If you’re planning a summer vacation to Yellowstone, remember that half the fun is getting there. Instead of driving right to Yellowstone, we encourage you to get off the interstate to dine, drink, and discover all the fun things to do in southeast Montana.

Things To Do On The Way To Yellowstone National Park

This guide brings you from North Dakota into Southeast Montana. We suggest adding time to explore Medora if you come from this direction.

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Visit Southeast Montana provided some of our activities and lodging.

Bismarck and Medora, North Dakota

We “started” our southeast Montana vacation in Bismarck, ND. We also decided to explore this region because Bismarck is a 7-hour drive from Mankato, MN. Check out the vegan options we found in Bismarck.

Which Route is Best?

If you’re planning a summer vacation, we recommend a big loop to take in as many things as possible, as there are so many things to do on your way to Yellowstone National Park.

This route gives you the best of both worlds. The Badlands National Park in South Dakota on I-90 is an excellent vacation. We suggest not missing the underrated Theodore Roosevelt National Park. With all the things to do in Southeast Montana, your vacation will be fun!

This article focuses on everything to do on the way to Yellowstone, so our trip took us on I-94 and home on I-90.

Road Tripping From the East?

From Bismarck, consider a night or two in Medora, ND. Medora is another western town that should not be missed, and it is the entrance to Theodore Roosevelt National Park South Unit. TRNP is underrated, and you will undoubtedly notice the difference in travelers if you visit both the Badlands and TRNP.

We’d previously been to the South Unit and added the North Unit to our itinerary for this trip. Read about all the reasons you should head to Medora, ND. We found vegan options in Medora as well! Click for additional hotel options in Medora.

Things to do In Southeast Montana

We found so many things to do along the way in southeast Montana. This area should not be overlooked or passed through on your way to Yellowstone, as there are many things to do!

Here are some ideas for fun ways to get out and stretch your legs on the way to Yellowstone. We’ll share some stops you can make for things to do on the way to Yellowstone and hotels to spend the night going through southeast Montana.

Day 1: Explore Glendive, Montana

Glendive is 110 miles NW of Medora, ND, and checks our motto’s boxes to dine, drink, and discover.

Medora, ND, to Glendive, MT, is 58 miles. Glendive is the cutest town, and we found plenty to do here.

Where to stay in Glendive, MT: Holiday Inn Express. This hotel was nice and clean. We enjoyed the small kitchen area in our room so we could prepare road trip food!

Glendive is home to Montana’s largest State Park, Makoshika State Park. This park is over 11,500 acres. This state park is known for dinosaur fossil remains. The park offers dinosaur digs and other group events like hiking and stargazing.

Visitors can drive through Makoshika State Park for scenic overlooks and access to hiking, biking trails, and camping.

Consider spending several hours or more depending on what activities you plan to do while you’re here.

Murals are popping up in Glendive, and we had fun driving through town to find them. They also have sculptures scattered throughout the town. They are cute and nostalgic.

The Historic Bell Bridge is a great stop to make. The Bell Street Bridge is on the National Register of Historic Places. Today, the bridge serves as a pedestrian & bike bridge that is 1/4 mile across.

Pro Tip: Head to the Historic Bell Bridge to see it lit at night!

Due to the 4th of July holiday weekend, we only ate one meal in Glendive. There are more options if you’re not looking for vegan options like ours. We had a great Mexican lunch at Los Amigos Mexican Restaurant. The food was great, the portions were huge, and the service was excellent.

We love to find local breweries wherever we go. Glendive, MT, has one brewery, Cross Country Brewing, and they have a great patio.

Day 2 Finish Glendive, then Drive to Circle, MT

Circle, MT, is 49 miles NW of Glendive. For the Working Horse Ranch experience, plan to spend most of your day at the ranch.

Sleep at a Working Horse & Cattle Ranch in Circle, MT

For an authentic Western experience, we recommend booking a night (or more) at the Mahlstedt Ranch. This will be an unforgettable ranch experience.

This is a working horse and cattle ranch that offers an Airbnb. Customize your stay at the ranch with numerous activities. Read more about our fantastic experience here.

This will be an experience of a lifetime that you can have and is one of the top things to do on the way to Yellowstone.

Day 3 Miles City, MT

Miles City is 96 miles southeast of Circle, MT, on I-90

After you have spent the morning saying goodbye to the ranch, make your way to Miles City, MT.

Stop for a giant bloody mary and appetizer at Black Iron Rotisserie. 

Visit the Range Riders Museum. Plan for several hours at this stop, as the museum has over 38,000 square feet of historical collections celebrating Montana’s history. 

You don’t have to be a history buff to appreciate the collections at Range Riders Museum. A stop here will tie in historical events with other things to do on the way to Yellowstone.

This museum was founded in 1939 by a group of cowboy stockmen at the site of Fort Keogh, which is tied to the Custer Battle. Enjoy dioramas, gun collections, Native American artifacts, cowboy boots, cowboy hat collections, and more.

Go to Tongue River Winery to taste local wines. They only use grapes that can be grown in Montana. They are also Harvest Hosts, and we met several people camping at this winery during our visit. 

Head to any of the local shops that are located right next to the Historic Montana Theater. Vintage and Rustics in Montana and Girl Ran Away With The Spoon have cute things! Grab a Montana Gift at BuyMT before hitting the road. 

Where to stay in Miles City: Sleep above the Historic Montana Theater. Grab some takeout and relax in the living room for dinner. This Airbnb, which is a movie-themed apartment, has been historically restored. It even comes with complimentary tickets to a movie downstairs!

Billings, MT

Miles City to Billings is 145 miles southeast on I-94.

Billings, MT, surprised us! We recommend spending several nights here to take in what Billings offers. There are plenty of things to do on your way to Yellowstone in Billings alone. 

There are so many things to do in Billings that we couldn’t fit it all in, and we stayed three nights! We suggest using Billings as a home base for a few days to take in all the things to do in Southeast Montana. 

Tour Moss Mansion Museum

The Moss Mansion is an excellent stop. This historic home was built as a private home in 1903 and is incredibly opulent. We highly recommend a tour. Plan for 1-2 hours. There is so much detail inside and outside of the mansion. 

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Explore The Rimrocks in Billings

The Rims are located near Billings-Logan Airport; Swords Park is a natural park in Billings that is over 60 acres. It’s great for a walk and has fantastic views of Billings. 

This is such a very cool geological feature right within city limits. You can stop at various places along the Rim and hike around the area. It’s a must-see if you’re looking for outdoor things to do in Billings.

Dine & Drink in Billings

We’ve mentioned this before, but we love visiting local wineries and breweries when we travel. We recommend the Billings Brew Trail, which takes you on a 1.5-mile loop in downtown Billings.  We only had time to visit one brewery during our stay as we were too busy taking in all the sites.

The Billings Brew Trail comprises nine breweries, three distilleries, a cider mill, and a winery. Talk about a good time! The best part is it’s all walkable.

Billings has a great food scene. We found some great vegan meals. Read our guide to the best vegan options in Billings and southeast Montana. 

Here’s a teaser- the General Tso’s at Marble Table is fantastic!

Easy Day Trips from Billings

These attractions are close to Billings, are easy day trips, and have great things to do on the way to Yellowstone. 

Pompeys Pillar National Monument

31 miles east of Billings. Take Exit 23 off of I-90. 

Pompey’s Pillar National Monument should be on your list of things to do in Southeast Montana. Use your National Park Pass for free entry. We packed a lunch and ate outside before exploring. Plan for 1-2 hours here minimum.  

Pompeys Pillar has historical significance in southeast Montana as it holds the signature of Captain William Clark. You can hike on a boardwalk with stairs to see his autograph. Climb to the top for beautiful views of the Yellowstone River.

Head to Roundup for a Rodeo and lunch

Roundup is 45 miles north of Billings

Yes, this southeast Montana town is called Roundup. This small, western town is located in the valley near the Musselshell River and the Bull Mountains.

If you happen to travel through Roundup on the 4th of July, you can attend Rodeo Roundup. According to the rodeo announcer, the rodeo is also known as Cowboy Christmas.

Between the rodeo and the 4th of July parade, it was the most wholesome, all-American experience you could imagine.

Stop in for a delicious bite at The Backporch. We didn’t expect to find a James Beard Semi-Finalist for best new restaurant in Roundup, a town of 1,800 residents in the country. Click to read about our meal at this popular BBQ spot.

Take a Guided Tour of Little Bighorn Battlefield National Monument

Little Bighorn Battlefield National Monument is 64 miles west of Billings on I-90.

You can drive through the Little Bighorn Battlefield National Monument, but let us suggest a guided tour with Rose of Indian Battle Tours. Her animated story-telling made us want to learn more about the battle here and what led up to Custer’s Last Stand.

What would have otherwise felt like a beautiful and peaceful scenic drive, the preserved battlefield is stunning and peaceful today and is enhanced with a guided tour from someone who has studied the battle for decades. We consider this one of the best things to do on the way to Yellowstone.

You can also listen to park rangers give talks with background, and the interpretive center is a great place to learn more about the Little Bighorn Battle.

Road Trip to Red Lodge from Billings

Red Lodge is 63 miles southwest of Billings.

Red Lodge is an adorable mountain town full of charm.  We stopped for breakfast at Cafe Regis before hitting the Beartooth Highway. If you’re passing through, you could easily plan to spend a few hours to a half-day in Red Lodge. Here are other things to do in Red Lodge.

Beartooth Highway

Beartooth Highway is one of the most beautiful scenic drives in America. This is one of the most amazing things you can do on the way to Yellowstone.  It’s an unforgettable experience. This highway has the highest elevation of the Northern Rockies, so the best months to visit are July-early September. Snowfall will close the roads throughout the rest of the year. 

To access Bearthooh Highway, go to Red Lodge and continue on US Route 212. It’s nicknamed “Highway to the Sky” for good reason. The route is 69 miles and ends at the northeastern entrance of Yellowstone National Park. 

Plan for a minimum of 2 hours to drive Beartooth Highway. We recommend taking additional time to stop for what pulls your attention. 

You can easily make a day trip from Billings to Beartooth Highway.

A Fork In the Road

You have a choice here to head right into the northeastern entrance of Yellowstone National Park or go left to get on the Chief Joseph Scenic Byway.

We want to devote a separate trip to Yellowstone, but we thought it would be a great place for lunch. Since we have our National Park Pass, it didn’t cost us anything and was a great teaser to plan that trip out to Yellowstone!

Chief Joseph Scenic Byway

Chief Joseph Scenic Byway is 92 miles from Billings. 

At the end of Beartooth Highway, you can go straight and continue to Yellowstone National Park Northeast entrance or take the Chief Joseph Scenic Byway. 

The Chief Joseph Scenic Byway is another “must” for things to do on the way to Yellowstone and is in Wyoming. 

The landscape and views are so different from Beartooth Highway. 

Should you Stay in Billings and take a Day Trip to Beartooth Highway and Chief Joseph Scenic Byway?

We did both of these drives from Billings in one day. It’s doable.

We devoted one day to these two scenic drives, but you could easily stay in Red Lodge, where many great lodging options exist. 

Where to stay in Billings: We recommend the Boothill Inn. The location is excellent; it’s spotless with great hospitality. We loved the wet bar in our room as we were able to pack road trip snacks and meals. Here are other lodging options in Billings. On our next visit, we want to stay at the Northern Hotel for a downtown vibe and to partake in the Billings Brew Trail.

Things to do on the way to Yellowstone

We’ve shown you plenty of fun things to do in southeast Montana. With this list of things to do on the way to Yellowstone, it’s worth spending a few extra days exploring all the things to do in Southeast Montana.

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