May is one of the best times to hit the open road in Southeast Montana. Spring sunshine, blooming prairie landscapes, and wide-open highways make the perfect backdrop for two meaningful weekends: Mother’s Day and Memorial Day.

Whether you’re planning a relaxing getaway to celebrate Mom or looking to kick off summer with an unforgettable holiday weekend adventure, Southeast Montana offers scenic drives, charming small towns, outdoor escapes, and places where memories are made.

This May, make the most of both holiday weekends with two perfect Southeast Montana Road trips.

Mother’s Day Weekend: A Scenic Escape She’ll Always Remember

This Mother’s Day, slow things down and enjoy a road trip built around connection, scenery, and time together. Starting in Miles City, the journey west toward Glendive offers quiet roads and beautiful spring landscapes along the Yellowstone River.

Start in Miles City

Begin your weekend in Miles City with a relaxed morning downtown. Grab brunch, browse local shops, and enjoy the charm of this classic Eastern Montana town before hitting the road.

Stop: Pirogue Island State ParK

Just minutes from downtown Miles City, take a peaceful detour to Pirogue Island State Park.

This 269-acre undeveloped island park sits along the Yellowstone River and offers:

• Quiet walking paths
• Birdwatching opportunities
• River views surrounded by cottonwoods and prairie

It’s the perfect slow-paced stop to stretch your legs and enjoy the quiet beauty of spring in Southeast Montana.

Optional Stop: Terry, Montana

Continue west with a short stop in Terry, a small prairie town known for its welcoming community and proximity to Makoshika’s changing landscape.

Grab a coffee, explore the local streets, and enjoy a glimpse of small-town Montana life.

Scenic Drive to Makoshika State Park

From Miles City, the drive to Glendive and Makoshika State Park takes approximately 1 hour 30 minutes to 1 hour 45 minutes (about 100 miles) depending on stops.

As you approach Glendive, the rolling prairie begins to shift into dramatic badlands formations—an unforgettable transition into Montana’s largest state park.

Explore Makoshika State Park

Spend the afternoon exploring Makoshika’s unique landscape of sandstone formations, fossil beds, and scenic overlooks. Spring is an ideal time to visit, with comfortable temperatures and fewer crowds.

Take a short hike, stop at viewpoints, and enjoy the quiet beauty of the badlands.

Stay the Night

Wrap up the day with an overnight stay in Glendive, where cozy accommodations and quiet evenings make for the perfect end to a Mother’s Day adventure.

With scenic drives, thoughtful stops, and uninterrupted time together, this road trip is a beautiful way to celebrate Mom.

Memorial Day Weekend: Adventure, History, and the Start of Summer

When Memorial Day weekend arrives, it’s time for a road trip filled with adventure. Southeast Montana is the ideal place to welcome summer—with uncrowded roads, historic landmarks, and outdoor experiences that bring the season to life.

Begin in Southeast Montana’s Historic Heart

Begin your weekend in Billings, Montana’s largest city and a great launch point for nearby attractions. Explore downtown’s local restaurants, breweries, and shops, or stroll through the historic districts before heading out.

Stop: Pompeys Pillar National Monument

Head east of Billings to Pompeys Pillar National Monument, one of the most significant historical sites in the region.

Here you can:

• See William Clark’s signature carved into the sandstone
• Walk interpretive trails along the Yellowstone River
• Learn about the Lewis and Clark Expedition

Stop: Pictograph Cave State Park

Continue back toward Billings to Pictograph Cave State Park, home to ancient rock art dating back thousands of years.

The short loop trail offers a powerful look into early human history in the region.

Stop: Hardin, Montana

Travel east along I-90 to Hardin, a gateway community near several important cultural and historic sites.

This is a great place to take a break, grab lunch, and experience a classic small Montana town.

Stop: Little Bighorn Battlefield National Monument

Just outside Hardin, explore Little Bighorn Battlefield National Monument, one of the most significant historic sites in the United States.

This solemn and powerful landscape tells the story of the 1876 battle between the U.S. Army’s 7th Cavalry and Lakota, Northern Cheyenne, and Arapaho warriors. Visitors can:

• Drive the battlefield tour road
• Visit memorials and interpretive exhibits
• Walk the scenic hills overlooking the Little Bighorn River

It’s a place of reflection, perspective, and deep historical importance.

Stop: Custer Battlefield Trading Post & Café (“Putt’s”)

After touring Little Bighorn Battlefield National Monument, continue your experience in the heart of Crow Country at the Custer Battlefield Trading Post & Café or as the locals call it, “Putt’s.”

This is a must-stop for both food and culture.

Order the standout Buffalo Burger, made with 100% buffalo meat, grilled and served with classic toppings. Pair it with the sweet potato waffle fries, a local favorite that’s worth the stop on its own.

While you’re there, browse the attached trading post featuring Native American-made goods, or take a moment to appreciate the café interior, filled with colorful beadwork and Native art that reflects the region’s cultural heritage.

Continue Your Journey Through Southeast Montana

From here, travelers can continue exploring nearby Crow Country, return toward Billings, or extend the road trip deeper into Southeast Montana’s wide-open landscapes.

Two Weekends, One Incredible Destination

This May, you don’t have to choose between rest and adventure, you can have both.

Celebrate Mother’s Day with peaceful drives, scenic beauty, and time together. Then return for Memorial Day to embrace the outdoors, explore Montana history, and welcome summer on the open road.

From springtime prairie views to unforgettable nights under the stars, Southeast Montana is made for May Road trips.

So, fill the tank, plan your route, and discover why two weekends in Southeast Montana can create a month of lasting memories at SoutheastMontana.com/Plan-Your-Trip.