Yellowstone & Cowboy Country Road Trips
Boasting spectacular National Parks, cowboy towns that feel like they’ve been lost in time, an abundance of wildlife and quirky roadside attractions along stunning highways and byways, Yellowstone and Cowboy Country makes for an epic road trip.
What are the highlights of a Wild West road trip?
National Parks: There are six National Parks across the region, all boasting entirely different but similarly spectacular landscapes:
- Glacier National Park, Montana
- Yellowstone National Park, Wyoming
- Grand Teton National Park, Wyoming
- Badlands National Park, South Dakota
- Wind Cave National Park, South Dakota
- Theodore Roosevelt National Park, North Dakota
Wildlife: Yellowstone and Cowboy Country is one of the best places in America for wildlife encounters. Across much of the region, you can spot bison, elk, moose, bighorn sheep, bald eagles, and even wolves.
Black and brown bears can be found in the Rocky Mountains and Yellowstone, and you can see grizzly bears in Glacier National Park, although sightings are more rare.
Western Towns & Ranches: Immerse yourself in cowboy life on a road trip through the Wild West. There is a huge variety of Guest Ranches across the region, where you can horse ride through stunning landscapes and experience real ranch life. Towns like Cody, Buffalo, Deadwood and Medora all showcase Old West charm, with streets steeped in history, lively saloons and rodeos.
Route 66 & Roadside Attractions: Along the entirety of Route 66, you’ll find quirky art installations and museums. In 2026, this iconic journey is celebrating its 100th anniversary, which means there will be even more going on You can expect towns along the route to host classic car parades, festivals and historical exhibitions.
You can find unique roadside attractions scattered throughout the rest of the region too, including South Dakota’s renowned Wall Drug Store and the ‘Corn Palace’, or North Dakota’s ‘Enchanting Highway’.
Where is the best place to start my road trip?
For Ranches: Flying into Jackson, Wyoming, puts you within a few of hours of a variety of Guest Ranches, whether you’d like to explore Yellowstone National Park, or the wide open landscapes of Wyoming and Montana.
For National Parks: With great flight options from the UK, Denver in Colorado is a great starting point for a National Parks road trip. From Denver, you’re just a stone’s throw away from Rocky Mountain National Park, and then we’d recommend either heading towards Badlands, then Theodore Roosevelt, or winding through the charming cowboy towns of Wyoming, making your way to Yellowstone.
For History: South Dakota’s Rapid City, makes a great starting point if you’re interested in history. Enjoy easy access to Mount Rushmore and the Crazy Horse Memorial from the city, and you can then get a window into the Old West visiting the towns of Deadwood and Medora.
For Route 66: Iconic Highway 66 starts in Chicago and ends in Santa Monica. You can start at either end, and we’d recommend two to three weeks to do the whole route. If you’re short on time, you can drive either the East or the West half, with Dallas marking a convenient mid-point for either beginning or ending your journey.
How long do I need for a road trip in this region?
We’d recommend two to three weeks for a road trip in Yellowstone and Cowboy Country. This is long enough to do the entirety of Route 66, to visit several National Parks, and to include a ranch stay or two.
Plan your holiday
