9 Most Charming Cities in Montana

Nicknamed “the Treasure State,” because of its rich gold and silver deposits, the 41st state to join the Union easily lives up to its telling moniker: a state of endless treasures. Largely unexplored until the Lewis & Clark expedition, Montana today boasts a delightful array of attractions including Glacier National Park, a behemoth of a park that spans more than a million acres and contains some of the finest handiworks of nature. Sandwiched between Canada in the north and Wyoming and Idaho in the south, Montana is home to several cities, albeit not big—many of which will seem like a revelation. 

Whitefish

If one has to pick only one city in Montana to visit, and that is regardless of size, it will have to be Whitefish. There are several reasons Whitefish, a charming city of about 10,000 that is nestled on the western side of the continental divide — is worth backpacking for. For starters, Montana’s 9th largest city is a premier ski destination. Home to Whitefish Mountain Resort, a 3,000-acre marvel that in 2020 came third in SKI Magazine’s overall best resort in North America, Whitefish is a skier’s dream destination. In the words of SKI Magazine, this Montana gem is “arguably the most authentic ski town in sight of lift towers.” Whitefish also boasts a beautiful downtown area. The town’s historic Railway District is lined with quaint stores that shoppers will want to explore. But perhaps more importantly, Whitefish is the gateway to the Glacier National Park.

Bozeman

Boasting a population of about 57,400, Bozeman is Mntana’s 4th largest city. Set in the backdrop of a spectacular Rocky Mountain landscape, Bozeman, as with many cities in Montana, is a town that a nature lover will never complain about. Yet Bozeman’s outdoor offerings are downright unbelievable. Gallatin National Forest, for instance, a short drive from town, is a hiker’s wonderland that few alternatives can hold a candle to. There is also the Hyalite-Porcupine-Buffalo Horn Wilderness Study Area, an unbroken wilderness that is home to several marvels including Palisade Falls. For those who want to cool down after a sweat-inducing excursion, the Bozeman Hot Springs is located about 8 miles from town. And with Montana State University within its confines, Bozeman is never a dull city.

Kalispell

The city of Kalispell is nestled on the picturesque Flathead Valley near the shores of Flathead Lake. With the exception of Alaska, Flathead Lake is the largest natural freshwater lake in the western US by surface area. Boasting a population of about 29,400, Kalispell comes up at number 7—with respect to the largest cities in the Big Sky Country. Known for its cowboy life, visitors to Kalispell will get an amazing collection of cowboy regalia: boots, hats, and all—at the Western Outdoor on Main Street, the largest Western outfitter in Montana. That done, grab a sumptuous bite at the Kalispell Grand Hotel located next door, whose stone walls predate the Great Depression by more than a decade. As to outdoors, rev up the engine for Lone Pine State Park, a 270-acre marvel which offers amazing opportunities for hiking, biking, and many other things in between. 

Missoula

Boasting a population of about 76,500, Missoula is the second-largest city in Montana. Known as Zootown, this Montana gem sits on the banks of the picturesque Clark Fork River, the largest river by volume in Montana. Whether one will want to explore Missoula’s downtown area, soak in its prominent 19th-century architecture, sample its craft breweries, sate a craving in its many inviting restaurants, or just wander about, Missoula’s attractions are nearly inexhaustible. One can start by trying out traditional German food at Bayern Brewing, the oldest brewery in Montana; lace up for Mount Sentinel, a small mountain that provides an amazing bird’s eye view of the University of Montana, or venture an hour north to the Rattlesnake National Recreation Area—or even the Rattlesnake Wilderness— a postcard-perfect expanse characterized by several scenic lakes and forested ridges.

Helena

Although natives had roamed the Helena Vally many years before Europeans in what was once a vast, formidable expanse, Helena had largely remained unexplored. That is until four gold prospectors, incorrectly called “the Four Georgians,” would chance on a find that lay on the banks of a stream near where the town presently sits. A gold rush would start in earnest, drawing fortune seekers from across the nation. Today, history buffs can literally retrace Helena’s gold-rush history by strolling through Last Chance Gulch road, the exact course of the gold-laden stream which birthed Montana’s capital. Boasting a population of about 34,600, Helena's faded glory still shines through in its many 19th-century mansions — including the beautiful Cathedral of St. Helena, whose patron never lived to see the building completed.

Butte

The 5th largest city in Montana that is nestled on the western slope of the Continental Divide boasts a population of about 35,200. Named for Big Butte, the town’s most significant natural landmark that geologists believe to be the eroded neck of an extinct volcano, Butte began as a gold mining camp. It should not be a surprise. Locals called the geological formation that lent the town its name “the richest hill on earth.” The rich mineral deposits around the area would soon spur the town to its golden age. While minerals no longer attract people, Butte is home to one of the largest National Historic Landmark Districts in the United States — one that spans nearly 10,000 acres. According to the Thrillist, the 19th-century Copper King Mansion, featuring Romanesque Revival Victorian architecture, is the most beautiful building in the Big Sky Country.

Billings

Montana’s largest city is interestingly the only one that boasts a population of more than 100,000. A famous access point to Yellowstone National Park, Billings is a city that should be on every traveler’s bucket list. Billings is also just about an hour’s drive to the Little Bighorn Battlefield National Monument which memorializes the most decisive Native American victory in the long Plains Indian War. Movie lovers will want to check out Babcock Theater, a beautiful, historic theater in downtown Billings which offers an overwhelming aesthetic experience. For nature lovers, the fact Billings is encircled —not by two—but by seven mountain ranges obviously makes it worth backpacking for. That is not to mention the many ghost caves and the pretty beaches at Lake Elmo State Park.

Great Falls

Nestled along the Missouri River near the thundering 96-foot fall that lends the town its name, Great Falls is surrounded by both nature’s handcrafted charm and man-made draws in delightfully copious amounts. Boasting a population of about 60,300, Great Falls is Montana’s third-largest city. Other than the stunningly numerous outdoor options, including the beautiful Gibson Park, the nearly 60-mile-long River's Edge Trail, and the Electric City Water Park, it will be a lifetime regret to come to Great Falls and fail to check out the Sip ’N Dip Lounge located at 17 7th St S. For perspective, Artful Living declared Sip ’N Dip one of the five most extraordinary bars in the world. On the flip side, USA Today once ranked it among the ten best tiki bars in the United States.

Livingston

This southwestern Montana town hugs the picturesque Yellowstone River and was the original gateway to Yellowstone National Park. Home to about 8,700 residents, Livingston strikes the sweet spot between small-town look and big-city conveniences, complete with a blend of suburban feel and rustic charm. Noticeably authentic, with a distinctive Old West look, Livingston is encircled by snow-capped peaks and a heart-ravishing grandeur that often leaves first-time visitors in awe. It is just this stunning backdrop that would inspire celebrated American actor Robert Redford to pick Livingston as the setting of  A River Runs Through It—which would go on to win the Academy Award for Best Cinematography. For art lovers, Livingston boasts arguably the highest number of creatives per capita than even New York City.

The Takeaway

Montana’s cities are not as populated as those of New York, California, or even Texas. Only one of its cities, Billings, boasts a population of more than 100,000. Yet that is not to say that Montana’s cities are less charming. In reality, because of their low population, they could just be more charming — than their more-populated counterparts in other states. From Bozeman, to Helena, to Livingston, charm just seems to be the watchword of every Montana city.