West Yellowstone, Montana / USA - September 28 2018: Shops along Canyon Street

11 Cutest Small Towns in Montana

Montana may be having the slowest internet speeds in the United States—after West Virginia—but internet speeds aside, the 41st state boasts a number of cute, small towns whose slow pace are doubtless among their best features. With a terrain that is excitingly diverse: with high plains on the eastern side, a rugged mountainscape on the western side, all interspersed with several heart-stirring bluffs and rivers, Montana’s small towns are just as diverse — and provide access to some of the state’s best-kept secrets. From Whitefish, an outdoor haven regarded as the official gateway to the Glacier National Park, to Glendive, a former railroad town that is home to beautiful, totem-like rock formations, Montana’s small towns are a package of pleasure. Read on to discover the 11 cutest small towns in the Big Sky Country, as Montana is affectionately called.

Whitefish

Mainstreet in Whitefish still has a smalltown feel to it, via Beeldtype / Shutterstock.com
Mainstreet in Whitefish still has a smalltown feel to it, via Beeldtype / Shutterstock.com

Boasting a population of about 10,000, Whitefish is secreted in the northwest corner of the state, right on the picturesque banks of the sparkling lake that bears its name. Regardless of the season, Whitefish, Montana will ever be choke-full of exciting adventures. This gem of a town is not unknown in ski circles. No less an authority than National Geographic, for instance, once named it among the top 25 ski towns—not in the United States—but in the world. Resplendent in its rough-hewn character, complete with sylvan charm on every side, Whitefish is the gateway to Glacier National Park. For its impressive mountain scenery, Glacier National Park is aptly nicknamed “the Crown of the Continent.” Straddling the town’s funscape like a colossus is the unparalleled Whitefish Mountain Resort. And with an international airport only 15 minutes from town, traveling to Whitefish is a cinch.

Red Lodge

Downtown streets of the small tourist town of Red Lodge, just outside of the Beartooth Highway, via melissamn / Shutterstock.com
Downtown streets of the small tourist town of Red Lodge, just outside of the Beartooth Highway, via melissamn / Shutterstock.com

Charmingly curled up in Montana’s spectacular Beartooth Mountains and encircled by as stunning a landscape as the Custer-Gallatin National Forest, Red Lodge is hands-down one of the cutest small towns in Montana. And it is not just the town, with its dazzling array of exciting offerings. Many regard the drive from Red Lodge to Yellowstone National Park through the Beartooth Highway as among the most picturesque drives on the planet. While the town boasts a population of only about 2,500, it delivers access to numberless first-class adventures. For art lovers, a visit to Red Lodge should not be complete without checking out Red Lodge Clay Center located at 123 Broadway Ave S. For some quiet moments, Pride Park is a tranquil oasis and is located right in town. Besides, the historic downtown is enticingly quaint and is a pleasure to stroll through.

Hamilton

Drone view of the bitterroot mountain range in Hamilton Montana
Drone view of the bitterroot mountain range in Hamilton Montana

Travel + Leisure identifies Hamilton, Montana among the Ten Best Small Towns In the US for Retirees. Many will agree that a retirement mirrors a vacation in more ways than one. It is the period of life that one finally gets the time to be up and close to beauty in all its subtle facades. Nestled in the heart of the Bitterroot Valley along US Highway 93, Hamilton is home to just about 5,300 residents. The town is set in the backdrop of stunningly gorgeous scenery, complete with wide-open spaces and an inviting atmosphere. A first-time visit should include a detour to the Ravalli County Museum, which, for the building alone (a 1900 county courthouse) — is a treasure worth exploring. Besides, the colorful orchards that often bloom in the surrounding valley are always a sight to behold.

West Yellowstone

Sunny street view of the West Yellowstone town, via Kit Leong / Shutterstock.com
Sunny street view of the West Yellowstone town, via Kit Leong / Shutterstock.com

West Yellowstone is a rocky mountain enclave that is located in  Montana’s southwest Gallatin County. This cute, little town is home to just about 1,000 residents. Situated right at the doorpost of Yellowstone National Park’s western entrance, West Yellowstone is by far the most popular access point to Yellowstone National Park. Since the park’s entrance is not more than a mile away, Yellowstone National Park, the only place in the U.S. where bison have lived continuously since prehistoric times, is often the town’s greatest draw. But for some discovery outside the world-famous park, Hebgen Lake is an uncrowded still-water marvel located just about 12 miles from town. For some splashing, boating, or plain-old fishing, surrounded by post-card views on all sides, Hebgen Lake is worth lacing up for.

Livingston

Historic centre of Livingston near Yellowstone National Park, via Nick Fox / Shutterstock.com
Historic centre of Livingston near Yellowstone National Park, via Nick Fox / Shutterstock.com

Originally called Clark’s City, before being renamed for a railroad executive, Livingston is nestled at the edge of the Yellowstone River, the longest free-flowing river in the contiguous United States. This quaint town is the seat of south-cental Montana’s Park County. Boasting a population of about 9,000, Livingston was founded in 1882 and once served as the gateway to Yellowstone National Park. With a downtown lined with beautiful 19th-century red-brick buildings and a skyscape that features spectacular views of Livingston Peak, first-time visitors will be hard-pressed to decide between exploring the gems within the town and venturing out for some of nature’s most breathtaking views. But that said, no avid hiker ever visits Livingston without checking out Pine Creek Falls. For some of nature’s best scenery, Paradise Valley must just be on the bucket list.

Ennis

 Main Street in Ennis. Ennis is a town in Madison County, Montana, United States, in the southwestern part of the state, via Pecold / Shutterstock.com
 Main Street in Ennis. Ennis is a town in Madison County, Montana, United States, in the southwestern part of the state, via Pecold / Shutterstock.com

One may be tempted to dismiss a town with only about 1,000 residents.  However, regarded by many as Montana’s fly-fishing mecca, Ennis might be short on residents, perhaps delightfully so, but it is not short on fun-filled adventures. It might be enough to know that Ennis’s main street crosses Madison River, arguably the most famous fly-fishing river in Montana, and the gold standard by which all other western rivers must measure up to. Besides the many taverns and saloons that line Ennis’s main street, and the town’s endearing Old West look, complete with many wooden buildings that speak to its history, one may want to venture about 16 miles north to Norris Hot Springs, a popular spot for those either craving a refreshing dip or a delicious bite.

Philipsburg

Aerial view of Broadway Street of Philipsburg, Montana
Aerial view of Broadway Street of Philipsburg, Montana

Philipsburg is a not-to-miss gem that is nestled along Highway-1 in west-central Montana’s Granite County. About 900 residents call Philipsburg home and enjoy the picturesque backdrop of its Pintler Wilderness Area. Located in the heart of Montana sapphire country, a visit to Pittsburg should include an exploration of the nearby gemstone mines. A particular not-miss is the Gem Mountain whose mine is on Highway 38, a few miles off the Pintler Scenic Route. First-time visitors to this mine enjoy the hands-on thrill of finding their own Montana sapphires and subsequently processing them into custom jewelry. Besides, this property is great for those who will want to pick some beautiful gemstones on the go. For accommodation, Travel + Lesure has named The Ranch at Rock Creek the best resort in Montana.

Virginia City

Virginia City from a nearby hillside
Virginia City from a nearby hillside

With a population of about 230, one can miss Montana’s Virginia City in a blip. But that would be ironic because Virginia City was once the busiest city in Montana and served as the state’s territorial capital before yielding that honor to Helena. What spurred Virginia City to nationwide fame was the discovery of gold in Alder Gulch. While estimates vary, Alder Gulch may have held—and produced gold—to the tune of between $ 50 million and $150 million. Needless to say, it was the site of the richest gold strike in the Rocky Mountains. Virginia City would rapidly bloom on the wings of the ensuing gold rush. Yet gold would soon play out, and Virginia City nearly turn into a ghost town. Today, however, frozen in time, Virginia City is among the best-preserved gold rush towns in the American West complete with copious reminders.

Anaconda

A welcoming signboard at the entry point of the preserve park, via Cheri Alguire / Shutterstock.com
A welcoming signboard at the entry point of the preserve park, via Cheri Alguire / Shutterstock.com

The county seat of Deer Lodge County, Anaconda boasts a population of about 10,000 and is regarded as the gateway to the Anaconda-Pintler Wilderness Area. This immediately puts it on the radar of an avid outdoor enthusiast. Straddling the Continental Divide, the Anaconda-Pintler Wilderness Area is a 158,656-acre wonder defined by spectacular mountain scenery and glacially-formed geological marvels. Just about six miles from Anaconda, outdoor lovers will want to check out Lost Creek State Park, home to impressive limestone cliffs and deep-toned geologic marvels that rise more than 1,000 feet above the canyon floor. Besides, the town boasts a downtown that is lined with several entertainment and dining options. For some whistle-wetting, Club Moderne is just as great a bar—as it is a piece of history.

Stevensville

Historic St. Mary's Mission in Stevensville, Montana
Historic St. Mary's Mission in Stevensville, Montana

Encircled by the Bitterroot Mountains, a subrange of the Rocky Mountains that runs along the border of Montana and Idaho —and Saphire Mountains— named for the valuable stones predominant in its precincts, Stevensville is framed by natural grandeur on every side. Stevensville boasts a population of about 2,200 and offers first-time visitors a little bit of everything. History lovers will be delighted to learn that Stevensville is regarded as the first permanent settlement in Montana. The town's many historic buildings include the St. Mary's Mission, the first church in Montana and the first non-indigenous settlement. Stevensville also boasts several art galleries including River’s Mist Gallery and Gifts located at 313 Main Street. While the town’s nightlife scene is nothing a party hopper will rave about, the nearby Lee Metcalf National Wildlife Refuge is a birder’s dream.

Fort Benton

Historic Fort Benton, and Fort Benton Bridge, Montana, via Joseph Sohm / Shutterstock.com
Historic Fort Benton, and Fort Benton Bridge, Montana, via Joseph Sohm / Shutterstock.com

Home to about 1,000 residents, the “birthplace of Montana,” as Fort Benton is known, offers the small-town allure and historic charm that positions it among Montana’s finest small towns. Tracing its origins to the glory days of American fur trading, today, visitors to Fort Benton will confront a town whose character has undergone a complete makeover. Where scandal, violence and riot once marked everyday life, peace and calm now reign supreme. History buffs will want to check out the Old Fort Benton Bridge, the first bridge to loop across the Missouri River. Alternatively, one will want to visit the Shep Memorial and learn the fascinating story of what was once the world's most loyal sheepdog.

The Takeaway

The 41st state to join the Union may be known for its rugged mountains, high plains, and breathtaking bluffs— more than its charming small towns that are just as varied. However, that is not to say that Montana does not have a number of cute, little towns that will make first-time visitors want to linger around savoring what these beautiful towns have to offer. From Whitefish, the gateway to Glacier National Park, to West Yellowstone, the gateway to Yellowstone National Park, and many towns in between, Montana’s small towns are captivating secrets all worth discovering.

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