Mainstreet in Whitefish, Montana. Editorial credit: Beeldtype / Shutterstock.com

6 Picturesque Towns In Montana For A Weekend Retreat In 2024

While Montana is best known for Yellowstone National Park, it’s also home to nine National Park Service areas that showcase the state's natural beauty, attracting millions of visitors each year. Around these natural wonders lie a variety of small, spirited towns, ranging from resort destinations to historic communities. Ready to escape for an unforgettable weekend but don’t know where to begin? Each of these six towns promises a short but sweet escape into the history and nature that makes Montana so special.

Livingston

Historic centre of Livingston near Yellowstone National Park
Historic centre of Livingston near Yellowstone National Park. Editorial credit: Nick Fox / Shutterstock.com

Sitting along the Yellowstone River, with towering mountains as its backdrop, the town of Livingston feels like a scene straight out of a Western film. The nearby river offers plenty of adventure sports to enjoy during a weekend trip, including whitewater rafting, chartered raft trips, and kayaking. Travelers can also explore the Absaroka Mountains on horseback, following trails that wind through the lush Gallatin National Forest. Within the town, a number of restaurants offer local cuisine options rooted in Montana’s culture, such as The Mint Bar & Grill, which serves delicious burgers, steaks, and craft beer, and The Outpost, which serves hand-tossed pizzas that visitors can enjoy on a scenic terrace. Just a short drive away, visitors can stay at the rustic, family-owned Antler Lodge, a log-cabin-style retreat that embodies the essence of Montana.

Dillon

Dillon, Montana
Downtown Dillon with store fronts and courthouse in Dillon, Montana. Editorial credit: Charles Knowles / Shutterstock.com.

With a population of just over 4,000 residents, Dillon may seem like an unassuming town at first glance. However, it is full of unique activities and events that encompass the Montana culture. Travelers looking for an out-of-the-norm experience can visit one of the nearby ghost towns, one of which is in Bannack State Park. Once established as a prosperous mining town in the late 19th century, the gold mines dwindled over the decades until the town was practically empty in the 1950s. As a result, visitors can visit the area today, exploring around 60 structures that remain standing. Fly fishing is a popular activity in the area as well, and visitors can enjoy it at either the Beaverhead or Big Hole River. Dillon also has a number of memorable events that happen throughout the year, such as the annual Fall Fest, which takes place the Saturday before Halloween, and its holiday Parade of Lights and Christmas Stroll event, happening in December and featuring hot chocolate, caroling, gift wrapping, and more. Angler Village Inn is a quaint lodging choice with rustic-style rooms, a wine lounge, and an espresso bar for its guests to enjoy!

Hamilton

Drone view of the Bitterroot Mountain Range in Hamilton, Montana
Drone view of the Bitterroot Mountain Range in Hamilton, Montana.

Hamilton is rich in agriculture, being a central trading hub for many small ranches, farms, and orchards around the valley. A great way to experience this agricultural community firsthand is by visiting the Hamilton Farmers Market, taking place from May through October every Saturday morning and selling all kinds of products, including fresh jams, vegetables, flowers, and crafts. A lot of the town’s history has also been preserved in the Daly Mansion, a Georgian-Revival style home dating back to the 19th century, with 50 rooms, 25 bedrooms, and 15 bathrooms. The nearby Bitterroot National Forest is a unique outdoor adventure as well, with sections in both the Bitterroot Mountains and Saphire Mountains and home to impressive wildlife species such as the moose, elk, bear, big horn sheep, rocky mountain goat, and more. Hamilton has an abundance of nature-centered lodging options, many sitting on the foothills of the mountains. Angler’s Lodge & Cabins is just one example: sitting along the bank of a lake and looking out towards the Bitterroot mountains.

Big Sky

 Big Sky, Montana
The beautiful town of Big Sky, Montana. Editorial credit: Zorro Stock Images / Shutterstock.com

With a population of fewer than 3,000, Big Sky still offers a wealth of recreational opportunities, from wild white waters and wilderness hikes to trout-filled streams and fields of wildflowers. The Big Sky Community Organization maintains 36 miles of public mountain trails, offering options for hiking, biking, and skiing. The Custer Gallatin National Forest is also an excellent option for spending a Saturday. It features a pine savannah ecosystem and impressive geological features such as steep buttes. For those curious about the area’s ranching history, the Crail Ranch Museum features some of the town’s oldest log buildings, once an active ranching operation that extended some 960 acres. Are you in need of accommodation for the weekend? The town has plenty of cozy lodges to choose from, one excellent option being the Huntley Lodge, a slope-side ski lodge with direct access to the surrounding mountain activities.

Fort Benton

Aerial view of Fort Benton, Montana
Aerial view of Fort Benton, Montana. Editorial credit: Joseph Sohm / Shutterstock.com

Fort Benton, known as the "Birthplace of Montana," boomed during the gold rush in 1862. Today, visitors can explore centuries of history at Fort Benton's many landmarks, including the prominent Old Fort Benton. This site showcases period furnishings, a blacksmith shop, a fur trade warehouse, and more. To further learn about this area’s peoples, visitors can stop by the Museum of the Northern Great Plains, which exhibits the lives of the very fur traders, cowboys, and pioneers who once resided on the land. Those up for an expedition can also travel along Old Forts Trail, which the US Calvary and Traders used over a century ago. In addition to its history, this route also passes through beautiful natural areas, such as the Missouri River, mountains, and valleys carved during prehistoric times. The Grand Union Hotel makes a great lodging choice for the weekend, built back in 1882 during one of Fort Benton’s most prosperous eras. Today, the rooms are elegantly furnished to reflect its history, with many having views that overlook the Missouri River.

Whitefish

Whitefish, Montana
The charming downtown area of Whitefish, Montana. Editorial credit: Pierrette Guertin / Shutterstock.com

Whitefish’s landscape is post-card worthy, bordering Glacier National Park and lying in the Northern Rocky Mountains. There are plenty of adventure activities to take part in during a weekend away, such as hot air ballooning over the green flathead valley or sledding down one of White Fish Mountain Resort’s alpine slides. For those looking to fully immerse themselves in nature, Glacier National Park offers over 700 miles of trails to choose from, many winding through carved valleys, alpine meadows, and lakes. Camas Road within the park is a scenic option for bikers, with mountains framing the path in the distance. After a day filled with outdoor recreation, travelers can grab a bite at one of the town’s impressive restaurants, such as Herb & Omni, which serves a sophisticated and modern menu using ingredients that come from nearby farms and ranches. To end the day, Grouse Mountain Lodge is an excellent spot to unwind, located next to the Glacier Nordic Center and Whitefish Lake Golf Course. The lodge offers amenities such as a swimming pool, restaurant, coffee bar, spa, and more.

Final Thoughts

While visitors could easily spend a week or more exploring these towns and their surrounding natural, historical, and recreational attractions, the activities outlined above provide a great starting point, especially for those with limited time. Additionally, choosing an authentic local lodge or hotel enhances the experience, allowing travelers to immerse themselves more fully during their short getaway. Whether you want to dive into Montana's history, experience its culture, or explore its stunning nature, one of these towns is sure to cater to every traveler’s preference.

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