Main Street in Livingston, Montana. Image credit: Nick Fox / Shutterstock.com.

6 Best Downtowns In Montana

For decades, travelers have come to Montana for drives like the Beartooth Highway, the peaks around Whitefish, and the kind of wide valley views that make the state feel almost limitless. More recently, they’ve also started building itineraries around downtown districts like Helena’s Last Chance Gulch and Livingston’s railroad-era blocks, where Montana history is packed into a few walkable streets. Boasting buildings that are forever connected to the prospectors, railroad workers, and immigrants who were lured here for work and the promise of a better life, these towns all feature walkable downtowns where you can ditch the car and enjoy exploring Montana’s less-wild side. For example, in Helena, stunning Victorian architecture housing local businesses is fun to explore, while Livingston's downtown is extremely photogenic, with a gorgeous mountain backdrop. Put these six towns all together, and you’ve got the perfect road trip across a state that truly embraces its “Big Sky Country” nickname.

Helena

A vibrant street view of Helena, Montana
A vibrant street view of Helena, Montana. Image credit: Photo Spirit / Shutterstock.com.

Montana’s capital city owes its existence to a group of prospectors known as the Four Georgians who struck gold here in July 1864. Close to giving up their search after months of failure, a final, desperate attempt gave the area its name: Last Chance Gulch. Within two years, their find had produced an estimated $19 million in gold, and the original tent city had become a proper town.

By 1888, Helena was home to some 50 millionaires, a concentration of wealth that led to the construction of the extravagant Victorian architecture that still defines the downtown core. The Last Chance Gulch name lives on in Downtown Helena, part of which has been converted into a pedestrian mall. One of only a handful of car-free downtown zones in Montana, its irregularly shaped buildings follow the boundaries of original mining claims, making for a streetscape unlike any other in the state.

Urban life in downtown Helena, Montana
Urban life in downtown Helena, Montana. Image credit: Michael Gordon / Shutterstock.com.

A walk along the mall takes you past bronze statues of famous miners, a restored streetcar, a statue of a covered wagon (aka, a “bullwhacker”), and the colorful “Women’s Mural” that pays tribute to the important role of women in the state. Just off the mall, Reeder’s Alley is a row of brick and stone tenements built between 1872 and 1884 to house miners, which is neat to explore.

Other important downtown landmarks include the Cathedral of St. Helena, an attractive neo-Gothic church completed in 1924 that dominates the skyline (it’s worth seeing for its stained glass alone). The Montana State Capitol, completed in 1902 and known for its gold-rimmed dome paintings, sits just a few blocks away.

Whitefish

Main Street in Whitefish, Montana.
Main Street in Whitefish, Montana. Image credit: Pierrette Guertin / Shutterstock.com.

It was the arrival of the Great Northern Railway in 1904 that put Whitefish on the map, and the railroad’s influence is still visible throughout this must-visit town. Railroad-related landmarks include the 1927 Tudor Revival-style train depot at the north end of Central Avenue. It’s still used by Amtrak on its Empire Builder line, making Whitefish one of only a handful of small Montana towns where you can still come and go by train.

Downtown Whitefish is undoubtedly one of the most photogenic town centers in the state, with a wide main street framed by historic storefronts, and the peaks of Whitefish Mountain Resort clearly visible at the end of the road. Central Avenue is the heart of the action and runs for several walkable blocks from the train depot past local institutions like the Great Northern Bar & Grill, a fixture since 1919 and in many ways the town’s unofficial gathering spot.

Local stores in Whitefish, Montana.
Local stores in Whitefish, Montana. Image credit: melissamn / Shutterstock.com.

Loula’s Cafe is another downtown staple. Set in the lower level of the town’s old Masonic Temple, its lemon-stuffed French toast and homemade pies are to die for. Both get even busier during the Whitefish Winter Carnival, held in February with downtown parades, snow sculptures, and the Penguin Plunge into Whitefish Lake.

Livingston

Main Street in Livingston, Montana
Main Street in Livingston, Montana. Image credit: Photo Spirit / Shutterstock.com.

When the Northern Pacific Railroad reached Livingston in 1882, it transformed what was then a simple frontier settlement into the original gateway to Yellowstone National Park (the Yellowstone River passes right through town). Within 20 years, the railroad added the Livingston Depot Center, an elegant Italianate train station that continues to welcome tourists in its role as a museum dedicated to railroad history.

Across the street, the Murray Hotel was built in 1904 to accommodate those first rail passengers and has preserved its rare original 1905 hand-cranked elevator, and is a great place to stay while exploring Downtown Livingston. In fact, none other than the late Anthony Bourdain listed it among his top 10 favorite hotels in the world and included it in his hit show, No Reservations.

Park Street, Livingston’s main drag, is fun to wander, especially during the Livingston Roundup Rodeo. Things do get busy, though, as the event attracts hordes of professional cowboys and round-up fans from across the country, so plan as far ahead as you can.

Red Lodge

The beautiful Main Street of Red Lodge, Montana
The beautiful Main Street of Red Lodge, Montana. Image credit: melissamn / Shutterstock.com.

Red Lodge can trace its roots back to 1887 with the opening of the area’s first coal mine. In just a few short years, hundreds of immigrants from across Europe turned up to work the mines, causing the town’s population to swell to around 6,000 souls at its peak in 1915 - a far cry from its present-day population of 2,500.

Between 1895 and the closing of the last coal mine in 19936, commercial buildings sprang up in ever-increasing numbers along Broadway Avenue. Fortunately for Red Lodge, this devastating loss was offset by the completion of the Beartooth Highway in 1936. One of the prettiest scenic drives in the entire country, this spectacular 68-mile National Scenic Byway climbs an incredible 10,947 feet before descending into Yellowstone and is a major tourist draw for the town.

Red Lodge’s Commercial Historic District encompasses much of the downtown core and runs along Broadway. Highlights include the Carbon County Arts Guild & Depot Gallery, located in a restored 1889 train station, and the Carbon County Historical Society Museum, which covers the town’s mining heritage and rodeo history. Also worth visiting, the Buses of Yellowstone Preservation Trust on North Broadway displays pre-war buses once used for Yellowstone tours.

Philipsburg

Local businesses in historic buildings flank the Main Street of Philipsburg, Montana.
Local businesses in historic buildings flank the Main Street of Philipsburg, Montana.

Founded in 1867 during Montana’s silver boom, Philipsburg’s fortunes were tied to the nearby Granite Mine. Though closed and now preserved as Granite Ghost Town State Park, it was once the world’s richest silver mine, producing around $40 million of the precious metal before the market crashed.

Of the 24 mining settlements that once dotted Granite County, Philipsburg is the sole survivor. Although a ghost town by the 1980s, a grassroots revival effort gradually transformed the old storefronts on Broadway Street into the colorful facades you see nowadays. One of the best, The Sweet Palace, is a Victorian-style emporium boasting countless varieties of traditional candy.

The Sapphire Gallery is another fun stop and sells bags of gravel containing precious stones mined in the nearby Sapphire Mountains. Though a 20-mile drive outside town, the Gem Mountain Sapphire Mine is still active and lets you find (and keep) stones of your own.

Other downtown attractions include the Granite County Museum with its Ghost Town Hall of Fame exhibit, the Montana Law Enforcement Museum with its preserved prison cells, and the Philipsburg Theatre. Established in 1891, it’s the oldest continually operating theatre in Montana and still hosts live performances.

Lewistown

Main Street in Lewiston, Montana
Main Street in Lewiston, Montana. Image credit: Jesse Shapins via Flickr.com.

Located at the geographic center of Montana, Lewistown originated as a supply hub for gold miners and ranchers in the late 1800s. Streets here run in a tight grid, with shorter-than-usual blocks that were designed for horse traffic in the 1880s. The buildings themselves are notable for their high-quality stonework, done by Croatian stonemasons who left their mark on structures throughout downtown Lewiston.

A fun downtown walk here includes the ornate Fergus County Courthouse, completed in 1908 and the focal point of the town’s Courthouse Square District (just look for its unique clock dome tower). The Silk Stocking District is another interesting place for a stroll. Named for the wealthy residents who could afford silk stockings at a time when most other townsfolk couldn’t, seven large residences built between 1904 and 1919 dominate the neighborhood.

Back on Main Street, the Mint Bar and Grill carries a name once common to Montana bars. During the Gold Rush era, saloons adopted the "Mint" branding to entice railroad workers to spend their hard-won cash. The 406 Cafe, regularly voted Lewistown’s best restaurant, is where you go for a hearty breakfast or lunch and boasts a classic American diner vibe.

Six Downtowns Under One Big Sky

Boasting walkable downtowns and original historic architecture, Montana's small towns offer a genuine Old West charm hard to find elsewhere. From former railroad hubs to old mining camps that once marked the edge of the Old West’s frontier, Montana’s best downtowns are perfect getaways for those willing to slow down long enough to get to know them.

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