25 Best Stops on an Epic Cross-Country America Road Trip
The Great American Road Trip is just as much a part of Americana as the stars and stripes. While in yonder years, Route 66 dominated as the iconic drive, today, the cross-country road trip reigns supreme. We mapped out a 10-day itinerary—including top city sights and national parks between Washington, D.C. to Washington State—so you can make the best of your journey west.
Chelsea is Brooklyn-based travel writer, editor, and photographer. When not home eating her way through NYC, she's gallivanting across the globe, sailing the coast of Croatia or hiking the peaks of Peru. Her superpowers include booking flight deals and sleeping in small plane seats.
Day 1: 263 miles from Washington D.C. to Pittsburgh
Once you’ve gotten your fill of America’s capital, it’s time to hit the road heading west. About three and half hours in, you’ll pass by Fallingwater, the renowned residence designed by Frank Lloyd Wright that sits cantilevered over a bucolic waterfall in rural Pennsylvania. The grounds are maintained year-round, with the original 1930s custom furniture and artwork still on display. From here, you’re just 75 minutes outside Pittsburgh. Upon arriving in Steel City, drop your bags at the Ace Hotel Pittsburgh—a refurbished century-old YMCA turned hip hotel in the up-and-coming East Liberty neighborhood—then follow the in-the-know crowd to Smallman Galley, a restaurant incubator with four rotating food concepts from a line-up of rising chefs. This season, there’s Detroit-style pizza, Vietnamese cuisine, Latin-fusion tapas, and innovative takes on American classics.
Day 2: 460 miles from Pittsburgh to Chicago
While the second half of this cross-country adventure focuses on the scenery, the eastern side is all about the cityscapes. Divide today’s day-long trek to Chicago with a pitstop in Cleveland, just two hours west of Pittsburgh. Here, grab a bite to eat at the West Side Market before wandering through the Rock and Roll Hall of Fame to see guitars and paraphernalia from music legends like Jimi Hendrix, Pink Floyd, and Mick Jagger.
You’re going to want to pick up some gift shop snacks, because it’ll be another five hours before you pull into the Windy City. In Chicago, bed down at the Viceroy Chicago on the glitzy Gold Coast, whose opulent interiors are done up in Art Deco elements that nod to the hotel’s past as the 1920s Cedar Hotel. The real showstopper is the 18th-floor rooftop overlooking the Magnificent Mile and Lake Michigan.
Day 3: 147 miles from Chicago to Madison, Wisconsin
A two-and-a-half-hour drive from Chicago brings you to Wisconsin’s charming college town of Madison. This untapped Midwest gem is home to locavore restaurants, indie boutiques, and contemporary art galleries. Follow the locals to Sophia’s Bakery & Café, where mouthwatering cottage cheese pancakes are served in a cozy dining room. The nearby Chazen Museum of Art and the Madison Museum of Contemporary Art have impressive collections, but if you’d rather spend the day indulging in some retail therapy, check out Upshift for flirty vintage dresses or Anthology for quirky handmade crafts. There’s no better place to have dinner than the James Beard award-winning L’Etoile Restaurant, where chef Tory Miller—you may have seen him on Iron Chef Showdown—serves locally sourced dishes like Blue Valley Gardens duck breast with Swiss chard and soubise.
Day 4: 775 miles from Madison to Rapid City, South Dakota
Today is the longest stretch you’ll be on the road, so crank those tunes and prepare to cruise straight through Wisconsin, Minnesota, and South Dakota on I-90. Stretch your legs in Badlands National Park, an otherworldly expanse of jagged pink pinnacles, grass prairies, and ancient fossil beds. While rhinos, wild horses, and saber-toothed cats used to roam this wild terrain, today you’re more likely to spot bison, bighorn sheep, and prairie dogs. Backcountry camping is available for the truly adventurous; others can set up at Cedar Pass Campground (which offers running water, toilets, and covered picnic tables) or the park’s eco-friendly cabins, which come outfitted with pine-wood beds, flatscreen TVs, and mini-fridges and microwaves.
Day 5: 533 miles from Rapid City to Jackson, Wyoming
It’s early to rise on day five if you want to beat the crowds for an early-morning visit to Mount Rushmore national monument, just 20 minutes away. After taking in the Presidents’ massive granite profiles, continue on through the gorges, canyons, and cliffs of the Black Hills National Forest. Once you’re out of South Dakota, you’ll cut through the heart of Wyoming, passing endless plains and the sprawling Wind River Reservation. Tucked between the Teton and Gros Ventre mountains, Jackson blends Wyoming’s rustic, rough-and-tumble side with a refined resort town vibe. The Anvil Hotel is a perfect example of this fusion: the redesigned 1950s motel reflects the region’s rugged past with a mountain-modern twist. Stylish interiors, courtesy of Brooklyn-based firm Studio Tack, are done up with brass fixtures, custom iron bed frames, and Woolrich blankets. After settling in, make a dinner reservation at Glorietta if you’re in the mood for Italian. The roasted acorn squash; ricotta cavatelli with spicy sausage, brown butter, and fried sage; and zeppole topped with mascarpone and strawberry compote come highly recommended.
Days 6-8: 426 miles from Jackson to Missoula, Montana
Get your cameras ready: the next few days are all about epic Rocky Mountain scenery, from Wild West backcountry to lush, lakeside meadows. Before leaving Jackson Hole, fuel up with homemade pastries or bread pudding french toast at Persephone Bakery, then set your GPS for Grand Teton National Park. This 310,000-acre swath encompasses Jackson Lake, Snake River, and the entire Teton range, which is webbed together by more than 200 miles of hiking trails. Just 10 miles north on 191, you’ll enter Yellowstone—America’s first national park famous as much for its rainbow-colored hot springs, mud pots, and spewing geysers as it is for picture-perfect wildlife sightings (keep your eyes peeled for bison, moose, black bears, elk, and the rare wolf pack).
After Yellowstone, cross the border into Montana’s Big Sky country and continue north past dude ranches, whitewater rapids, and vast cerulean skies as far as the eye can see. Home for the night—the Resort at Paws Up, a 37,000-acre working cattle ranch and luxe retreat in the Blackfoot Valley—is just a half hour east of Missoula. Take your pick between a private log cabin or riverfront glamping tent, which comes with its own chandelier, copper soaking tub, and on-call butler and chef, who will happily cook up whole-roasted rainbow trout or chili-dusted Black Angus prime rib. Although there’s world-class fly fishing, ATVing, and rock climbing on offer, horseback riding is the resort’s beating heart. Embrace your inner cowboy (or girl!) at the Saddle Club, whose 29,000-square-foot arena and more than 100 miles of trails make it the largest private equestrian center in Montana. The on-site wranglers can also arrange rodeo lessons, cattle drives, and dinners aboard traditional chuckwagons.
RELATED: 8 Best Dude Ranches in Montana
Days 9-10: 685 miles from Missoula to Seattle
Before heading west to your final destination, it’s worth making one last detour to see Montana’s stunning Glacier National Park. You can take in the scenery—crystalline, glacier-fed lakes; sheer, snow-capped peaks; untouched alpine meadows—along the gorgeous Going-to-the-Sun Road, a 50-mile route that crosses the Continental Divide and winds through Logan Pass alongside Saint Mary Lake. Heads up: be prepared to pull over to make way for mountain goats!
After (reluctantly) leaving the mountains of Montana, hop back on I-90 to enter the northern tip of Idaho. This short sprint overlooks steep gorges and straddles the shores of Lake Coeur d’Alene before entering Washington via Spokane. The final four-hour leg to Seattle is pretty barren, so make sure you have your road trip playlist queued up for some carpool karaoke. You know you’re getting close to the coast when you hit Snoqualmie Pass, just 55 miles outside the Seattle. The drive cuts through the Cascade Mountain Range, home to towering evergreen forests, misty mountaintops, and thundering waterfalls.
Once you reach the city, you deserve to put your feet up at The Nest, Thompson Seattle‘s rooftop bar, for sundowners and sweeping views of Puget Sound, Mount Rainier, and the Seattle cityscape. Cheers!
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