10 Road Trips You Can Take Over a Weekend

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

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Miami to Key West, Florida

This stretch of US 1, commonly known as the Overseas Highway, is only 113 miles, but there are plenty of reasons — from roadside souvenir shops to seafood shacks — to stop along the way. Once you enter the Upper Keys, refuel at Alabama Jack’s or Mrs. Mac’s Kitchen in Key Largo. Scuba divers will love John Pennekamp Coral Reef State Park, which contains the only living coral reef in the U.S. (and an underwater park). Divers can also overnight at Jules Undersea Lodge, which claims to be the only underwater hotel in the world. Or spend the night at halfway point Islamadora in the Middle Keys. Options include Casa Morada or the family-friendly Hawks Cay Resort. Lazy Days Restaurant is a popular eatery, while feeding tarpon at Robbie’s is another popular pastime. Continue down to Marathon for the Dolphin Research Center and Turtle Hospital. Grab a bite at the quirky Wooden Spoon, and leave time for Instagram opps along the iconic Seven Mile Bridge into the Lower Keys. From here, it remains a straight shoot into Key West.

New York City to the Catskill Mountains

The Palisades Parkway and Taconic Parkway are among the scenic routes to the Catskills, a diverse, woodsy region that’s evolved from its ‘50s stereotype of summer resorts. Your first stop should be Woodbury Common Premium Outlets, just an hour north of the city, for discounts on high-end brands. Further north, make time for charming Hudson Valley towns such as Poughkeepsie and Rhinebeck. Book reservations in advance to dine at The Culinary Institute of America in Hyde Park after you’ve visited the nearby Vanderbilt Mansion National Historic Site. If it’s in your budget, spring for the fairy tale-esque Mohonk Mountain House in New Paltz. Meander north into the Catskills to hit artsy Woodstock (ironically, the eponymous music fest wasn’t held here, but some 50 miles west in Bethel). Stay at the cozy Woodstock Inn on the Millstream, catch a live performance at Levon Helm Studios, and go vegan at the Garden Café. Head northwest for Table on Ten in rural Bloomville, a down-home destination for farm-to-table goodness. Afterward, bed down in one of its three bedrooms. Leave time to wander quaint Delhi, then travel south along the name-says-it-all Upper Delaware Scenic Byway before heading back home.

San Francisco to San Simeon, California

The Pacific Coast Highway appears on road trip lists for good reason — stunning views but frequent closures so be sure to check road availability before you travel. The windy road hugs the rugged coast for much of this route, with breathtaking views between Monterey and the Big Sur region. Stop in Half Moon Bay for stunning beaches, and keep your eyes peeled for whales. Overnight at The Ritz-Carlton and see unbeatable views from an oceanside cliff. Continue south to Santa Cruz for a stroll on the boardwalk before motoring toward Monterey. En route, stop for grub at the eclectic Whole Enchilada in Moss Landing. Keep an eye out for farm stands selling artichokes; Castroville is considered the artichoke capital of the world. In Monterey, check out Fisherman’s Wharf and the acclaimed Monterey Bay Aquarium. Explore charming boutiques at nearby Carmel-by-the-Sea. (Fun fact: Clint Eastwood was a former mayor.) Or hike in Point Lobos State Park before driving over the iconic Bixby Creek Bridge. Decompress at award-winning Post Ranch Inn; just past it is Nepenthe for drinks and views. Cap off your trip by touring the legendary Hearst Castle in San Simeon.

Chicago to Lake Geneva, Wisconsin

This resort town is where Gilded Age families with names like Wrigley had summer homes. Head north along Lake Michigan to Highland Park, where the Ravinia Festival holds outdoor concerts every summer. From here, turn west for handcrafted chocolate at Ethereal Confections in Woodstock. Once you cross the state line, catch a show at The Dancing Horses Theatre. As the name implies, this is an equestrian show where entertainers perform elaborate feats on festooned horses. Once in Lake Geneva, hike part of the 26-mile Lake Geneva Shore Path and ogle at the former summer estates of the wealthy. After working up an appetite, Popeye’s is a local institution for rotisserie chicken (not to be confused with the fast-food chain). Stay at The Baker House to channel the Gilded Age era. Astronomy buffs should make an excursion to Yerkes Observatory, while train lovers can ride the East Troy Electric Railroad, a remaining holdover of original electric lines.

Austin to Fredericksburg, Texas

Wine-centric Fredericksburg in Texas Hill Country is a straight shot on 290, or a bit further along scenic US-281. If you choose the former, your first stop should be in bucolic Dripping Springs for Rolling In Thyme & Dough. If you’re hankering for barbeque, detour to The Salt Lick in Driftwood. Continue on to Johnson City (President Lyndon B. Johnson’s hometown), for Pedernales Falls State Park for swimming and camping. Once in Fredericksburg, base yourself at Magnolia House and hit the wine road for some of the dozens of wineries in the area. If beer’s more your thing, don’t miss Fredericksburg Brewing Company. Since Fredericksburg’s German past is still very present, experience it at Old German Bakery & Restaurant. Make a side trip to famed old-school dance hall Luckenbach to practice your two-step. If visiting in April, no Hill Country road trip is complete without driving past the famous wildflowers and bluebonnets that blanket the area.

Boston to Portland, Maine

From Boston, focus on the coastal towns, starting in Salem to learn about the witch trials. Meander north along the coast to Manchester-by-the-Sea, popularized by the movie, for its harbor and small-town charm. Further north, stop in Newburyport for shopping and enjoy dinner at the top of Newburyport Lighthouse before checking into the Compass Rose Inn. The next day, set off for the foodie haven of Portsmouth, New Hampshire for Black Trumpet Bistro, Caffe Kilim and more. Make time to visit Kennebunkport for a special dinner at the White Barn Inn Restaurant, then roll into Portland, another major foodie city. It’s more than just lobster rolls, but eat those too. In fact, you’ll find some of the best at the non-descript Fishermen’s Grill. Don’t leave before trying Duckfat, Central Provisions, Holy Donut (made with Maine potatoes) and Eventide Oyster Co. The craft beer scene is also strong; favorites include Allagash and Bissell Brothers. On your way home, swing into Scarborough to say hi to Lenny, billed as the only life-size chocolate moose in the world.

Seattle to San Juan Islands, Washington

The remote San Juan Islands provide ideal Pacific Northwest vistas (think rugged landscapes peppered with Douglas firs) and a slower pace. While there are actually 172 islands, ferries only serve San Juan, Orcas, Lopez and Shaw. It’s an easy 90-minute drive up I-5N to the ferry crossing at Anacortes; luckily road trippers can bring cars onboard, but reserve ahead since many others have the same idea. Grab a bite beforehand at Gere-a-Deli before setting sail for Friday Harbor, considered the entry point into the islands. Fear not though, as this historic seaport has managed to retain its authentic appeal. Stay in town and poke into independent booksellers and jewelry shops, or hit the road to visit alpacas at Krystal Acres and wander lavender fields at Pelindaba Lavender Farm. Take the scenic byway route to Roche Harbor and overnight at the Roche Harbor Resort. On your way back, pop into San Juan Vineyards. Don’t leave before taking a whale-watching excursion to spot the famous orcas.

Los Angeles to Palm Springs

Palm Springs is experiencing a resurgence in popularity thanks to trendy new hotels and restaurants. However, much of the area’s appeal resides beyond this scene. Once you get out of dodge, follow Interstate 10 until you reach the Desert Hills Premium Outlets for designer discounts. Back on the road, pull off at Hadley Fruit Orchards for a date shake, then marvel at the wonderful weirdness of the Cabazon Dinosaurs. (You might remember them from Pee-wee’s Big Adventure.) From here, detour 10 minutes north to the San Gorgonio Pass Wind Farm, a collection of wind turbines that generate energy. Once in Palm Springs proper, ride the Palm Springs Aerial Tramway, which slowly rotates as it ascends to 8,516 feet. Base yourself at the recently renovated L’Horizon Resort & Spa to visit Indian Canyons and Joshua Tree National Park, and learn about wildlife and desert conservation at the Living Desert Zoo and Gardens. Nearby, College of the Desert Street Fair is a long-running weekend flea market where you can find everything from turquoise jewelry to Hawaiian shaved ice. And you can’t go wrong with baby back ribs and microbrews at Babe's Bar-B-Que & Brewhouse in Rancho Mirage.

Jackson Hole, Wyoming to Yellowstone National Park

This is true of all road trips, but be sure to map out your route in advance as some roads, restaurants and hotels close during the winter, which can last through mid-April. Regardless of when you travel, majestic skies and backcountry terrain await, starting in Jackson Hole. Before heading to Grand Teton National Park, fuel up at the Chuckwagon at Dornans. Rib-sticking fare includes sourdough pancakes and biscuits in sausage gravy. Spend the day driving around Grand Teton, from Teton Park Road to Colter Bay Village before settling into a cabin at Signal Mountain Lodge. After a restful sleep, strike out for Yellowstone National Park. Once in the park, must visits include Old Faithful, Mammoth Hot Springs, Mount Washburn and the Grand Canyon of Yellowstone. Camping options abound or turn in at the landmark Old Faithful Inn.

Washington, D.C. to St. Michaels, Maryland

The historic seaside village of St. Michaels was a shipbuilding port in Colonial times; more recently, Wedding Crashers was filmed here. After clearing D.C. traffic, continue on 50 East until reaching the state capital of Annapolis. Visit the U.S. Naval Academy, or head over to Ego Alley to watch boats and explore shops and restaurants. As it’s on Chesapeake Bay, go for seafood, whether it’s Mason’s Famous Lobster Rolls, Wild Country Seafood or Cantler’s Riverside Inn. Cross over to Kent Island to compare Blackwater Distilling and White Tiger Distillery, or take a factory tour at Paul Reed Smith Guitars. Head into St. Michaels to collapse at the Inn at Perry Cabin by Belmond. In town wander the historic streets and explore the Chesapeake Bay Maritime Museum. Drive to nearby Tilghman Island for kayaking, fishing and sailing, and stock up on food supplies at the Tilghman Island Country Store.

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10 Road Trips You Can Take Over a Weekend

Related To:

Shop This Look

Miami to Key West, Florida

New York City to the Catskill Mountains

San Francisco to San Simeon, California

Chicago to Lake Geneva, Wisconsin

Austin to Fredericksburg, Texas

Boston to Portland, Maine

Seattle to San Juan Islands, Washington

Los Angeles to Palm Springs

Jackson Hole, Wyoming to Yellowstone National Park

Washington, D.C. to St. Michaels, Maryland

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