25 Best Road Trips in America
Nothing beats packing up the car, making some new playlists, downloading a few podcast series, and heading off for a road trip. Here are 25 of our favorites from sea to shining sea.
This day trip is available for only a few months each year when the snow is plowed and finally melts away in mid-June, but when that window opens jump through it to take a road trip out and back on Going-to-the-Sun Road in Glacier National Park in Montana. You may see a family of bears crossing the street or a mountain goat or two hanging out in their natural habitat, and you definitely will see a slew of epic waterfalls (including the most beautiful ones in the state), sweeping vistas made for your smartphone’s pano mode, and massive conifers along this showstopper of a road. If you are staying at the magnificent West Glacier KOA, the start of Going-to-the-Sun Road is close enough (3-miles away) that you may want to make this 2-4 hour trek multiple times because it’s truly spectacular and unlike any other 50-mile stretch of asphalt in America.
Kentucky bourbon trail (with a designated driver)
“Traveling the Kentucky Bourbon Trail can take three days or two weeks. It is whatever you make it,” shares respected travel writer Jason Greene of One Good Dad fame. “Some stop by the gift shops and that’s enough for them. Others, like my brother-in-law and I, we wanted to take a distillery tour at each location we visited.” Greene points out that, “each distillery offers a history lesson, discusses how their bourbon differs from others and offers the happy ending of a bourbon tasting.” Having a designated driver each day of your road trip makes this possible. For a luxurious, Instagram-worthy place to stay during your bourbon trail road trip, check into the Kentucky Castle in, appropriately enough, the city of Versailles.
Oregon’s Splendor and the California Redwoods
Start in Portland with more Pip’s mini artisan doughnuts than seems wise (it’s okay, they are so small!) and a Timbers or Thorns soccer match at newly renovated and reopened Providence Park. Next, head east on the Historic Columbia River Highway for a bevy of cascades including legendary Multnomah Falls. Bring your swimsuits and towels because many of the waterfalls have wading pools to cool off and pose for photos with the rushing water overhead. Hang a right on Route 35 to start south toward Mt. Hood for a hike and to Bend, Oregon for a great meal at McKay Cottage. Continue to Crater Lake, for a drive along the rim road and maybe a hike down to the water. You’ll soon reach the majestic California Redwoods—Star Wars’ fans take note: this park was the stand-in for the forest moon Endor. Go as far south as Fern Canyon for a mystical short hike and an afternoon spent on the wild Pacific beaches there. Start driving north again but this time hug the rugged Oregon coastline with massive sand dunes until you reach Tillamook Creamery back up near Portland. Along the way, you will have experienced a diverse array of nature, city life, sports, and tasty cheeses.
Cross country one way: Northern route
It’s both the classic American road trip and one of the best road trips you can take, especially with kids in tow. From personal experience, we recommend a one-way cross-country trek and doing it in a minivan. Make this journey in two weeks, in either a Kia Sedona and Toyota Sienna, because a minivan provides ample room for all your people and all the stuff your people will accumulate, and yet is still capable of navigating city streets with ease, unlike a camper van or RV. The best northern route starts in Seattle and travels east with a heavy dose of National Parks to start (Glacier, Yellowstone, Grand Tetons) before making your way to Minneapolis for some charming Midwestern city life and an organic, locally-sourced yet Nordic-inspired dinner at The Bachelor Farmer. Next, pay a visit Frank Lloyd Wright’s first Usonian home, Jacobs I, in Madison Wisconsin, before moving on to a big city adventure in Chicago on the shores of Lake Michigan. Proceed to loop around the lake to spend time among Holland, Michigan’s tulips and windmills, then rock out at the Rock-n-Roll Hall of Fame in Cleveland before finishing in either historic Philadelphia or on Coney Island in NYC.
Cross country one way: Southern route
Starting on the East coast this time, from maybe Atlanta or Washington, D.C., travel through Memphis for BBQ and the National Civil Rights Museum. Then spend a night or two in St. Louis at the elegant Curio Collection Hilton Union Station Hotel specifically so you and the fam can visit the City Museum which remains the best place in America to be a child (of any age), and take a fun trip up into the Gateway Arch. Make the famously flat and tedious trek across Kansas (if only to be able to expertly make the ‘this is as boring as driving across Kansas’ joke) to reach Denver for a night of vintage amusements at Lakeside and to see a concert at the Red Rocks Amphitheater. From there, pass through Aspen before dipping down into southern Utah for a bevy of stunning National Parks (Bryce Canyon, Arches, Zion), then make the toasty crossing through Death Valley, spend a clear night gazing at the stars in Joshua Tree, and finish up with a ride on the Ferris wheel on the Santa Monica Pier.
Midwest baseball road trip
Many of America’s best ballparks are situated within easy drives of each other in the Midwest making a baseball road trip easy and amazing, anytime from late March to early October. Start at PNC Park in Pittsburgh to cheer on the Pirates, then make your way through Cleveland and Detroit, before finding your way to Chicago to experience the magic of Wrigley Field and the Cubs before tasting a bratwurst in Milwaukee and heading up north to Minneapolis to see the Twins. If the schedules for the MLB teams don’t align perfectly, fill in the gaps with minor league baseball games (there are many teams scattered across the Midwest from Indianapolis, Toledo, Columbus, St. Paul and beyond) to score better value on ticket prices and concessions while watching the stars of tomorrow play ball. Along the way, root root root for the home teams, enjoy adult beverages of your choice, and let your kiddos turn their tongues pink with cotton candy as you partake in America’s pastime. Before you go, find out how 25 of the MLB teams got their names.
Million Dollar Highway
Drop Zone Drone/shuterstock
Toeing the line between dangerous and thrilling, this 25-mile stretch of winding road spanning parts of southwest Colorado and New Mexico is lined with ghost towns, hot springs, National Forests, mountains, and the city of Durango, one of the prettiest small towns in America and the place where Butch Cassidy and the Sundance Kid was filmed. This best road trip can be done in a single day, providing that day is in season, because you will be traveling from an elevation of 6,200-feet near Durango to over 11,000-feet when crossing Red Mountain Pass.
Pack your passport for this great northern adventure because while most of this road trip occurs in the United States, you will cross over into the wild west of Canada’s Yukon Territory when you drive north from Skagway on the stunningly panoramic Klondike Highway. This choose-your-own-adventure out-and-back road trip can be completed in a day (even during a Carnival cruise to Alaska because there’s an Avis within walking distance of the port) and will provide you with unique memories and photo ops. During this spectacular road trip, you’ll pass the curious Carcross Desert and reach the marvelously glowing green Emerald Lake before making the return drive back to Skagway for a tasty fresh-caught local halibut during lunch at Olivia’s Restaurant at the Historic Skagway Inn.
With the smell of salt air blowing through your car windows from all directions, a leisurely road trip on the Cape provides you with true rest and relaxation while “seeing what Cape Cod looked like before tourists discovered it.” Route 6A’s website goes on to point out that, “many of the homes and churches along this tree-shaded road are listed on the National Register of Historic Places,” giving you the chance to visit and spend time in some of the oldest towns, with the quaintest shops and restaurants in America during a Cape Code road trip from Mashpee to Provincetown.
The Overseas Highway
The Overseas Highway, built atop a former railroad over a century ago, crosses 42 bridges, including the Seven-Mile bridge over Pigeon Key as it goes south from Miami to Key West. Road trippers traveling this most southern leg of Route 1 should plan to exit the highway frequently to experience island life and stretch this easy one day drive out over several. Visiting the Florida Keys via the Overseas Highway is more about the journey than the destination. As Trip Savvy puts it, “today, motorists can travel the highway in less than four hours from Miami. However, drivers should allow time to experience the natural beauty of the ever-changing scenery of the seas and wilderness bordering the roadway, and the magnificent sunrises and sunsets.” Before you tackle the Overseas Highway, consult this road trip checklist for your car.