13-Day Adventure: Denver to Jackson Hole

Thirteen days from Denver, Colorado to Jackson Hole, Wyoming — five national parks, the Black Hills, the North Dakota Badlands and a string of historic Western towns. The route works its way north from Denver through South Dakota to Medora and the Theodore Roosevelt Presidential Library, west into Yellowstone, and south to the Tetons before turning back toward Colorado.

Here is a day-by-day plan. Distances and drive times are approximate; check seasonal road and park closures before you go.

The stage and red sandstone formations of Red Rocks Amphitheatre outside Denver, Colorado

Day 1: Arrive in Denver, Colorado

  • Explore Denver’s art, history and culture — the Denver Art Museum, Union Station and Red Rocks Amphitheatre.
  • Stay / eat: The Crawford Hotel; Guard and Grace.

Overnight in Denver, CO

The painted exterior of Evans Plunge, the warm spring-fed pool in Hot Springs, South Dakota

Day 2: Travel to Hot Springs, South Dakota

  • Relax in the warm spring-fed pools of Evans Plunge and stroll the Freedom Trail.
  • Stay / eat: The Red Rock River Resort & Spa; Whiskey River.

~6 hours, 370 miles · Overnight in Hot Springs, SD

A herd of bison grazing beside the Wildlife Loop Road in Custer State Park, with a car stopped among them

Day 3: Fossils & caves

  • The Mammoth Site fossil beds and Wind Cave National Park.
  • Wildlife spotting at Custer State Park.
  • Visit the Crazy Horse Memorial.
  • Stay / eat: K Bar S Lodge; The Powder House.

~1.5 hours, 60 miles · Overnight in Custer / Keystone, SD

Aerial view of the Mount Rushmore carving in the granite of the Black Hills, surrounded by ponderosa pine

Day 4: Rushmore & Deadwood

  • Marvel at Mount Rushmore.
  • Drive scenic Spearfish Canyon.
  • Step into Old West history in Deadwood.
  • Stay / eat: Historic Bullock Hotel; Jacobs.

~2.5 hours, 95 miles · Overnight in Deadwood, SD

Devils Tower rising above the pine forest of northeastern Wyoming, the first national monument in the United States

Day 5: Devils Tower to Medora, North Dakota

  • Explore Devils Tower National Monument, the nation’s first, established by Theodore Roosevelt in 1906.
  • Continue north to Medora, ND.
  • Stay / eat: Rough Riders Hotel; Little Missouri.

~5.5 hours, 310 miles · Overnight in Medora, ND

The Theodore Roosevelt Presidential Library on the butte above Medora, with the badlands below and storm clouds overhead

Day 6: Medora & the Roosevelt legacy

  • Tour the Theodore Roosevelt Presidential Library; explore the exhibits and the landscape they sit in.
  • Enjoy a Pitchfork Steak Fondue dinner, followed by the Medora Musical.

Overnight in Medora, ND

Two children hiking a trail at Painted Canyon in Theodore Roosevelt National Park at sunset

Day 7: Theodore Roosevelt National Park

  • Wildlife, scenic drives, Painted Canyon, Wind Canyon Overlook and the Petrified Forest.
  • Take a boxed lunch from the Library into the park.

Overnight in Medora, ND

The Yellowstone River winding through open valley below snow-capped mountains near West Yellowstone, Montana

Day 8: Journey to Yellowstone

  • A scenic drive along the Yellowstone River to the park’s North Entrance.
  • Stay / eat: The Roosevelt Hotel Yellowstone; Iron Horse Bar and Grill.

~7 hours, 450 miles · Overnight in Gardiner, MT

Aerial view of Grand Prismatic Spring in Yellowstone National Park, its blue centre ringed with orange bacterial mats

Day 9: Yellowstone wonders

  • The Roosevelt Arch, Mammoth Hot Springs, Norris Geyser Basin, Grand Prismatic Spring and Old Faithful.
  • Stay / eat: The Old Faithful Inn, the iconic 1904 log-and-stone lodge, with classic dining service.

Overnight in Yellowstone / West Yellowstone, MT

A waterfall plunging into the Grand Canyon of the Yellowstone between steep canyon walls

Day 10: Canyon & lake region

  • Discover Yellowstone’s Lake Region, the abundant wildlife of Hayden Valley, and the cascading waterfalls of the Grand Canyon of the Yellowstone.
  • Stay / eat: Old Faithful Inn; Wylie’s Canteen at Lake Lodge.

Overnight in Yellowstone / West Yellowstone, MT

The Teton Range reflected in the Snake River at Oxbow Bend, Grand Teton National Park, in autumn

Day 11: Grand Teton National Park

  • Jenny Lake, Teton Park Road and the Chapel of the Transfiguration.
  • Stay / eat: The Wort Hotel, with its western art collection and the Silver Dollar Bar & Grill.

~2.5 hours, 100 miles · Overnight in Jackson Hole, WY

The Snake River bending through pine forest with the Teton Range on the horizon, seen from Snake River Overlook

Day 12: Snake River & Jackson Hole

  • Take a scenic float trip on the Snake River, surrounded by the towering peaks of the Teton Range.
  • Explore downtown Jackson Hole’s shops, galleries and western charm.
  • Optional: end the day with the Bar T 5 Covered Wagon Cookout — cowboy music, hearty food and laughter.

Overnight in Jackson Hole, WY

The Denver skyline at sunset above a green city park in Colorado

Day 13: Return to Denver

  • A scenic drive through southern Wyoming via Rock Springs and Rawlins.
  • For a more relaxed pace, overnight at the Hotel Wolf in Saratoga, a classic western inn, and dine at the Aspen House Restaurant in a restored Victorian home.

~8 hours, 510 miles

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