Guest blog and images by Cayleigh & David Barbeau / Made to Explore

Welcome to Southeast Montana’s wild and wondrous landscape, where adventure and natural beauty meet small-town hospitality. Nestled in the heart of big sky country, this enchanting region boasts a rich blend of history, open roads, and outdoor splendor.

From the rolling plains of Billings to the towering cliffs of Makoshika State Park, Southeast Montana offers a variety of terrain to be explored. With fewer crowds, a ton of accessible public land, and a slower pace of life, you’ll have the opportunity to truly connect with nature and experience the magic of the Montana wilderness.

Scattered throughout this region are several vibrant small towns that serve as gateways to the great outdoors. We experienced a warm welcome and genuine hospitality everywhere we went, whether we were dining at a local eatery or venturing out on a new trail.

If you’re an outdoor enthusiast, a wild camper, or are simply looking to explore vast, untouched wilderness this winter, there is nowhere better than Southeast Montana.

"Nowhere better to get some perspective. Nowhere better to find some space. Nowhere better to hit the open road."

In this blog post, we will cover everything we loved about visiting Southeast Montana this winter. We hope this itinerary inspires you to get lost in the rolling plains, rugged badlands, and lush river valleys of this beautiful region.

Miles City

Our journey began in the historic town of Miles City. We arrived famished from our drive, so we stopped at Tilt Würks Brewhouse & Casino, a cozy eatery serving delicious comfort food and local brews. The staff was wonderful and our meals were fantastic. We would highly recommend the Spicy Buckin’ Bronco Burger!

This is one of over 20 restaurants on the Southeast Montana Burger Trail. These one-of-a-kind burgers have been hand-picked and laid out in a convenient route allowing visitors to refuel and get an authentic taste of Montana. Make sure to download the free Burger Trail Passport where you can check into different locations to win prizes.

After lunch, we made our way to the WaterWorks Art Museum. Housed in a beautifully restored historic building, this museum showcases the talent of local and regional artists. Each display provides valuable insight into the cultural landscape of Southeast Montana.The lovely lady at the front was incredibly passionate about both the museum and Miles City, sharing loads of interesting information with us.

Fun fact: This museum is located in the cisterns of the old water treatment plant and they change the exhibitions monthly.

Other things to do in Miles City include a stroll downtown to admire the historic buildings, a wine tasting at the Tongue River Winery, or a few hours shopping for antiques at Vintage And Rustics.

Strawberry Hill

Next, we made our way to Strawberry Hill for a sunset hike. Only 10 minutes from Miles City, this area is a haven for outdoor lovers. One of the most popular routes is the Strawberry Hill Loop, a picturesque hiking trail that winds through rugged terrain with breathtaking views from the top.

In total, this hike is 5.6 kilometres(3.5 miles) + 130 metres(425 feet) of elevation gain. We would highly recommend lacing up your hiking boots and making it to the peak for sunset. The colours in the sky are phenomenal!

After our hike, we cooked dinner in the van and stayed the night at the trailhead. Because Strawberry Hill is located on BLM(Bureau of Land Management) Land, visitors are allowed to wild camp. We LOVE that adventurers can pitch their tents or park their vans here. It’s the perfect place to immerse yourself in the tranquility of nature under the starry sky.

IMPORTANT: This privilege comes with great responsibility and campers are reminded to practice Leave No Trace principles. By packing out all trash, minimizing campfire impacts, and respecting wildlife and other visitors, we can ensure that future generations get to enjoy these areas for years to come.

In the morning, we woke up and went for a cross-country ski along Strawberry Hill Road. The views were pristine and there wasn’t another soul in sight. There are no track set areas at Strawberry Hill. If you enjoy creating your own path, though, you will love it here!

Terry Badlands

From Strawberry Hill, we drove about 40 minutes east to The Terry Badlands. This is another BLM area where you can camp, hike, hunt, and immerse yourself in nature. The Terry Badlands are home to otherwordly beauty including colourful, banded cliffs that overlook the surrounding prairie. 

“Geologic features include sandstone bridges, spires, table tops, and buttes divided by many deep gullies all formed by thousands of years of wind and water erosion.”

The US Department of the Interior BLM website

A few noteworthy hikes in the area include the Castle Rock Loop, Calypso Trail, and Natural Bridges Trail. Instead of hiking, we decided to hop on our fat bikes and ride along Scenic View Road. This is an excellent option if you don’t have a 4X4 vehicle or if the roads are wet/snow-covered when you visit.

If you’re hungry after your adventure, the town of Terry is home to another Burger Trail restaurant called Roy Rogers Bar Grill & Casino. Make sure to try the Fried Green Tomato & Bacon Burger.

Makoshika State Park

Finally, we drove 45 minutes to Makoshika State Park, which is a treasure trove of natural wonders. We began at the visitor center, where we browsed fascinating exhibits showcasing the park’s rich geological history and remarkable dinosaur fossils.

Next, we put on our crampons, grabbed our hiking poles and started exploring. This entire park is full of winding trails and scenic viewpoints, but one of our favourites was the Twin Sister Viewpoint via the Switchback Trail. In total, this hike is 2.9 kilometres (1.8 miles) + around 100 metres (328 feet) of elevation gain.

It was extremely peaceful and we enjoyed seeing all the different rock formations along the trail. We arrived at the top for sunset which completely blew us away. Make sure to bring a headlamp for the hike down!If you are travelling in a van or an RV, Makoshika offers a fantastic campground nestled amidst the rolling hills and towering buttes. Here, we slept beneath the star-studded sky and enjoyed the stillness of nature. Sidenote: Makoshika is an exceptional place for stargazing!

In the morning, we savoured a cross-country ski around the campground before heading off to our next adventure. Another great activity in Makoshika is the scenic disc golf course that winds through the state park.