7 Unforgettable U.S. Cross-Country Road Trips

This article was originally published in 2023 and most recently updated on July 3, 2026, with current information.

The beloved road trip truly celebrates the journey itself, indulging in the miles upon miles it takes to get from one place to the next. While there are endless road trip options out there—themes include national parks, electric vehicle-friendly travel, and everything in between—the cross-country road trip arguably captures people’s imagination the most, with legendary roadways like Route 66 forming an integral part of the country’s history.

Many landscapes have changed over time, but the love of a small-town diner, quirky roadside attraction, and neon-lit motel remains firmly cemented in American culture. If you’re overdue for an adventure, here are seven cross-country road trips that will hopefully inspire a desire to see part of the United States you haven’t seen before.

1. Route 66

Photo by Karolis Kavolelis/Shutterstock

• Start: Chicago, Illinois
• End: Santa Monica, California
• Distance: 2,448 miles

“66 is the mother road, the road of flight,” John Steinbeck wrote in his Pulitzer Prize–winning novel, The Grapes of Wrath. The road from Chicago to California is the most famous drive in the nation, even though it was technically removed from the U.S. Highway System in 1985. Drivers can still make this more than 2,000-mile drive (celebrating its centennial in 2026) on their own, starting in Chicago and then hitting cities like St. Louis, Oklahoma City, and Santa Fe before finishing in Santa Monica. Along the way, the changing western landscape unfolds—from plains to desert to coast.

Route 66 has plenty of sights, from the artistic Cadillac Ranch in Amarillo, Texas, to downright breathtaking detours. (Grand Canyon, anyone?) The drive is nearly 2,500 miles, so you can tailor it to your interest: One particular itinerary focuses on the American pastime of drinking whiskey, stopping at craft distilleries like Few Spirits in Chicago, Still 630 in St. Louis, and Red Fork Distillery in Tulsa.

2. U.S. Route 2

Photo by Gottography/Shutterstock

• Start: Houlton, Maine
• End: Everett, Washington
• Distance: 2,575 miles

Bring your passport or passport card for this one. This cross-country trip mostly parallels the northern border of the United States, with a brief section crossing through Canada in between Vermont and Michigan. Road-trippers start in Houlton, Maine, and continue west on U.S. Route 2 until right before the Canadian border near Burlington, Vermont.

Going through Canada, travelers pass through Québec and then Ontario via the Trans-Canada Highway. This section spotlights some of Canada’s Great Lakes scenery, including Pancake Bay Provincial Park’s beach and the 40-foot Kakabeka Falls in Thunder Bay. But cities like Montreal and Ottawa are also along the way and warrant a weekend full of exploration in Canada’s historical and cultural hubs.

Once the route rejoins the USA in St. Ignace, Michigan—across from Mackinac Island State Park—there are still plenty of wild spots to see. The Apostle Islands National Lakeshore in Wisconsin and Montana’s Glacier National Park (reservations may be required) are a couple of highlights travelers hit before ending in Everett. This trip is best during the summer, when scenic places like the Great Lakes can be fully enjoyed.

3. U.S. Highway 50

• Start: Ocean City, Maryland
• End: Sacramento, California
• Distance: 3,019 miles

When Time Magazine published a story about the U.S. Highway 50 in July 1997, it noted the road’s duality, saying, “The road gossips down Main Street and dresses up for the cities and, when it reaches the desert, stretches to the horizon and falls fast asleep.” From Ocean City, Maryland, it travels through cities like Washington, D.C. and Cincinnati before ending in West Sacramento.

But it’s the more sparsely populated parts of the country that have become associated with this particular road. Nevada’s section of U.S. Highway 50, sporting lone landmarks like a tree draped with many shoes and mining towns like Eureka between miles of desert, was what Life Magazine called the “Loneliest Road in America” in the 1980s. While this drive is not for the fainthearted (there are only a few gas pumps between its endpoints in Ely and Fernley), it gives a sense of solace and quiet rarely found on the road nowadays.

4. U.S. Highway 61

Photo by Fotogro/Shutterstock

• Start: Wyoming, Minnesota
• End: New Orleans, Louisiana
• Distance: 1,407 miles

Bob Dylan wrote about his spiritual connection with U.S. Highway 61 in his memoir, stating that it “always felt like it was in my blood” as the road connected his birthplace in Duluth, Minnesota, through Mississippi Delta Country—the heart of the blues genre—to the music powerhouse city of New Orleans. (His love of the road has been immortalized in his 1965 album, Highway 61 Revisited.) While the highway now starts about 120 miles south of Duluth, in Wyoming, Minnesota, travelers on this road can still drive to New Orleans and find the birthplaces of artists who have been intrinsic to American music along the way: B.B. King, Johnny Cash, and Elvis Presley, to name a few.

It’s the blues genre that gave the road its nickname, the Mississippi Blues Trail. Explore this part of the road’s history by stopping at the Delta Blues Museum in Clarksdale and the Howlin’ Wolf Blues Museum in West Point. Much of Highway 61 is also a part of the Great River Road, a 3,000-mile series of state roads that parallel the full length of the Mississippi River. The road hugs the waterfront of river towns like Red Wing and Hastings in south Minnesota as well as natural areas like the Yazoo National Wildlife Refuge in Mississippi, offering scenic excursions on a journey rooted in the cultural history of the United States.

5. U.S. Route 1

Photo by Zoshua Colah/Unsplash

• Start: Key West, Florida
• End: Fort Kent, Maine
• Distance: 2,369 miles

Not to be confused with Highway 1 in California, U.S. Route 1 passes through the East Coast from Florida to Maine. Starting from “Marker 0” in the Keys, the road travels along Florida’s coast before heading inland through Georgia, the Carolinas, Virginia, and New Jersey. But once drivers hit Connecticut, the road snakes by the coast again—and eventually by Maine’s side of the U.S.-Canadian border—before stopping in the small border town of Fort Kent.

The journey covers many of the East Coast’s biggest cities, including Miami, Washington, D.C., and Boston. But it also does a good job of sandwiching other landscapes—like the small towns of the Southeast—in between the grand coastal stretches and urban hubs. Of course, if there’s a part you want to skip, there’s always I-95, the interstate that parallels the U.S. Route 1 from Miami to the Houlton–Woodstock Border Crossing in Maine.

6. U.S. Highway 80

• Start: Tybee Island, Georgia
• End: San Diego, California
• Distance: 2,734 miles

When the Automobile Club of Savannah created the Dixie Overland Highway in 1914, it created the outline for what would become U.S. Route 80. The drive goes through both the Southeast and Southwest regions, connecting Tybee Island, Georgia, to Southern California. The highway was wildly popular in the 1950s until various states started renaming parts of the road in the 1960s, turning pieces of the highway into different interstates.

Many portions of the highway are still considered important; states including Arizona have recognized parts of U.S. 80 as a historic route. The mostly forested, eastern portion—until Dallas, Texas—is the largest portion still intact, occasionally going by Deep South cities such as Macon, Georgia, and Montgomery, Alabama. Portions of the original road also exist west of Dallas, like New Mexico State Road 80 and Arizona State Route 80—but for the most part, drivers will need to follow a mix of I-8, I-10, and I-20 to re-create the path of U.S. 80. Nonetheless, the western half of the journey largely follows the red mesas and dry landscapes of the Southwestern region between cities such as El Paso and Phoenix before ending in Southern California.

7. Alaska for glaciers, photo safaris, and mushing lore

Photo by Patrick Federi/Unsplash

• Start: Anchorage
• End: Anchorage
• Distance: 954 miles

Alaska may be disconnected from the mainland states, but a drive across this vast expanse amounts to almost as many miles as a journey across the lower 48. Seeing snow-capped mountains, spectacular glaciers, and abundant wildlife from the deck of a cruise ship is unforgettable. But overland driving can be equally rewarding. This weeklong trip traverses four scenic byways and visits awe-inspiring sights like Denali, North America’s highest mountain peak.

Start on the two-lane Old Glenn Highway out of Anchorage, stopping to check out the Alaskan Native spirit houses and burial grounds at St. Nicholas Church and the Eklutna Historical Park in Chugiak. In Chitina, pick up a bush flight with Wrangell Mountain Air to remote McCarthy-Kennicott, the former mining town and its “sin city” sister deep in the vast Wrangell–St. Elias wilderness. (Hardcore road-trippers can drive the 60-mile McCarthy Road, though it’s slow going.) Stay the night at Ma Johnson’s Historical Hotel, a boardinghouse and bordello turned inn in McCarthy. Come morning, strap on a pair of crampons for a half-day Root Glacier trek with St. Elias Alpine Guides.

After flying or driving back to Chitina, head for Meier’s Lake Roadhouse in Gakona, a perfect pit stop along the dramatic Richardson Highway. The strawberry-rhubarb cobbler is tops. From Gakona, head northwest toward Denali National Park and Preserve for hiking, river rafting, and a meet-and-greet with the “canine rangers” at the Sled Dog Kennels. Don’t forget to try the fireweed ice cream at Shirley’s Northern Lights in Talkeetna before continuing on to Wasilla, home of the Iditarod Trail Sled Dog Race Headquarters.

For one last glorious look at Alaska’s untamed topography, book a flightseeing tour for your last day in Anchorage. The pilots at Rust’s Flying Service know these lands inside and out, and they’ll take you on a photo safari of the Knik or Triumvirate glaciers.