10 Road Trips You Can Take in a Week

We've planned 10 week-long road trips with routes, must-stops and where to stay along the way.  

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Glacier National Park, Montana to Jackson Hole, Wyoming

Start in Whitefish, a delightful ski town, before taking the impossibly scenic Going-to-the-Sun Road into Glacier National Park. Camp overnight or opt for the one-of-a-kind Sperry Chalet. (As long as you’re up for a 6.7-mile uphill hike and no hot water or showers.) The next day, stop for lunch in East Glacier Park village, then hop on 287 South for the state capital of Helena. Tuck into lunch at Steve’s Café, then continue south toward Bozeman and the Museum of the Rockies. A half hour south you’ll hit charming Livingston and its Old West vibe. Try Montana’s Rib & Chop House or Mark’s In & Out diner. Turn south toward Yellowstone and check into the all-inclusive Mountain Sky Guest Ranch. From here it’s on to Yellowstone. Take in Mount Washburn, the Grand Canyon of Yellowstone, Old Faithful and Mammoth Hot Springs (stick to the boardwalks; you can’t soak in these springs.) Make camp here before continuing on to Grand Teton National Park. Overnight at Dornans before concluding in Jackson Hole. Leave time to take in this posh ski resort, and recap your trip over dinner at Lotus or Rendezvous Bistro.

Chicago to Mackinac Island, Michigan

Mackinac Island feels stuck in the 19th century, but in a good way. From Chi-town, stick to Michigan’s Gold Coast, where you’ll find rolling hills, farm stands, sand dunes and vineyards. After crossing into Michigan, stop for lunch at Charlie's Piggin N' Grinnin' (the name alone) in Benton Harbor. Sated, keep chugging toward Holland, best known for its tulips. (This year’s Tulip Time Festival is May 6-14.) Visit Windmill Island Gardens, the Big Red Lighthouse and New Holland Brewing, then rest at Lake Ranch Resort. From here, Traverse City and its food scene beckons. Since the area’s known for tart cherries, stock up at Cherry Republic. Elsewhere, consider Cousin Jenny's Cornish Pasties and the food trucks at Little Fleet. Next, pull off an hour north in picturesque Charlevoix before overnighting in Mackinaw City, the gateway to Mackinac Island via a 20-minute ferry ride. You’ll have to leave your car at the ferry lot since Mackinac Island is car-free, but between bikes, electric scooters and horse-drawn carriages, you’ll hardly miss it.

 

Blue Ridge Parkway from Virginia to North Carolina

The Blue Ridge Parkway connects the National Parks of Shenandoah and Great Smoky Mountains, but it’s more than that. Thanks to 469 miles of spectacular scenery and clearly marked places to stop along the way, it’s made for road tripping. Start at the beginning of the route in Shenandoah National Park; Skyline Drive sets the tone. Stop for a stretch at the James River Visitor Center, then continue to the Peaks of Otter. Consider staying at the Peaks of Otter Lodge (it’s the only one on the Parkway open year-round). Hike to a pioneer cabin from the Smart View Picnic Area. Continue a short ways to the early 20th-century Mabry Mill and eat a hearty country lunch at the eponymous restaurant. As you cross into North Carolina, Moses H. Cone Memorial Park is popular for its Gilded Age estate. Take photos as the iconic Linn Cove Viaduct wends through the treetops, then pull off for Linville Falls, the Museum of North Carolina Minerals, Little Switzerland and the Folk Art Center. Take a slight detour into Asheville, then visit Biltmore Estate; spend the night in town. Back on the parkway, fit in Mt. Pisgah and Waterrock Knob before reaching the end of the line.

Pacific Coast Highway from San Francisco to Portland

Head north over the Golden Gate Bridge to experience the less crowded portion of the Pacific Coast Highway. Arrive early to Muir Woods to walk among the towering redwoods, stop to hike in Point Reyes National Seashore, then eat all the cheese at Cowgirl Creamery. Pull off in Bodega Bay for the views, then continue on to Mendocino and check into Sea Rock Inn. Dine at Trillium Café before settling in for the night. After breakfast, drive to Glass Beach near Fort Bragg to look for said sea glass. Redwood National and State Parks are next; pick a scenic drive and consider camping overnight. Keep heading up the coast to Prehistoric Gardens, an offbeat attraction with life-size dinosaurs (not to be confused with Jurassic Park). Grab a bite at Shark Bites Cafe in Coos Bay, then stay at Heceta Head Lighthouse or the Whale Cove Inn in Depoe Bay. Either way, go whale watching in Depoe Bay since it's considered Oregon’s whale-watching capital. Before turning off for Portland, it’s worth popping into Tillamook Cheese Factory for not just its cheese, but it’s two-dozen ice cream flavors.

New York City to Portland, Maine

Once you clear New York and lower Connecticut congestion, I-95 passes near picturesque coastal towns that become progressively more laid back. Drive past Greenwich, Stamford and Bridgeport before stopping in New Haven, home of Yale University. Tour the campus, then feast on pizza at Frank Pepe Pizzeria Napoletana. Continue to Mystic, Connecticut, made famous by the movie, before pulling into Newport, Rhode Island for a night or two at The Chanler at Cliff Walk. The following day, tour the Gilded Age summer homes, including The Breakers. Bypass Boston traffic for Newburyport, Massachusetts. Its cobblestone streets, charming shops and walkable downtown make it a worthy stop. Foodies shouldn’t pass Portsmouth, New Hampshire; dozens of options range from Portsmouth Brewery to The Friendly Toast. Cap off the day at the Captain Lord Mansion in Kennebunkport. Set out next for Portland Head Light, a historic lighthouse, before finally reaching Portland, Maine. Rejoice with celebratory oysters at Eventide Oyster Co.

Highway 61 (Blues Highway) from New Orleans to Nashville, Tennessee

Highway 61, also called the Blues Highway, is a historic stretch immortalized in song. It actually runs all the way to Chicago, but break it up to avoid pulling an Amazing Race. Start in New Orleans, and soak up jazz at Preservation Hall and The Spotted Cat Music Club. Venture into the Mississippi Delta and set out for Vicksburg; brush up on American history at Vicksburg National Military Park. Overnight here before making your way toward Clarksdale, Mississippi, considered the birthplace of the blues, but not before stopping for a thick milkshake at Chuck’s Dairy Bar in Rolling Fork, and visiting the Highway 61 Blues Museum in Leland. In Clarksdale, hit up Cat Head Delta Blues and Folk Art for all kinds of blues music. Catch live music at Ground Zero Blues Club, co-owned by Morgan Freeman, and Red's Lounge. If possible, time your trip for the Juke Joint Festival in April. Eat at Abe's Bar-B-Q, and experience sharecropper shacks by staying at the Shack Up Inn. Continue to Memphis for the Stax Museum of American Soul Music, Rum Boogie Café, Graceland and Central BBQ. Spend the rest of the trip in Nashville, where music highlights include the Country Music Hall of Fame, the Johnny Cash Museum, Robert’s Western World, Grimey’s New and Preloved Music, and of course, the Grand Ole Opry.

San Juan Skyway, Colorado

This 236-mile route passes through former mining towns in the San Juan Mountains, and is best done in summer when mountain roads are clear. Start in Ouray: Dubbed the Switzerland of Colorado, it also boasts five hot springs. Relax in the vapor cave at the Wiesbaden Hot Springs Spa & Lodgings; Ouray Hot Springs Pool will reopen to the public following a multimillion-dollar renovation. Navigating the Million Dollar Highway between Ouray and Silverton takes skill, since it involves numerous switchbacks and few guardrails, but you get breathtaking scenery in exchange. Once in Silverton, take the One Hundred Gold Mine Tour. Next up in Durango, channel Harry Potter by riding the Durango & Silverton Narrow Gauge Railroad, which is still steam powered. Grab a drink afterward at Steamworks Brewing Company. Rest at the historic Strater Hotel before striking out for Mesa Verde National Park, best known for its 600 ancient Pueblo cliff dwellings. Branch off and conclude in Telluride, one of the top spots in the country for skiing, but a must year-round. It’s also great for food, from Brown Dog Pizza to Allred’s Restaurant. Splurge and recharge at Lumière Telluride before heading home.

Pacific Coast Highway from San Francisco to Los Angeles

Miles of mountains and wild shoreline await on this part of the Pacific Coast Highway. Cruise along until reaching Santa Cruz and its boardwalk. After, drive another hour to Monterrey for the Monterey Bay Aquarium. Quaint Carmel-by-the-Sea is just a few minutes away; rest near the ocean at La Playa Carmel. From here you’ll encounter some of the best views of your life from the Bixby Creek Bridge. Continue to Julia Pfeiffer Burns State Park, or consider a mini-retreat at the nearby Esalen Institute. From here it’s on to Hearst Castle in San Simeon; don’t miss the elephant seals nearby. Further south, poke around town in Cayucos and hit up Brown Butter Cookie Company. San Luis Obispo is a short drive away; stay at the iconic Madonna Inn and explore this charming college town, including Mission San Luis Obispo de Tolosa and Bubblegum Alley. Pismo Beach is en route to Santa Barbara, a fantastic beach town. Overnight at the latter before setting out for Malibu, and then wrapping at the famed Santa Monica Pier.

Big Island, Hawaii

Unlike other Hawaiian islands, the Big Island offers everything from white- and black-sand beaches to active volcanoes. Start in Kailua-Kona, a great base for its beaches and shopping. Visit the historic Kailua Village, feast on fresh fish at Da Poke Shack, then head north to Kaloko-Honokohau National Historical Park. Continue along the black-sand beaches of the Kohala Coast to Mauna Kea Beach Hotel. Follow the coast to the beautiful Pololu Valley for hiking and more black-sand beaches. From here, turn inland along the scenic Kohala Mountain Road to the lush green hills of Waimea, where you can experience working ranches and go horseback riding. After, it’s a short drive to the flagship of acclaimed Merriman’s. Overnight in Waimea, then continue along the Hamakua Coast to Akaka Falls State Park. Spend a couple days in Hilo at The Palm Cliffs House Inn; wander downtown, visit Liliuokalani Gardens and shop at the farmer’s market. Set out for Hawaii Volcanoes National Park, then circle around the southern coast until reaching Kona Coffee Living History Farm. Back in Kailua-Kona, stuff yourself with malasadas (filled doughnuts) at Holy Donuts.

Route 66 from Albuquerque, New Mexico to Los Angeles

Route 66 stretches all the way to Chicago, but highlights in this section include curious roadside attractions, classic motels and all the kitsch you could want. After exploring Route 66 attractions in Albuquerque, strike out for Acoma Pueblo to learn about Native American traditions. Stop in Gallup, New Mexico to rest at El Rancho Hotel. You’ll soon cross into Arizona, the longest stretch of Route 66. Hike in Petrified Forest National Park and check out the Painted Desert Inn museum. Chow down at Joe and Aggie's Cafe in Holbrook, then check into the Wigwam Motel. (Yes, rooms are in wigwams.) Rested, keep on toward Flagstaff, then hit Seligman for Delgadillo’s Snow Cap Drive-In before spending the night at El Trovatore Motel. Continue to the former gold mining town of Oatman, where wild burros roam the streets. Pull off at the Mojave National Preserve, then stop at the preserved Roy's Motel and Café in Amboy, California. Eat up at Emma Jean's Holland Burger Café in Victorville, but save room for an egg cream at Fair Oaks Pharmacy and Soda Fountain in Pasadena. Celebrate your trip at the Santa Monica Pier, the literal end of the road for Route 66.

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