Whitefish is one of our most tourist-friendly cities, and the downtown area is positively enchanting, especially with the mountainous backdrop.
Bozeman's lengthy Main Street is lined with historic structures, old and new eateries, and charming shops. It makes for a delightful stroll through town, especially during the holiday season, when the streets are lined with lights and decor.
3. Red Lodge
Set against the backdrop of the Beartooths, Red Lodge's Broadway Avenue is part of the Main Street to Mountains Rocky Fork Trail. No wonder this little city was named one of the Best Small Towns in America.
4. Miles City
Home to the historic Montana Bar as well as other shops, restaurants and cafes, Miles City's Main Street is a great place to spend an afternoon.
Known as the place where the mountains meet the plains, Lewistown is a highly underrated city -- especially their charming and walkable Main Street.
If you've never spent time in historic downtown Kalispell, you're really missing out. The juxtaposition of old and new businesses is delightful, and the Kalispell Downtown Association is always hosting events, like art walks and ladies' nights out.
It's no secret that this lakeside down is an amazing little vacation spot. And Bigfork's Electric Avenue is especially enticing thanks to its abundance of art galleries, restaurants, and mom and pop shops.
Glendive's Merrill Avenue Historic District feels like stepping into a time capsule. Among the century-old buildings you'll find Glendive City Hall and plenty of small businesses like the notorious Beer Jug.
9. Big Timber
The small town of Big Timber doesn't see much action, but when you need some interaction (or some BBQ), all you have to do is hit McLeod Street.