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  • Boating at Prineville Reservoir State Park in Central Oregon
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    Central Oregon: Great Views and a Fun Resort

  • View of Portland, Oregon, and Mount Hood as seen from Washington Park
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    Portland, Oregon: Shop, Sightsee and Eat a Doughnut

  • View of Casper, Wyoming, from the National Historic Trails Interpretive Center
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    Casper, Wyoming: Western Wear, Art and Good Vibes

  • Neon signage illuminating the Mint Bar in Sheridan, Wyoming
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    Bighorn National Forest and Sheridan, Wyoming: Go Explore

  • Hiking near Devils Tower National Monument in Wyoming
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    Devils Tower National Monument and More Scenic Places

  • A model of Crazy Horse Memorial in front of the monument in progress in South Dakota
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    South Dakota’s Major Memorials and Custer State Park

  • Hiking in Badlands National Park in South Dakota
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    Rapid City and Badlands National Park, South Dakota: A Fitting End

Spotting bison along the drive through Custer State Park, South Dakota
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Oregon, South Dakota and Wyoming: Natural Wonders and Monumental Sites

By Christi Womack

  • Route distance:
    3,490 km
  • Suggested Time:
    1-2 weeks

Get ready for a fast-paced, fly-drive trip featuring beautiful landscapes and diverse experiences in three Pacific and Western U.S. states.

Seven jam-packed days of adventures await in Oregon, Wyoming and South Dakota. After arriving at Portland International Airport (PDX), follow this day-by-day itinerary that leads to must-visit places, including exciting (and charming) cities, mountain ranges and national treasures such as monuments and memorials. Whether you like traipsing through a forest, learning about local history or simply sipping a craft brew in a cozy lodge, this trip is for you.

01
Boating at Prineville Reservoir State Park in Central Oregon
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Central Oregon: Great Views and a Fun Resort

On the first morning of your trip in Oregon, rent a car at Portland International Airport and drive southeast on U.S. 26 heading to Prineville Reservoir State Park. The trip takes about three and a half hours, so you’ll want to take a break along the way to stretch your legs and get a bite to eat – Mt. Hood Village or Warm Springs are good options. Once you reach Prineville Reservoir, pick up a map to help plan your afternoon at the high-desert park. Go hiking on the 4.3-kilometer Chimney Rock Trail; it’s an easy path with a views of a dry creek bed, canyons and the snow-topped Cascade Mountains. Reserve enough time to make the one-hour drive to Pronghorn Resort, an incredible luxury property in Bend. After checking in to your room at the Huntington Lodge, you’ll enjoy activities that could include a round of golf on one of two world-class courses or a sunset tour of the ancient Lava Cave – it’s a favorite spot where couples become engaged. End your day with a Tuscan-themed dinner with wine at Cascada, then sip a microbrew or craft cocktail inside The Coyote bar or relax outdoors by the patio fire.

264 km
3.5 hours by car
02
View of Portland, Oregon, and Mount Hood as seen from Washington Park
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Portland, Oregon: Shop, Sightsee and Eat a Doughnut

Catch the sun rising in grand fashion over the Cascade Mountains and eat breakfast at the lodge’s Trailhead Grill before the 3.5-hour return to Portland via U.S. Highway 97 and U.S. Highway 26. This will be a great day to get an introduction to Portland, Oregon’s hip, one-of-a-kind capital city. Your first stop in the city is the trendy Nob Hill neighborhood, filled with lovely Victorian buildings, shops and an array of restaurants. Eat lunch here before heading to Washington Park, a sprawling hilltop playground with one of the best views of the city. Within the park, see a colorful array of flowers in the International Rose Test Garden, then wander the tranquil paths of the lushly manicured Portland Japanese Garden. After seeing the sights, go shopping in Old Town Chinatown, which is Portland’s oldest neighborhood and original downtown. Follow paths through the Lan Su Chinese Garden, then step inside one of the excellent restaurants to drink traditional tea and eat authentic fare. It’s time to head to your comfortable accommodations at Embassy Suites by Hilton Portland Downtown, but you’ll want to make one last stop in Chinatown. Visit the renowned Voodoo Doughnut shop – it’s open 24 hours – and buy a sweet treat or two to enjoy in the morning during the drive to the airport.

1791 km
4.5 hours by plane
03
View of Casper, Wyoming, from the National Historic Trails Interpretive Center
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Casper, Wyoming: Western Wear, Art and Good Vibes

This morning, return to the Portland airport to return your rental car and board a flight to Casper-Natrona County International Airport in Wyoming. Rent a car for the 24-kilometer drive to your accommodations at the Best Western Plus Casper Inn & Suites. Spend the afternoon discovering all there is to see and do in this mountain town. Stroll Historic Downtown Casper and be sure to visit the town’s hub of activity, the David Street Station, popular for community events and festivals. During your walking tour, admire murals on buildings and sculptures, and pop into Lou Taubert Ranch Outfitters to buy a cowboy hat. Visit the National Historic Trails Interpretive Center to learn more about Casper’s Old West beginnings. After stopping for dinner – perhaps steak, pizza, Mexican fare or American pub food – choose from an array of breweries, distilleries, bars and coffee shops to enjoy a drink and the local vibe. Don’t stay up too late, though, as you’ll want to get rest for the busy day ahead.

195 km
2.25 hours by car
04
Neon signage illuminating the Mint Bar in Sheridan, Wyoming
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Bighorn National Forest and Sheridan, Wyoming: Go Explore

Start your day with a hearty meal of breakfast tamales or eggs Benedict from Eggington’s, then pick up provisions for a picnic lunch to eat later today. Drive 193 kilometers, about a two-hour trip, to Bighorn National Forest, which was named after the Bighorn River and offers over 1,900 kilometers of trails with stunning scenery. To get information about the forest, stop at its one visitor center, the Shell Falls Interpretive Site. Go hiking on the 7.6-kilometer Tongue River Canyon Trail, which starts among shear limestone walls and leads to beautiful views of tributary canyons, wildflowers, lodgepole pines and aspen trees. Find more incredible vistas along 185 kilometers of three forest routes, the Bighorn Scenic Byway, Medicine Wheel Passage or Cloud Peak Skyway. Keep your eye on the time. As daylight wanes, drive 45 minutes to charming Sheridan in the Bighorn Mountain Range. After checking in at the Hampton Inn Sheridan, wander around the Old West town and find a place to eat dinner; downtown eateries range from cafes to brewpubs to steakhouses. Enjoying hanging out with the locals in the iconic Mint Bar, open since 1907, or Black Tooth Brewery, serving award-winning craft beer since 2010.

409 km
5 hours by car
05
Hiking near Devils Tower National Monument in Wyoming
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Devils Tower National Monument and More Scenic Places

Just like yesterday, you’ll want to eat breakfast, check out of your hotel and buy items for a picnic lunch to eat later today. Drive 240 kilometers, about 2.5 hours, to Keyhole State Park, which is easily accessible from Interstate 90. Hike the 2.5-kilometer, paved Marina Trail, which leads through the forest to amazing views of Keyhole Reservoir. Experienced boaters should consider renting a boat to go fishing to catch and release walleye, catfish, bass or pike. Enjoy the 35-minute drive to Devils Tower National Monument. Hike the paved, 2-kilometer Tower Trail around the base of the massive formation that rises over 386 meters from the prairie land. Expert climbers love the challenge of scaling the cracks and columns. In addition to views of the tower, see the boulder field and surrounding landscape. Snap some photos at the Devils Tower Scenic View overlook point. If you have time, consider booking a horseback riding excursion with Andy’s Trail Rides or another tour operator in the heart of the Black Hills of South Dakota – or drive two hours and check in to the Best Western Golden Spike Inn & Suites in Hill City. Enjoy dinner nearby; options include wood-fired pizza at Mangiamo, American fare at Desperados or European-inspired fine dining at Alpine Inn.

166 km
3 hours by car
06
A model of Crazy Horse Memorial in front of the monument in progress in South Dakota
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South Dakota’s Major Memorials and Custer State Park

Today, you’ll visit three iconic places in South Dakota’s Black Hills and Badlands region. After a 25-minute drive, start your morning at the Crazy Horse Memorial. Check out three on-site museums, film and cultural programs telling the story of the area’s Indigenous Americans, including the Lakota warrior Crazy Horse. View the mountain carving in progress from the wall of windows and outdoor viewing veranda. Stay here to eat lunch at the Laughing Water Restaurant. Next, spend 30 minutes driving 28 kilometers to Mount Rushmore National Memorial. Walk the Presidential Trail for closer views of the memorial, which features the faces of four American presidents – George Washington, Thomas Jefferson, Theodore Roosevelt and Abraham Lincoln – carved into the side of the mountain. Step inside the visitor’s center and sculptor’s studio. Enjoy café snacks or ice cream, and stop in the gift shop to purchase souvenirs to take home. Next, drive to Custer State Park, about 32 kilometer