
10 Montana Towns With Unforgettable Main Streets
Flanked by false front buildings characteristic of the Old West, backdropped by commanding Rocky Mountain peaks, and flooded with happy folks who have come from all over to enjoy the fresh air and sunshine, Montana is blessed with many compelling Main Streets. Big adventures await in Big Sky Country, but before dashing to the bountiful wilderness, take a few moments, perhaps even a few days, to ground yourself in the indie coffee shops, pick up helpful tips and necessary supplies at the local outfitters, scout out the communal events, and kick back over some grass-fed grub at any of the mouth-watering eateries. These ten small towns, in particular, have the most unforgettable Main Streets in all of Montana.
Anaconda

The anomalous Montana town of Anaconda has a short but sweet commercial Main Street. Begin in Kennedy Commons (i.e. the town square park), which is where the Smeltermens Day (and Brewfest) is held each August in honor of the town's Copper industry heritage. On the east side of the road, the stately public library and arc deco Washoe Theatre invite indoor explorations. Crossing Park Ave, to the north, several appealing watering holes emerge: the Bighorn wine bar, Northern Hall Tap Room, and Smelter City Brewing. The latter has paired up with the Anaconda Taco Company food truck (both of which my palette can personally vouch for). Wherever you go, the iconic Anaconda Smoke Stack and the Anaconda Range (aka "The Pintlers") oversee it all from the periphery.
Apgar

Thinking outside the box a bit, it's hard to think of a better street to find yourself on in all of Montana than the Apgar Loop Road in Apgar Village. The plain and simple reason is that this is the southern terminus of the famed Going-to-the-Sun Road in Glacier National Park. This modest commercial stretch is where eager families, road-tripping couples, and backcountry-destined introverts all unite either right before, or in the aftermath of their epic adventures. Grab a site at Apgar Campground, or treat yourself to a room at one of the lodges, then indulge in some of the simpler pleasures offered by one of America's most beautiful landscapes. Take in the views of the incomparable Lake McDonald, walk or peddle a few miles on the Apgar Bike Path (which links with the Loop Road - rentals available on "main street"), or commemorate the occasion with a bit of guilty-pleasure souvenir shopping, perhaps at the repurposed Apgar Schoolhouse.
Bigfork

It is debatable which of Bigfork's thoroughfares constitutes its "Main Street," but I think it's fair to say that the bulk of the action concentrates on and around Electric Avenue. Here, betwixt the Bigfork Harbor (i.e. an excellent spot to launch a paddleboard into Flathead Lake - talk to Basecamp Bigfork) and the Swan River (be sure to check out the namesake trail that parallels it), the heart of of little old Bigfork beats strong and true. There are no less than six art galleries, multiple coffee shops, a few solid eateries, and lots of dealers of the gift and gadget variety. If you find yourself with a case of "The Mondays," then follow Electric Ave south and then steer toward the crowds at the River View Bar, where you'll find the live music, draft beer, barbeque, and artisan vendors of the Bigfork Monday Market.
Big Sky

The resort town of Big Sky can be divided into three parts: the Canyon, the Meadow, and the Mountain. And while the Mountain Village is the overall focal point of Big Sky (given its world class skiing and mountain biking) for the purposes of Main Street discussions, let us hone in on the Meadow Village. Surrounded by the Madison Range (a subset of the Rocky Mountains), hidden waterfalls, and, as one might suspect, verdant alpine meadows, the Meadow Village is the perfect place to experience the full spectrum of Big Sky. A stroll down Town Center Ave will get you geared up (at places like Montana Supply Co and East Slope Outdoors), caffeinated, satiated, and if you so choose, inebriated (a few rounds at Beehive Basin Brewery ought to do the trick). Whatever you do, reserve some space in your gut and liver for the Music in the Mountain series (every Thursday during the summer), which is not only a packed outdoor concert but a congregation of local food and booze vendors.
Bozeman

Home to Montana State University, the Museum of the Rockies, and a base camp for some awesome wilderness adventures, Bozeman is one of Montana's most beloved cities. Its lengthy and compelling Main Street is merely the cherry on top. Engaging by day, thanks to a healthy blend of cafes, galleries, and boutique shops, and seductive by night, owing to a wealth of saloons, eateries, and performance venues illuminated in neon, there's never a bad time to stroll down this core, reduced-speed section of I-90. If you're feeling overwhelmed by the flashy choices, start at Bacchus Pub beneath the historic Baxter Hotel (whose sign stands proudly above the flock). Or, if you do arrive during the day and want to learn more about Bozeman's Wild West and Native American history, take a tour of the Gallatin History Museum on the west end of Main Street.
Kalispell

Plunked between Bigfork and Whitefish (which we'll explore further down this list), Kalispell lacks the touristic shine of its neighbors, but because of this, it has a rustic feel that is appealing in its own right. Ironically, the impetus for the city's initial boom (i.e. the arrival of the Great Northern Railroad in the early 1890s) was soon thereafter the source of its decline (when it expanded to Whitefish, which immediately became the new hub). Thankfully, Kalispell received a new shot in the arm with the establishment of nearby Glacier National Park in 1910. As such, Main Street is lined with plenty of early 20th-century buildings, many of which have a soft beige-brick facade that gives them a unique, weathered appearance. Begin your Main Street orientation at the corner of Center Street, and then head south toward the Courthouse Historic District, taking time to peruse the antique shops, outdoor gear dealers, popular coffee houses, and eclectic eateries en route.
Livingston

The Park County town of Livingston has a designated Main Street (it's even called as such), but in practice, it's really more of a main T-intersection. Main Street itself embodies that quintessential frontier town aesthetic, thanks to its near continuous stretch of two-storey, red-brick facades. For some five blocks of its south-bound stretch, there is a refreshing blend of tourist-friendly establishments and salt-of-the-earth businesses selling everyday. Along the perpendicular Park Street, pedestrians will find the Livingston Depot Center - a circa 1902 railway station filled with exhibits. Directly across the street, The Historic Murray Hotel plunks itself next to a string of cool restaurants, a well-patroned brewery, and a few more Montana-themed shops.
Missoula

Though the biggest city on this list (by a solid margin), downtown Missoula still exhibits that relaxed, contained vibe of its contemporaries. And while this college town (home to the University of Montana) once again has a designated Main Street, personally, I would shift the focus to Higgins Ave. From the Northern Pacific Railroad Depot (where the Missoula Farmers' Market congregates on Saturday mornings and Tuesday evenings) down to Caras Park (where surfers take advantage of the static waves on the Clark Fork River), the familiar architectural string of rusty red and sandstone stylings lines the way. Note the many cafes, boutique shops, galleries, and historic structures (such as the Florence Hotel and The Wilma - a 1,000+ seat performance venue/cinema) en route.
West Yellowstone

West Yellowstone exists to service tourists heading into and out of Montana's portion of Yellowstone National Park (i.e. oldest and one of its most popular national parks in the country). And so while Canyon Street (i.e. a commercialized portion of U.S. Highway 191) can appear a bit gimmicky, it does ultimately have a quirky charm. If you're in need of a novelty t-shirt, a tank of gas, and a tried-and-true American meal, then you've come to the right place. But with those caveats aside, West Yellowstone does have one authentic, nature-based attraction: the Grizzly & Wolf Discovery Center. This open-air facility at the end of Canyon Street provides a sanctuary for not only the namesake apex predators but also frollicking otters and grounded birds of prey. Compared to your standard zoo, the Discovery Center takes in injured or habituated animals that can no longer thrive in the wild and educates the joyous onlookers about how we can best co-exist with these amazing species.
Whitefish

Whitefish is another one of those four-season Montana towns with a core cluster of well-trodden streets, rather than a definitive "Main." However, after getting in on the late summer action, I think it makes sense to highlight Central Avenue. This fun-filled north-south strip begins (or terminates) at Depot Park, where the Amtrak brings outdoorsy folks from all across the lands, the Stumptown Historical Society maintains a museum within the archaic station, and the Whitefish Farmers' Market congregates each Tuesday - bringing music, food, and hand-crafted goods into one lovely place. If the local indie artists pique your creative fancy, then keep the vibe going across the street at O'Shaughnessy Cultural Arts Center or up one block at another food truck and open-air live music hub known as Thirty Eight. Otherwise, vie for a table at any of the various brewpubs and grills, where yet more live music is almost guaranteed.
Parting Thoughts
Montana takes full advantage of its diverse seasons for outdoor recreation opportunities and creative annual events. So regardless of when you visit Big Sky Country, the epicenters of these ten towns are likely to be bumping! It is this blend of social energy and natural beauty that makes these ten Main Streets truly unforgettable.