In the Footsteps of Theodore Roosevelt

  • Badlands National Park + 11 more
  • Road Trips, USA Road Trips,
  • 15
from  £3,299pp
Book today

Introduction

Follow the remarkable journey of one of America’s most influential presidents on this unforgettable 15-day itinerary through the spectacular landscapes of the American West. Combining breathtaking national parks, authentic cowboy culture and iconic presidential landmarks, this unique itinerary traces the places that shaped Theodore Roosevelt’s passion for conservation and helped establish his enduring environmental legacy.

Your adventure begins in the authentic Western town of Jackson, Wyoming, before continuing through the magnificent scenery of Grand Teton and Yellowstone National Parks, where dramatic mountain landscapes, geothermal wonders and abundant wildlife showcase the natural beauty that Roosevelt fought so passionately to protect.

Travel onwards through Wyoming to Devils Tower National Monument, the very first National Monument designated by Roosevelt in 1906, before continuing to Medora, North Dakota, where Roosevelt’s years as a rancher transformed both the man and his vision for America’s wilderness. Here, you’ll explore Theodore Roosevelt National Park, visit the Theodore Roosevelt Presidential Library, and enjoy the famous Pitchfork Steak Fondue, overlooking the spectacular Badlands.

The journey continues into South Dakota’s beautiful Black Hills, where you’ll discover iconic landmarks including Mount Rushmore, Crazy Horse Memorial, Custer State Park, Wind Cave National Park and the dramatic landscapes of Badlands National Park. Along the way, enjoy scenic drives, abundant wildlife, authentic Western hospitality and classic Americana, including a visit to the legendary Wall Drug.

Blending spectacular scenery, fascinating history and Roosevelt’s extraordinary conservation legacy, this carefully crafted itinerary offers a unique opportunity to experience the landscapes that inspired one of America’s greatest presidents while discovering some of the most iconic destinations in the American West.

Tailor-made for YOU!

All of our itineraries are fully customisable and can be tailored to suit your individual preferences. Whether you’d like to start or end in a different city, upgrade your hotel accommodation, or add sightseeing excursions to enrich your experience, your Discover North America Travel Specialist is here to help.

Itinerary Flexibility

This itinerary can also operate in reverse, starting in Rapid City and ending in Jackson, Wyoming. Your Travel Specialist will be happy to tailor the route and travel arrangements to suit your preferred direction of travel, flight options, or schedule.

International Flights

We don’t include international flights in our headline prices as standard, as we work with a wide range of scheduled airline partners and offer flexible options to suit your preferences. Factors such as departure airport, airline, travel class, travel dates, and seasonal promotions can all impact the final fare. Your Discover North America Travel Specialist will take the time to understand your individual requirements and source the best-value flights tailored to your itinerary.

Find out more about the process we follow here.

 

Book today

Gallery

Itinerary

Days 1 & 2: Jackson, Wyoming

Welcome to Jackson, an authentic Western town nestled beneath the spectacular peaks of the Teton Range. After arriving, make your way to your hotel for a two-night stay.

Spend time exploring the famous town square with its iconic elk antler arches, browse the independent boutiques, galleries and Western outfitters, or relax in one of the many cafés and restaurants.

During your stay, wildlife enthusiasts may wish to join a safari in search of bison, moose, elk, bears and wolves, while those looking to embrace the Old West can enjoy horse riding, visit a working cowboy ranch or, if visiting at the right time of year, experience the excitement of the Jackson Hole Rodeo.

Alternatively, take the Jackson Hole Aerial Tram for breathtaking panoramic mountain views or enjoy a relaxing float trip along the Snake River.

Combining spectacular scenery, abundant wildlife and genuine Western hospitality, Jackson provides the perfect introduction to your American West adventure.

Day 3: Grand Teton National Park

Today, leave Jackson behind and journey into the spectacular landscapes of Grand Teton National Park, where you'll spend the night surrounded by some of the most dramatic mountain scenery in the United States.

Dominated by the jagged peaks of the Teton Range, the park is renowned for its crystal-clear lakes, alpine meadows, abundant wildlife and breathtaking viewpoints. Along the way, take time to stop at some of the park's most iconic locations, including Jenny Lake, Jackson Lake, Oxbow Bend and Snake River Overlook, each offering unforgettable views and excellent opportunities for photography.

The park is also one of the best places in the region to spot wildlife, with moose, elk, bison, pronghorn, black bears and bald eagles all regularly seen throughout the park.

Whether you choose to enjoy a scenic drive, take a leisurely walk along one of the many trails, or simply pause to admire the spectacular mountain vistas, Grand Teton National Park offers an unforgettable introduction to the natural beauty of the American West before continuing your adventure.

Days 4 & 5: Yellowstone National Park

Continue your journey into the world's first national park as you arrive in the legendary Yellowstone National Park for a two-night stay. Established in 1872, Yellowstone remains one of America's greatest natural treasures and was a place that deeply inspired President Theodore Roosevelt, whose passion for conservation helped shape the future of the United States' national parks.

During a visit to Yellowstone, it's easy to understand why Roosevelt became such a passionate advocate for protecting America's wild landscapes. As you explore the park's vast wilderness, abundant wildlife and extraordinary geothermal features, you'll be following in the footsteps of a president who believed these remarkable places should be preserved for future generations.

Over the next two days, you'll have the opportunity to discover many of Yellowstone's most iconic attractions. Witness the famous eruption of Old Faithful, marvel at the vibrant colours of the Grand Prismatic Spring, and take in the dramatic scenery of the Grand Canyon of the Yellowstone, where the powerful Lower Falls plunge into the canyon below. Other highlights include Mammoth Hot Springs, Norris Geyser Basin, West Thumb Geyser Basin, Yellowstone Lake and the bubbling mud pots and fumaroles found throughout the park.

Yellowstone is also one of the finest places in North America for wildlife viewing. Keep watch for bison, elk, wolves, bears, pronghorn, bighorn sheep and bald eagles as you explore the park's scenic roads and valleys, particularly the wildlife-rich Lamar Valley, often referred to as America's Serengeti.

With two days to immerse yourself in this remarkable landscape, Yellowstone offers an unforgettable opportunity to experience one of Theodore Roosevelt's greatest conservation legacies while discovering one of the world's most extraordinary national parks.

Day 6: Yellowstone National Park to the Ranch at Ucross, Sheridan

This morning, depart Yellowstone National Park and travel east through Wyoming's wide-open landscapes towards the historic town of Sheridan, where you'll spend the night at The Ranch at Ucross.

Nestled on a working cattle ranch beneath the Bighorn Mountains, The Ranch at Ucross offers an authentic taste of the American West. Rich in cowboy heritage and surrounded by rolling grasslands, it's the perfect place to slow down and experience the lifestyle that helped shape this part of the country.

After checking in, take time to explore the ranch, enjoy the peaceful surroundings and soak up the genuine Western hospitality. Depending on the season and ranch programme, you may have the opportunity to experience activities such as horse riding, wildlife viewing or simply relax on the porch while taking in the spectacular Wyoming scenery.

As evening falls, enjoy a hearty Western dinner and the unique atmosphere of a traditional ranch stay before continuing your Theodore Roosevelt-inspired journey through the American West.

Day 7: The Ranch at Ucross to Devils Tower National Monument

After breakfast, leave The Ranch at Ucross and continue your Theodore Roosevelt-inspired journey to one of America's most iconic natural landmarks – Devils Tower National Monument.

Rising dramatically 867 feet above the surrounding prairie, Devils Tower is instantly recognisable for its striking volcanic columns and deep cultural significance to many Native American tribes. The monument also holds a special place in American conservation history, as it became the first National Monument in the United States, designated by President Theodore Roosevelt on 24 September 1906 under the newly enacted Antiquities Act. Roosevelt's decision to protect Devils Tower marked the beginning of the National Monument system and reinforced his commitment to preserving America's most remarkable natural landscapes for future generations.

On arrival, take time to walk the Tower Trail, an easy circular path that provides excellent viewpoints of the monument while offering opportunities to spot prairie dogs, mule deer and a variety of birdlife. Visit the Visitor Centre to learn more about the tower's fascinating geology, Native American traditions and Roosevelt's role in safeguarding this extraordinary landmark.

Whether viewed from afar or explored on foot, Devils Tower is one of the American West's most awe-inspiring natural wonders and an essential stop on any journey following in the footsteps of Theodore Roosevelt.

Day 8: Devils Tower National Monument to Medora, North Dakota

Today, continue your journey north into North Dakota, travelling across the wide-open plains to the historic Western town of Medora, where you'll spend the next three nights.

Founded in the 1880s, Medora played an important role in Theodore Roosevelt's life, as it was here that he developed his deep appreciation for the American West and the conservation of its landscapes and wildlife.

Upon arrival, check into your accommodation and spend the remainder of the day at leisure. You may wish to explore the charming downtown area, browse its independent shops and galleries, or simply relax and soak up the authentic frontier atmosphere before discovering more of the region over the coming days.

Day 9: Theodore Roosevelt National Park & Pitchfork Steak Fondue

Today, we suggest spending the day exploring Theodore Roosevelt National Park, a landscape of colourful badlands, rolling prairies and rugged buttes that inspired Theodore Roosevelt during his time ranching in North Dakota in the 1880s. Following the deaths of both his wife and mother on the same day in 1884, Roosevelt sought solace in the Dakota Territory, and it was here that his passion for conserving America's natural landscapes truly began.

Take time to enjoy the park's scenic drives, walking trails and spectacular viewpoints while keeping watch for wildlife including bison, wild horses, elk, prairie dogs and mule deer. You may also wish to visit the Maltese Cross Cabin, Roosevelt's original ranch cabin, to gain a fascinating insight into his life on the frontier.

This evening, we recommend experiencing Medora's famous Pitchfork Steak Fondue. Set high above the town overlooking the Badlands, this unique Western dining experience features steaks cooked on pitchforks over an open flame and is the perfect way to end your day.

Day 10: Theodore Roosevelt Presidential Library & Medora Musical

Today, we suggest visiting the Theodore Roosevelt Presidential Library, where Roosevelt's remarkable life, presidency and conservation legacy are brought to life through immersive exhibits and interactive displays. The library explores his influence on the creation of America's national parks, forests, wildlife refuges and national monuments, offering a fascinating insight into one of the country's most influential presidents.

After your visit, enjoy the remainder of the day at leisure. You may wish to spend more time exploring Medora's charming downtown, browse its independent shops and galleries, or simply relax and soak up the authentic atmosphere of this historic Western town.

This evening, round off your stay in Medora with the world-famous Medora Musical, an open-air production celebrating the spirit of the American West through live music, dancing and spectacular performances set against the stunning backdrop of the North Dakota Badlands. It's the perfect finale to your time in the town that helped shape Theodore Roosevelt's enduring conservation legacy.

Day 11: Medora to the Black Hills, South Dakota

Today, leave Medora behind and journey south into South Dakota, travelling towards the spectacular Black Hills, one of the most scenic and historic regions of the American West.

Sacred to the Lakota people and renowned for its granite peaks, pine forests and winding scenic byways, the Black Hills offer a striking contrast to the open prairies and Badlands you've explored over the past few days. This remarkable region is home to some of America's most iconic landmarks and provides the perfect base for the next stage of your Theodore Roosevelt-inspired adventure.

Upon arrival, check into your accommodation and spend the remainder of the day at leisure. You may wish to explore the surrounding area, enjoy one of the region's scenic drives, or simply relax and take in the beautiful mountain scenery before discovering the Black Hills' many attractions over the coming days.

Day 12: Mount Rushmore, Crazy Horse Memorial & the Black Hills

Today, we suggest exploring some of the Black Hills' most iconic landmarks, beginning with the world-famous Mount Rushmore National Memorial. Carved into the granite face of the mountain, the monumental sculptures of George Washington, Thomas Jefferson, Theodore Roosevelt and Abraham Lincoln celebrate four of America's most influential presidents. For those following Theodore Roosevelt's story, seeing his likeness immortalised alongside the nation's other great leaders is a particularly fitting highlight of your journey.

Continue to the impressive Crazy Horse Memorial, an extraordinary mountain carving honouring the Lakota leader Crazy Horse. Still under construction, the memorial offers a fascinating insight into Native American history and culture through its visitor centre, museum and educational exhibits.

As you explore the region, take time to enjoy one or more of the Black Hills' spectacular scenic drives. The Needles Highway is renowned for its dramatic granite spires, narrow tunnels and sweeping mountain vistas, while the Iron Mountain Road offers winding curves, pigtail bridges and perfectly framed views of Mount Rushmore through its rock tunnels.

With its combination of iconic landmarks, breathtaking scenery and fascinating history, today provides another unforgettable chapter in your exploration of the American West.

Day 13: Custer State Park & Wind Cave National Park

Today, we suggest discovering two of South Dakota's natural highlights – Custer State Park and Wind Cave National Park.

Begin your day in Custer State Park, one of the largest and most beautiful state parks in the United States. Covering more than 71,000 acres, the park is renowned for its granite peaks, rolling prairies, crystal-clear lakes and abundant wildlife. Drive the spectacular Wildlife Loop Road, where you'll have an excellent chance of spotting the park's famous free-roaming bison herd, along with pronghorn, elk, bighorn sheep, wild burros and prairie dogs.

Continue to nearby Wind Cave National Park, home to one of the world's longest and most complex cave systems. Above ground, the park protects one of North America's last remaining mixed-grass prairies, providing an important habitat for bison, elk and other native wildlife. Join a ranger-led tour to explore the fascinating underground passages, famous for their unique boxwork rock formations found in very few places around the world.

Wind Cave National Park also holds a special connection to Theodore Roosevelt. Established in 1903, it became the seventh National Park in the United States during Roosevelt's presidency, reflecting his commitment to protecting America's unique natural landscapes. Visiting the park offers another opportunity to experience one of the many conservation successes that formed part of Roosevelt's remarkable legacy.

Day 14: Badlands National Park, Wall Drug & Rapid City

Today, leave the Black Hills behind and journey through the spectacular landscapes of Badlands National Park, one of America's most dramatic natural wonders. Carved by millions of years of erosion, the park is renowned for its colourful rock formations, towering pinnacles, deep canyons and vast prairie grasslands.

Take your time driving the scenic Badlands Loop Road, stopping at the many viewpoints to admire the breathtaking scenery while keeping watch for bison, bighorn sheep, prairie dogs and pronghorn antelope. Theodore Roosevelt travelled through this rugged landscape during his time in the Dakota Territory, and experiences such as these further strengthened his belief in preserving America's extraordinary natural places for future generations.

Before continuing to Rapid City, make a stop at the legendary Wall Drug. What began as a small roadside pharmacy in the 1930s has grown into one of South Dakota's most famous attractions, offering Western shops, restaurants, quirky attractions and plenty of opportunities to stretch your legs and experience this iconic slice of Americana.

Later, continue to Rapid City, where you'll spend the night. Often referred to as the gateway to the Black Hills, Rapid City offers a lively downtown filled with shops, restaurants and the popular City of Presidents walking trail, where life-sized bronze statues celebrate each of the United States' presidents. It's a fitting place to reflect on your Theodore Roosevelt journey.

Day 15: End of Your Theodore Roosevelt Adventure

Today marks the end of your Theodore Roosevelt-inspired journey through the American West.

Depending on your travel plans, you may choose to return your hire vehicle in Rapid City before beginning your journey home, or continue exploring North America with another unforgettable adventure.

If you're planning to extend your holiday, speak to your assigned Discover North America Travel Specialist, who can help create the perfect continuation of your itinerary. Whether you'd like to explore more of the USA or Canada, add another iconic national park, experience a scenic rail journey or enjoy a relaxing stay in a new destination, we'll be delighted to help you tailor the next chapter of your adventure.

We hope you've enjoyed following in the footsteps of Theodore Roosevelt, discovering the spectacular landscapes, historic landmarks and remarkable conservation legacy that helped shape the America we know today.