
Anaconda, MT, USA
Jasperdo / Flickr
Nestled in a valley in the Deer Lodge National Forest, Anaconda is an old mining town with plenty of modern appeal. The town's Main Street is a pretty place to wander, complete with plenty of historic buildings, restaurants, and shops.
5. Ennis
Ennis, MT 59729, USA
Domenico Convertini / Flickr
This tiny town was named after William Ennis, who was one of the early discoverers of gold in the nearby Alder Gulch in 1863. There's not much to this place - it's definitely a very small town. However, the downtown area here is the very definition of small town charm. This is one of the most adorable small towns in Montana.
6. Virginia City
Virginia City, MT 59729, USA
Jasperdo / Flickr
Virginia City may be a tourist town, but it's also one of the most famous living, breathing ghost towns in Montana, and it's loaded with local history. The downtown area is certainly at its liveliest in the summer, but it's a delight to visit at any time of year.
7. Havre
Havre, MT 59501, USA
Jasperdo / Flickr
Havre isn't much of a popular tourist town, but it definitely embodies small-town Montana at its very finest. It's actually the eighth-largest town in the Treasure State, but since we have so many small towns, that's not saying a lot. Havre is home to Havre Beneath the Streets, a mind-blowing underground tour. But you've gotta admit, Havre above the streets is pretty fantastic, too.

Obviously, this is far from a complete list of charming small towns downtown areas in Montana, and that’s the very best part – there are too many to choose from! Which Montana Main Street do you love the most?

 

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More to Explore

Small Towns In Montana

Lisa Sammons | September 11, 2022

What are some more of the best small towns in Montana?

The Treasure State is basically just a collection of small towns, so it's no surprise that there are many great small towns in Montana. We have so few big cities here, so the definition of a small town is a little different than it may be in other states. We have plenty of small towns here that are under 500 people! One of our favorites is Gardiner, which is just outside of Yellowstone.

What are the best small town restaurants in Montana?

Plenty of the best restaurants in Montana are located in small towns. The Grizzly Bar is in Roscoe, a tiny town in the middle of nowhere with a population of around 50 people, but it's incredibly tasty!

What are the most beautiful places in Montana?

There's no shortage of gorgeous places in Montana - after all, we're called the Treasure State for a reason! Lake McDonald in Glacier National Park is an amazing body of water that is so lovely!

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