What better way to celebrate the beginning of summer than to hop in the car with the family or a dear friend and hit the road? Whether you’re on the hunt for the best lobster rolls in the land or the finest key lime pie, country charm or stately design, Old World elegance or modern panache, these are eight of the best East Coast road trips to take.
Maine: The lobster trail
- Distance: 232 miles
- Start: Ogunquit
- End: Acadia National Park
With 3,400 miles of coast, the Pine Tree State boasts one of the longest coastlines of any U.S. state and, as most Mainers will proudly tell you, the best lobsters in the world. Taste for yourself on this road trip, traveling Route 1, affectionately known as “the lobster trail,” along the storied, jagged coastline, stopping to sample lobster dishes in all forms—buttered, steamed, on a roll, or even in a decadent mac-and-cheese.
The trip starts in quaint Ogunquit, with its rare (for the area) three-and-a-half miles of white-sand beach. Make your first lobster of the journey count, steamed with a side of drawn butter at Barnacle Billy’s in picturesque Perkins Cove harbor. Stop at Big Daddy’s for a cone on your way to the shipbuilding center—and summer home of George H. W. Bush—Kennebunkport. Stay at the recently redesigned 150-year-old classic White Barn Inn, and consider a sailing trip for an afternoon. With lobsters cooked in ocean water, the legendary lobster roll at the Clam Shack is a must.
On your way to Portland, Cape Elizabeth is great for photos by the historic lighthouse, Portland Head Light, before fresh seafood with an ocean view at the Lobster Shack at Two Lights. Browse the cute shops and take a gallery walk in Portland before heading further up the coast to Georgetown (where freshly caught lobster meat is employed to tantalizing effect in the lobster roll at Five Islands) and Rockland (with a bustling arts scene on Main Street). Windsor Chairmakers sells exceptionally well-crafted furniture made from fine woods in Lincolnville. Finally, it’s time to get out of the car for a nice long stretch at trip’s end, Acadia National Park, where some 45 miles of bike trails beckon—a good way to work off those crustacean confections you’ve enjoyed on the way here.
Long Island’s Twin Forks: From country appeal to Hamptons elegance
- Distance: 45 miles (134 miles if starting from Manhattan)
- Start: Mattituck
- End: Montauk
Once you get past the horror of Long Island expressway traffic, you’ll quickly see why Manhattanites have been weekending along the coastal towns of the “twin forks” for generations. This trip begins on the North Fork, where you’ll wind along County Road 48 through country hamlets; pop into fine design shops and surprisingly wonderful wineries along the way.
In Mattituck, stop for insanely delicious treats from North Fork Doughnut Company, aka NoFo DoCo (trust us, try the Froot Loop one), and then feed the baby goats at Goodale Farms in nearby Riverhead. Further down the Fork, in Cutchogue, is one of the area’s finest wineries, Bedell Cellars, which hosts small group tastings; next up is the bustling (for the area) Greenport, alive with colorful artisan shops, galleries, and restaurants. Try the locally sourced watermelon spirit at sustainably-minded Matchbook Distilling Company—and consider a stay at the owner’s cute boutique hotel the Lin Beach House, before taking the ferry to picturesque Shelter Island, which features interior shops like Fredric Bernstein with its impossibly chic, punky decor. Take time for a kayak trip around the gentle waters, and try André Balazs’s Sunset Beach for a sophisticated cold beverage.
Ferry over to Sag Harbor on the South Fork, your gateway to the Hamptons, for lunch or dinner at the enchantingly warm Italian eatery Tutto il Giorno. (Co-owned by Donna Karan’s daughter, Gabby, it also sells tasteful decor items.) Stock up on sustainable beauty buys from Naomi Watts–backed Onda or Gwyneth Paltrow’s Goop, and browse more elegant home decor shops—Madison Street is packed with excellent choices (like Monc XIII). Accommodation options include the iconic American Hotel or the more luxurious Baker House 1650 in East Hampton for ultimate pampering. From here you can bike to Main Beach, one of the few legendarily scenic Hamptons beaches where you can also pay to park (during the week only). Or take a break from the sun and spend the afternoon basking in the magnificent gardens and outdoor sculptures at LongHouse Reserve while your Tesla charges right in the parking lot.
From there, head east to Montauk, stopping for a famed lobster roll at Bostwick’s Chowder House on Route 27 en route to Montauk. Hang 10 with the surfers at Ditch Plains, where you can grab lunch from the longtime food truck, the Ditch Witch, then browse the shops in town or pop into local favorite 668 the Gig Shack for its delicious blackened local fish “montacos” or tuna tartare taquitos. Consider a stay at the scene-y the Surf Lodge (if you want an entree to its wellness classes or concert series) or Gurney’s Montauk along old Montauk Highway, situated along one of the finest stretches of sand on the East Coast.
Florida’s Overseas Highway: Coastal glory + key lime pie
- Distance: 165 miles
- Start: Miami Beach
- End: Key West
Rent a convertible for this sun-kissed stretch: With 165 miles—113 of them on the iconic Overseas Highway (U.S. 1)—and 42 bridges to cross (including the spectacular Seven Mile Bridge, whose older span you can also walk over, in Marathon, FL), this American road trip is a classic. Electric vehicles can take you the whole way without a recharge stop—and there are multiple hotels and resorts with EV charging stations at trip’s end in Key West.
Begin in Miami, by strolling along the Wynwood Art District to snap Instagram stories in front of colorful street art murals, and visit the myriad groovy little galleries or the Museum of Graffiti and get a beer at any number of craft breweries. For an elevated sushi feast, book a 10-course chef’s tasting (or 6-course vegetarian menu) at the celebrated Austin import Uchi. The art deco hotels along Ocean Drive are worth a look before you head out of town. Put your top down and delight in the ocean air as you traverse U.S. 1, making stops along the way for key lime pie. You could make the entire trip a quest to find the perfect sweet/tart slice of heaven, but the best bite may be at trip’s end with the family recipe used at Key West’s Blonde Giraffe, a consistent fan favorite over the generations.
Full-fledged divers will want to spend an afternoon underwater in the Dive Capital of the World, Key Largo, which also boasts the first underwater preserve in the United States, John Pennekamp Coral Reef State Park. Everyone else can enjoy an afternoon of snorkeling along the coral reefs of the six Keys that make up Islamorada. (Geology and history buffs may want to check out Windley Key Fossil Reef Geological State Park and the History of Diving Museum.) It’s worth booking one of the 16 elegant suites at Casa Morada for a night or two to better savor every moment. At the tail end of the route, and the southernmost point in the country, Key West resides just 90 miles from Cuba and has an inclusive spirit that’s long welcomed LGBTQ communities and nourished writers such as Ernest Hemingway. Check in to the colonial Queen Anne Artist House, with rooms sporting 12-foot ceilings, and stroll through the historic district neighborhood.
Charleston to Savannah: A southern charmer
- Distance: 113 miles
- Start: Charleston, South Carolina
- End: Savannah, Georgia
Who couldn’t use some southern comfort on their travels? U.S. 17 connects two of the most iconic southern towns, from the foodie city of Charleston (from which you can also venture a bit further afield to the nearby sandy beaches of Sullivan Island) to the birthplace of southern Gothic, Savannah.
Beginning in Charleston, founded in 1670, history buffs will want to park at the elegant John Rutledge House Inn, built in 1763 for South Carolina’s first governor, who helped write the U.S. Constitution. For a more modern design, check in to the Restoration, and enjoy its notable photography installations and crab cakes at the rooftop eatery, the Watch. Or head to the aptly named Darling Oyster Bar for fresh seafood and seasonal cooking.
When you stroll along cobblestone streets to City Market, make time for at least one of the many historic plantations or gardens, such as the Gilded Age–era Calhoun Mansion and Gardens (now called the Williams Mansion), considered one of the most important pieces of Victorian architecture on the East Coast. A little over midway through the trip, stop in Beaufort, founded in 1711, for a scenic walking tour of historical sites and glimpses of Hollywood lore—parts of The Big Chill and Forest Gump were filmed here. Consider an overnight stay at the Beaufort Inn and an educational visit to Reconstruction Era National Historic Park and the Penn Center to better understand the history of slavery.
Heading on to Savannah—Georgia’s first city, founded in 1733—succumb to the Gothic charms (iron gates, massive, moss-covered oak trees) that have enchanted writers such as Flannery O’Connor and John Berendt. (You can tour the sites made famous from his book Midnight in the Garden of Good and Evil, such as the Mercer Williams House and the Bonaventure Cemetery.)
In Savannah, book a night at the luxurious Perry Lane Hotel and take your time wandering this many-storied city. The upstairs art galleries at City Market are worth browsing as are the eclectic boutiques (must-hit: the Paris Market) along Broughton Street. Dine on locally sourced creative fare like quail over grits cake and creole sauce from James Beard Award–winning chef Mashama Bailey’s the Grey (housed in an art deco gem, the city’s former bus stop). If you tack an additional 20 minutes onto your journey, you can check out laid-back Tybee Island with its tiny cottages, five miles of tidal beaches, and the tallest lighthouse in Georgia.
Blue Ridge Parkway: Scenery that commands you to slow down
- Distance: 384 miles
- Start: Charlottesville, Virginia
- End: Asheville, North Carolina
Slow it down and take in the memorable scenery on this bucolic trip. This favorite stretch of the 469-mile-long Blue Ridge Parkway, which takes you from Shenandoah National Park over the Blue Ridge chain to the Great Smoky Mountains, offers unparalleled vistas and natural highs, plus a multitude of cultural charms. Book a night at the 35-room Oakhurst Inn in Charlottesville, and take time to visit Thomas Jefferson’s Monticello before embarking on the journey. There are opportunities to hike along the Appalachian Trail or go fly-fishing at the Tye River before replenishing with a country ham sandwich at Layne’s Country Store in Glasgow. And just a 15-minute detour from the Parkway is the impressive limestone arch of the National Historical Landmark Natural Bridge, or “Nature’s Cathedral.”
An afternoon in Roanoke, an hour away, brings you the contemporary and folk art delights of the Taubman Museum of Art, and the farm-to-table fare of the River and Rail Restaurant. Get your bluegrass fix afterward at Floyd Country Store. Further up the road, you’ll find the sights and sounds of rural Appalachia at Mabry Mill; Sunday afternoons are made for hootenannies here. Stay overnight in a luxury tree-house cottage or romantic log cabin at Primland, which offers an observatory for stargazing.
Keep the tunes a-comin’ with a stop at the Blue Ridge Music Center, where string bands knock out bluegrass music daily. Wind around spectacular curves as you cross the North Carolina border. The Parkway Craft Center outside Blowing Rock offers the chance to get crafts, with the Southern Highland Craft Guild hosting demonstrations by artisans on the porch of the Moses Cone Manor. In Asheville, you can tour the fabled Biltmore Estate (stay over at one of three on-premises hotels), browse the Mast General Store downtown, and cap things off with a hearty meal at the community-driven Rhubarb and a craft beer from among the 48 companies that brew here.
Check out AFAR’s favorite Blue Ridge Mountain cabins to rent on Airbnb and VRBO.
From NYC to Woodstock: An upstate sojourn
- Distance: 142 miles
- Start: Manhattan
- End: Woodstock
Yes, New York City is one of the great cultural centers of the world. But there’s a world of art and culinary treasures just outside the city that’s worth exploring as well, not to mention scenic mountain ranges and preserves. Cross the GW Bridge and take the leafy Palisades Parkway, which hugs the Hudson River, up toward Storm King Art Center for an afternoon of awe-inspiring large-scale outdoor art sculptures. From here, travel another 22 miles north, crossing back over the Hudson River (via I-84 North), and check in to the industrial-chic Roundhouse in Beacon, housed in an old textile factory and offering romantic views of the waterfall that feeds into Fishkill Creek. There’s a creative restaurant on premises, and Dogwood Bar & Restaurant down the street offers craft cocktails (like the hot and smoky Dogwoodrita).
Here you can spend the next morning viewing the impressive collection at Dia Beacon (the Dan Flavin installations are worth the trip alone) before crossing back over the bridge and taking 87 to 299 W to get to Mohonk Mountain House. Spend a night or two soaking up the Old-World rustic feel and immersing in nature: You could canoe in the pond, hike the magnificent property, or rock climb the Shawangunk Mountains in nearby Mohonk Preserve. Take a drive through adorable towns like Rosendale and High Falls, where you’ll find upscale design shops like Object Found on your way to Kingston, which has become a bit like Brooklyn North. Browse shops and dine at Kingston’s first zero-waste restaurant and cocktail bar, Miss Bāo.
Wrap things up a short 11-mile drive further upstate in Woodstock, which still retains its bohemian charm all these years later. (Go on, cut loose, and free-form dance to drum circles with the tie-dyed set in the town square in the evening.) It also boasts fine dining (like Cucina), tastefully curated boutiques, and a killer bookshop, the Golden Notebook. For a quirky stay, consider the Herwood Inn, with four suites paying homage to female music icons. Rock on!
North Carolina’s Piedmont Region: A reinvented core
- Distance: 185 miles
- Start: Raleigh
- End: Charlotte
North Carolina gets a lot of fame for its beaches on the east and the Blue Ridge mountains on the west, and now its previously unsung Piedmont region is garnering attention for road-trip wanderers. In the words of AFAR writer Sheryl Nance-Nash, the Piedmont’s “former textile mills and tobacco warehouses are being transformed into innovation hubs and food halls, and many people have flocked to the area to live.”
Start your trip through the reinvented region in Raleigh, North Carolina, Nance-Nash suggests, where you can spend your time admiring art installations, murals, and museums like the North Carolina Museum of Art and CAM Raleigh. While you’re here, stay in historical accommodations like the Heights House Hotel, an 1858 Italiante-style mansion in downtown Raleigh.
Next: Drive 80 miles west to Greensboro, a city rife with southern history. The perfect place to start your tour is with the International Civil Rights Center & Museum at the F.W. Woolworth building, where four college freshmen helped launch the sit-in movement in 1960—the museum even displays a restored lunch counter, preserved in the original location of where the momentous event took place. Then, have Sunday brunch at Magnolia House, where such legends as James Brown, Ray Charles, and Tina Turner have stayed.
A mere 30-minute drive is the small and artistic city of Winston-Salem. Have a meal at Sweet Potatoes, a homey joint cofounded by James Beard–nominated chef Stephanie Tyson, before walking off your food baby in the city’s Downtown Arts District. The area hosts a cluster of murals, galleries, boutiques, breweries, and distilleries, and the monthly First Friday gallery hop nights are a must-experience event.
Finally, end your trip by the South Carolina border in Charlotte. See the Queen City’s fast growth up close through its sprawl of neighborhoods—one of them being NoDa, an arts and entertainment district known for street art, creative people, and colorful establishments. Here you can find vintage clothing at the Rat’s Nest, or relax at Smelly Cat Coffee House & Roastery. When it comes to cuisine, restaurants like Midnight Diner, Leah & Louise, What the Fries, and Mert’s Heart & Soul will fill your body with southern-fried goodness. End things with a beer at the Olde Mecklenburg Brewery—the city’s oldest—or with a dessert at one of the Amelie’s French Bakery locations.
Northwest Florida: A postcard-worthy stretch of Mexico’s Gulf
- Distance: 28.5 miles
- Start: Inlet Beach
- End: Topsail Hill Preserve State Park
“If Miami’s love language is spicy, then northwest Florida’s comes through in a syrupy coo,” writes AFAR’s Terry Ward about the upper section of Florida that hugs the Gulf of Mexico. Scenic Highway 30, a nearly 30-mile offshoot of U.S. Highway 98 that runs through Walton County, whisks you to the seaside towns and white-sand beaches that give this area its dreamy vacation reputation.
Start your journey at Inlet Beach, and take your time exploring the residential Gulf-front community Rosemary Beach and the new urbanism architecture of Alys Beach, Ward recommends. The sun-kissed fun continues when you head 10 miles east to Grayton Beach and visit Grayton Beach State Park (which has been praised as one of the most beautiful beaches in the country). For lunch, go to Grayton Beer Co. for its shrimp po’boys or the Red Bar—a lunch and dinner spot beloved for its crab cakes and wall-to-ceiling collection of eclectic decorations.
Drive about five miles west and wind down your day trip by visiting Topsail Hill Preserve State Park’s 25-foot dunes and coastal dune lakes, which are lakes with both fresh and saltwater that exist in dune ecosystems. (Such lakes can only be found in Madagascar, New Zealand, Australia, and a small number of other places outside of the area.)
Choose to rest your head from a variety of stays along this route: There’s the WaterColor Inn in Santa Rosa Beach, which stands between the Gulf and Western Lake, and the Pearl Hotel at Rosemary Beach, with turrets and a clock tower that bring a sophisticated twist to the getaway establishment.
This piece was originally published on June 7, 2021, and was updated in May 2022, with new trips in Florida and North Carolina by Chloe Arrojado.
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