The Theodore Roosevelt Presidential Library’s 2026 opening in Medora, North Dakota, is the perfect reason for a Midwest road trip. Whether you’re coming from Minnesota, South Dakota, or Montana, you can turn your drive into a memorable part of your adventure. Here’s how to plan your route, where to stop, and how to make the most of your journey, whether you’re traveling as a family or a couple.
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Why Make the Drive a Road Trip?
Distances in the Northern Plains are bigger than they look, but that just means more opportunities to explore small towns, local eats, and scenic views along the way. Instead of rushing to Medora, use these suggested routes and stops to get a real taste of the region.
Don’t forget to check out my travel must-haves HERE
Route 1: From Minnesota (Fargo or Detroit Lakes to Medora)
- Main Route: I-94 West from Fargo through Bismarck, Dickinson, and on to Medora
- Must-See Stops:
- Fargo: Downtown murals, coffee shops, family-friendly parks
- Jamestown: World’s Largest Buffalo, Frontier Village
- Bismarck: Riverfront walks, local breweries, great food
- Dickinson: Badlands Dinosaur Museum, local diners
- Medora: Gateway to the Library and Theodore Roosevelt National Park
- Family Tips: Plan playground breaks and ice cream stops; Jamestown and Bismarck are especially kid-friendly
- Couples Tips: Try a brewery in Bismarck, sunset at Painted Canyon overlook
Route 2: From South Dakota (Sioux Falls, Watertown, or Brookings to Medora)
- Main Route: I-29 North to Fargo, then I-94 West to Medora
- Alternative: US-83 North through Pierre and Bismarck to Medora
- Must-See Stops:
- Sioux Falls: Falls Park, downtown dining
- Watertown: Redlin Art Center, coffee shops
- Brookings: Children’s Museum of SD, local bakeries
- Pierre: Missouri River views, SD State Capitol (if taking US-83)
- Bismarck: (see above)
- Family Tips: Children’s Museum in Brookings is a great break; pack snacks for longer stretches
- Couples Tips: Scenic drives along the Missouri River, date-night dinners in Bismarck
Route 3: From Montana (Billings or Miles City to Medora)
- Main Route: I-94 East from Billings/Miles City to Medora
- Must-See Stops:
- Miles City: Historic downtown, coffee shops
- Glendive: Makoshika State Park (badlands views, hiking)
- Wibaux: Small-town charm, local brewery
- Medora: Arrive ready for the TR Library and National Park
- Family Tips: Makoshika State Park is perfect for a picnic and short hike
- Couples Tips: Brewery stop in Wibaux, scenic photo ops along I-94
Road Trip Essentials & Quick Tips
- Plan fuel and food stops: There are long stretches without services, fill up and stock snacks in bigger towns
- Pack for changing weather: Even in summer, bring layers and sun protection
- Download offline maps: Cell service can be spotty in rural areas
- Add a playlist or podcast: Make the drive part of the fun (and listen to The Midwest Millennial Podcast for more tips!)
Make It Your Own
No matter where you start, you can mix and match stops, add detours, or stretch your drive over several days. The journey to the Theodore Roosevelt Presidential Library is half the adventure, so give yourself time to explore, try local food, and enjoy the wide-open spaces of the Northern Plains.
Related: Check out my 3-, 5-, and 7-day North Dakota road trip itineraries for more ideas once you arrive in Medora!
Plan Your Perfect North Dakota Adventure!
Want a custom North Dakota itinerary, designed just for you?
I now offer personalized trip planning sessions; choose from a detailed email itinerary or a live phone consultation (with a custom plan included). Whether you’re a foodie, history buff, or just want to make the most of your presidential library visit, I’ve got you covered!
Email Itinerary: $49
Phone Consult + Itinerary: $99
Ready to plan your Midwest getaway? Contact me here and mention “Trip Planning” in your message.
