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From turn-of-the-century saloons and Lewis and Clark landmarks to quaint B&Bs and grizzly bears in Montana’s only zoo, Southeast Montana has a treasure trove of fun — and often quirky — road stop attractions. Whether you fly into Billings and rent a car or drive over state lines, here are our suggestions for 72 awesome hours in Big Sky Country.

This road trip starts in Billings, heads east towards Miles City, and then back to Billings for a final day of exploring. We’ve plotted out fun stops, restaurants to fill your belly, and hotels that offer a comfy and cozy night sleep to prepare you for the next day’s adventure. Since we've sorted out the fun, all you have to do is get there.

Photo Credit: Jade Broadus

4 Things to Know Before You Go

  1. Billings, nicknamed Montana’s Trailhead, has non-stop flights from 10 major cities in the United States.
  2. Check out the Visit Billings website for travel deals on lodging and activities to make your visit super affordable.
  3. Plan your visit with stops at one of the many state parks and national recreation areas in and around Billings.
  4. Hikers, birders, animal lovers, adventurers and families will love exploring Southeast Montana because there really is something for every type of traveler.

Photo Credit: Jade Broadus

Where to Stay

  • Billings: The Northern Hotel is located in downtown Billings within walking distance to many breweries, restaurants and shops. As a member of Preferred Hotels and Resorts, the Northern offers a modern luxury experience, complete with two restaurants on site (for breakfast and cocktails). The king bed suites have a spacious living area to spread out and relax in, too.
  • Miles City: Experience historic Montana in a newly renovated B&B. Each of the five rooms at Horton House B&B is designed based on a significant historical figures of Southeast Montana. The locally owned and operated B&B not only provides a comfortable environment to learn more about the history of Miles City and the Lewis and Clark trail, with insider knowledge and tips from the B&B’s owner, but also has cozy accommodations and a hearty, 4-course breakfast each morning.

Day One: Get to Know Billings

9am: Before you even exit the airport parking lot stop at the Yellowstone County Museum in Billings. This free museum is home to over 15,000 artifacts and mementos from the area’s history. You get a quick glimpse into the area before you set off on the road trip. The full size covered wagon display immediately puts you on the Lewis and Clark Trail and allows you to imagine what life was like traveling along the Yellowstone River with all your belongings in your one wagon. The basement room also includes two walls of Native American artifacts, including everything from beaded moccasins to weaponry. If you are traveling as a family, this is also an ideal place for you (and the kids) to stretch your legs before jumping back in the car. Don’t forget to snap a photo atop Rimrocks of the city below.

Noon: The hills around Billings are great for anyone that wants to catch a bird’s eye view of the city. Popular hiking trails include: Rimrock West, Pictograph Cave State Park, and Four Dances State Recreation Area.

4pm: The Pub Station is one of Billings many taprooms and concert halls, featuring live music many times each week. If a show isn’t on the schedule the day you’re in town, check out the arcade room for some classic arcades with one of their 34 pints on draft.

6pm: There are seven microbreweries and breweries and one distillery in the downtown Billings area that are sure to help you unwind after a long day of traveling and exploring. We recommend sampling from a few to get a taste of the unique flavors being brewed in the area.

Photo Credit: Jade Broadus

Day Two: Onward to Miles City

8am: Before embarking on the two-hour car ride to Miles City, lace up your shoes for a bike ride through Billings. You can explore one or more of the 26 miles of bike trails in the area with ease. Didn’t bring your own bike? No worries! You can borrow one from the Visitor’s Information Center at no charge. While you’re there, they’ll give you a mini tour on a city map so you can pick out the perfect trail for your ride.

Noon: Downtown Miles City isn’t very big; however, no stop through the town is complete until you’ve walked into the historic Montana Bar and chatted with the bartender. While she pours you a pint of a state-brewed beer, notice the old cash register and the original 1908 Italian tile flooring. The walls are lined with steer heads and in the window is a now extinct Audubon Big Horn Sheep. Known for being one of the best restored bars in all of Montana, don’t leave without taking a peek inside the men’s bathroom for a one-of-a-kind marble urinal and try to locate the bullet hole in the front windows from a accidental gun misfire. The atmosphere is as unique and genuine to Montana as the food offerings.

2pm: Located in a park along the Yellowstone River, the WaterWorks Art Museum is an art gallery like you’ve never seen before — the building is just as interesting as the art that lines its walls. Once used as the water holding tanks for all of Miles City (the water was pumped in from the Yellowstone River and held inside), the building is now an art gallery and living history museum.

4pm: Open year around, the Tongue River Winery has a 45-seat tasting room and a three-acre winery perfect for an afternoon tasting adventure. Once you’ve found your favorite, be sure to grab a bottle for a fun flavorful souvenir.

7pm: Tilt Würks Brewhouse and Casino is a restaurant and bar filled with vintage arcade games. Try your luck at one of the pinballs while taste-testing some local brews as a fun nightcap.

Photo Credit: Jade Broadus

Day Three: Loop Back to Billings

10am: About 25 miles east of Billings, and an ideal spot to get off I-94 and experience some of Montana’s two-land country roads, is the only living memory of the Lewis and Clark Trail: Pompeys Pillar National Monument. The interpretive center outlines the history of this area in relationship to its early settlers along with several battles and includes a replica of the famous Captain Clark signature. A newly-constructed wooden walkway is located just outside the center’s back doors, so you can climb to the top of the pillar for yourself and look out over the Yellowstone River. From there you can also spot Clark’s signature that he carved into the stone back in 1806.

Noon: Once you’ve arrived back in town, you’ll want to explore Moss Mansion, one of the oldest, and most expensive at the time, houses in Billings. Many months, there are daily, guided tours of the 1904 mansion available on the hour, where you can learn about the rich history of the area and the builder of the house in more detail. P.B. Moss and his wife moved to Billings with their six children and spent over $100,000 dollars on this home, quite a strong contrast to the nearby houses that averaged at about $5,000. The tour guides you through each of the 26 rooms, detailing what life was like in Billings at the turn of the century, and how different life looked for the wealthy living on the frontier.

2pm: Let’s be honest, seeing a grizzly bear is on everyone’s bucket list whether they admit to it or not. The huge, beautiful omnivores are a staple of Montana’s history and culture after all. ZooMontana will help you experience a grizzly in the best — and safest — way possible: close up but behind a fence.

Photo Courtesy Visit Billings

This guide is just a scratch at the surface of exploring Billings and Southeastern Montana. If you have more time or are planning your own Southeast Montana trip, download the Billings scenic guide to help in your itinerary building. Or, download the audio map app to your smart phone and get live updates as you walk or drive around the city.