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.
Photo By: KenWiedemann
Photo By: Michael Marquand
Photo By: Ian Cumming
Photo By: csfotoimages
Photo By: tomwachs
Photo By: DenisTangneyJr
Photo By: LoweStock
Photo By: Stephanie Sawyer
Photo By: lightpix
Photo By: SeanPavonePhoto
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
San Francisco to San Simeon, California
Chicago to Lake Geneva, Wisconsin
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
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.