The Best East Coast Road Trips for Every Season
People talk a big game about driving up and down the West Coast, and that’s all well and good—and perfectly deserved. However, the East Coast's road trip opportunities are ready and waiting to be explored, and are a bit underrated, if you ask me. Sure, it lacks the sprawl of the middle and west of the country with its large plains and arid Southwest, but with 14 states, four distinct seasons (beyond Florida’s endless summer, that is), and an incredibly diverse range of cultures and landscapes, the East Coast really is the coast with the most—and the only possible way to sample its infinite variety is on the road. Here are 12 of the best East Coast road trip itineraries, including where to stop, where to stay, and what to eat along the drive.
This gallery has been updated with new information since its original publish date.
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Courtesy The Chanler at Cliff WalkSmall but mighty: New Haven to Newport
Hit the highlights of two of America’s smallest states, Connecticut (#3) and Rhode Island (#1) with the 100-mile drive along US-1 from New Haven, Connecticut, to Newport, Rhode Island. This journey is a cinch for Bostonians and New Yorkers alike, and is chock-full of underrated pizza spots, scenic cliffs, and, of course, historic mansions. Anticipate the best views along oceanfront Scenic Route 1A in Rhode Island from Westerly to Wickford (At 39.6 miles, that’s a long distance in Rhode Island terms.)
Where to stop: When you stop in Newport, head to the cliff walk, a light and breezy 3.5-mile hike with panoramic bay views and sights of the Vanderbilt estate known as the Breakers, among other Gilded Age mansions. Experience a different side of the Breakers on a “Servant Life Tour,” which exposes the back-of-house operations that fueled socialite events at the 65,000 square-foot mansion designed by architect Richard Morris Hunt.
Where to eat: Fuel up at the start of your journey in New Haven with the famed clam pie at Frank Pepe’s pizzeria (as featured on Ugly Delicious among many other hit shows). The accolade-racking pie is well worth the wait.
Where to stay: If you’re itching to splash out, look no further than The Chanler at Cliff Walk in Newport, which has landed on our Readers' Choice Awards a whopping seven times. We’re partial to the Martha’s Vineyard villa, with its ocean view and canopied four-poster king bed.
Chase Baker/UnsplashTropical temptations: Miami to Key West
Florida’s Overseas Highway is a 107-mile highway that connects the southernmost reaches of Miami, near Everglades National Park, to the southernmost point of the continental United States in Key West. It’s about a four-hour drive across countless coral and limestone islets on a two-lane highway, so use the slow-moving traffic as an excuse to stop to sightsee, eat, snorkel, or swim. After crossing the long and narrow seven-mile bridge, look forward to the most beautiful—and famous—parts of the Florida Keys, including Bahia Honda State Park and the self-proclaimed Conch Republic (aka Key West).
Where to stop: Swim among Technicolor tropical fish at either John Pennekamp State Park in Key Largo or Sombrero Reef off Marathon in the Middle Keys. Organized snorkeling tours are available at both. Also get some beach time at Bahia Honda State Park. Sitting at the confluence of the Atlantic Ocean and the Gulf of Mexico at mile marker 37 of US-1/Overseas Highway, this 524-acre beach park has some of the finest stretches of sand in the Florida Keys. There are both secluded and more trafficked spots for sunbathing and excellent photo opps of the largest intact section of Henry Flagler’s elevated overseas railroad.
Where to eat: Where Miami ends and the Overseas Highway begins, there’s an option for taking a secondary road, Card Sound Road, to initially reach the Upper Keys (you’ll then connect to the Overseas Highway). Take the Card Sound detour, and stop for lunch at Alabama Jacks, a waterfront dive bar and eatery with the best conch fritters and mahi mahi sandwiches in the Keys. If opting for the entirety of the Overseas Highway, stop for lunch at Mrs. Mac’s Kitchen, ordering the catch of the day (usually snapper) and an obligatory slice of key lime pie (note: they have whole pies available to-go).
Where to stay: Spend the night relaxing at The Reach Key West, Curio Collection by Hilton, located on a quiet stretch of beach but just a short walk from the bustle of central Key West.
Courtesy Fairmont Copley PlazaAn urban adventure: Boston to NYC to Washington, DC
For first-timers visiting the northeast from elsewhere in the country, or even from outside of it, experiencing these three iconic and historic cities is a necessity. This classic itinerary hugs the coast, breezing through Rhode Island and Connecticut past harbors, marshes, and the Atlantic Ocean before you skate past the Big Apple skyline. The beauty of this journey is that you can ditch your car and travel by train—all three cities are on Amtrak’s Northeast Regional and Acela Express routes. It’s one of America’s few urban pipelines that’s nearly as well-serviced by trains as Europe. Tack more cities onto the journey, or make a swap if you’d like—the Northeast Regional also makes stops in Providence, Rhode Island; Philadelphia; and Baltimore; among many others.
Where to stop: If you have limited time in each of these cities, you can’t go wrong with the following classic activities. In Boston, attend a Red Sox game at vibrant and energetic Fenway Park (or another sporting event, as seasons dictate). In New York, enjoy the Upper East Side with a visit to the Metropolitan Museum of Art, followed by a stroll in Central Park next door, capping the evening off with a drink at the Carlyle’s Bemelmans Bar. In DC, stroll the National Mall and visit the Air and Space Museum. These cities are universes unto themselves, and these are just a few ideas to get your itinerary started. To do more research on what they each have to offer, check out our official Boston, NYC, and Washington, DC, travel guides.
Where to eat: In Boston, where you’ll find some of the freshest seafood around, you can’t go wrong with a lobster roll from Neptune Oyster, which won Boston magazine’s 2023 best lobster roll award. While you’re in the North End, snatch up some cannolis from Mike’s Pastry. In New York, where the culinary options are almost more overwhelming than anywhere else on Earth, consider getting lost in Chinatown, where you can opt for something affordable yet delicious—like dim sum at Nom Wah Tea Parlor—or something elevated and special, like family dinner at Hwa Yuan Szechuan. In DC, Ben’s Chili Bowl is a must-visit stop, a landmark institution famous for its half-smokes, a local delicacy involving half-beef, half-pork smoked sausage covered in chili. For more ideas, explore our Boston, NYC, and Washington, DC, restaurant guides.
Where to stay: Kick off the trip with a stay at Boston’s timeless Fairmont Copley Plaza. The historic hotel, a repeat-Readers’ Choice Awards winner, has stood next to Boston Public Library since 1912, and has the elegance of old-time Boston, but with all of the modern amenities you'll need. For detailed, on-the-ground hotel intel, read Condé Nast Traveler’s Boston, NYC, and Washington, DC, guides to the best hotels.
Brian Samuels/Fox & The KnifeMass magic: Salem to Provincetown
Massachusetts is rife with personality-filled towns and cities, the best of which lie off the 135 miles of highway connecting spooky Salem and the colorful tip of Cape Cod, Provincetown. On the mainland, expect plenty of historical sites, important monuments, and major universities while the curling bicep of Cape Cod via U.S. Route 6 promises riveting marine experiences and a restorative salty breeze, ending in the impossibly fun LGBTQ+ Mecca of Provincetown.
Where to stop: Let Salem cast a spell on you. The city’s prolific 18th century facades now house the likes of cool coffee shops, pop-up shops, galleries, and boutique hotels. Next, experience a different side of Cape Cod through a once-in-a-lifetime research expedition with Atlantic White Shark Conservancy (AWSC), conducting great white shark research off the southern cape near Chatham. Just south of Provincetown, pop into Truro Vineyards + South Hollow Spirits, which is both a winery and a distillery that makes gin and rum. Once in Provincetown, explore the uninhabited sand dunes of the northern Cape with Art’s Dune Tours or set sail on a highly rewarding whale watch with eco-conscious company Dolphin Fleet.
Where to eat: Experience Boston’s foodie renaissance at restaurants like Coquette, Wood Hills Pier 4, and Fox & The Knife. For a fancy Cape classic, dine at the Chatham Bars Inn restaurant. The waterfront dining is on Chatham Harbor, offering those much-needed views and the premium quality seafood to match. The New England clam chowder is legendary.
Where to stay: In Provincetown, settle into AWOL, a seasonal 30-key inn by Lark Hotels, located within walking distance of both Herring Cove Beach and the town’s principal thoroughfare.
Gary W. Kellner/The Lodge at Spruce PeakGiving it 100: Vermont Route 100
Spanning more than 200 miles of idyllic New England countryside and almost the entire length of Vermont, this route takes you through countless Norman Rockwell-esque towns. Pass country stores and farm stands and explore the well-traversed stops of Wilmington, Ludlow, Killington, Warren, and Stowe.
Where to stop: In Weston, browse around the Vermont Country Store (est. 1946) where you’ll find everything from old-fashioned fudge to seersucker pajamas. In Brookfield, stock up traditional goat milk’s caramel sauce at the family-run Fat Toad Farm and watch the crew making the good stuff on this working farm (There are no tours per se but you can observe the process during daylight hours most Mondays-Thursdays). Take the time to drive slowly—and stop often—to take in the natural splendor between the mountain ridges of Stowe and Waterbury on the 14-mile Green Mountain Byway (a jazzed-up name for this highly scenic stretch of VT Route 100).
Where to eat: You can get casual authentic Mexican eats at an outpost of the no-frills, Vermont favorite Mad Taco in Waitsfield. In Stowe, dine at Plate, a small and stylish family-owned restaurant that showcases the best of Vermont’s farm-to-table riches and offers incredible vegetarian and vegan options (the veggie burger and vegan “crab cakes” are equally epic).
Where to stay: In Stowe, take in New England’s all seasons outdoor pursuits at the family-friendly (four-legged members included) Lodge at Spruce Peak. Depending on the time of year, pursuits such as hiking, skiing, mountain biking, ice climbing, and canoeing may be on offer. There are also concert series, specialty dining events, movies under the stars and seasonal installations (such as an ice-skating rink in winter), all taking place in the Spruce Peak Village next to the lodge.
Don Riddle/Courtesy Four SeasonsJust magical: Savannah, Georgia, to Orlando, Florida
Head from one dreamy southern city to another with a 280-mile road trip between Savannah and Orlando. From Savannah’s charming Spanish moss and pastel mansions to Orlando’s joyful amusement parks, this trip feels like a ream of pages torn from a storybook.
Where to stop: Stop along the way in Spanish-influenced St. Augustine, Florida—founded in 1565, it’s one of America’s oldest cities—and pay a visit to the Castillo de San Marcos National Monument, a 17th-century Spanish fortress on the waterfront. Enjoy a drink with sunset views at the Reef. If you’re a theme park person, it’s worth checking out Orlando’s many amusement parks, like Walt Disney World or Universal Studios. In Savannah, spend your time taking in the impressive architecture, walking through the historic district, and enjoying the picturesque parks.
Where to eat: In Savannah, first-time visitors should dine at the Olde Pink House Restaurant, a classic. The restaurant and tavern serves food in a 1771 mansion, and is known for the piano bar downstairs. Must-orders include the flounder and shrimp and grits.
Where to stay: Culminate the journey with a stay at the Four Seasons Resort Orlando, a 2023 Readers’ Choice Awards winner. The resort combines luxury with a cozy, kid-friendly design. Highlights include a waterpark for the kids, an adult-only pool for everyone else, and a Michelin-starred rooftop steakhouse restaurant with fireworks views. For Savannah picks, take a look at our favorite hotels in the area.
- Jane Khomi/Getty
City lights to big falls: New York City to Niagara Falls
The East Coast as a whole is a marvel, but New York State is worthy of its own dedicated exploration. New York is sprawling and expansive in its qualities—from one of the world’s best cities, to the Hudson River Valley, to the Adirondacks, to the sparkling Finger Lakes, to Niagara Falls. To drive top to bottom through this diverse state, we recommend starting in NYC and ending at the falls.
Where to stop: The scenic route travels up I-87 through the Hudson River Valley, veering west through Cooperstown, before you make your way to I-90 and ride it the remainder of the way to the falls.
Ideal stops along the way include Catskill, New York; the baseball hall of fame in Cooperstown; and a detour from Syracuse to one of the Finger Lakes, such as Skaneateles.
Where to eat: In the hamlet of Catskill’s Leeds, New York, of all places, dine at one of the best Mexican restaurants in the state, Casa Susanna, which has earned accolades from the critics at Eater and Esquire. Helmed by chef Efrén Hernández and serving the interior Mexican cuisine with a focus on the flavors of Jalisco, the restaurant makes all of its own tortillas in-house and the wine list features rare low-intervention wines from Mexico. Casa Susanna is on-site at the new hotel-cabin concept, Camptown. For NYC eats, check out some of our top restaurants in the city.
Where to stay: In Catskill, stay at aforementioned Camptown, a property full of gussied-up, colorful cabins that guests get all to themselves—there are working fireplaces and everything—as well as a motor lodge with additional accommodations. (Read a full review of the property here.) Once you make your way further upstate, book a stay at Otesaga Resort Hotel in Cooperstown—a five-time Readers’ Choice Awards winner since 2017—a sumptuous and historic hotel that feels out of the past, located on a gorgeous, isolated lake.
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Quintessential coastal charm: Portsmouth, New Hampshire to Bar Harbor, Maine
There’s nothing like an extended northern New England coastal drive, dotted with impossibly quaint seaside villages. From Portsmouth, New Hampshire, and all the way up the coast of Maine, roll past endless beaches and fishing harbors, artists’ colonies and historic districts.
Where to stop: Plan to spend a few mealtimes in Portland. Though Maine's is the smaller and lesser-hyped Portland, it’s become a hot foodie city where lots of young chefs—alumni of bold restaurants in New York—have gone to open their own first spots. Further north near Bar Harbor, plan a day in Acadia National Park. Take the 27-mile Park Loop Road, which curves along the boulder-strewn coastline, through dense deciduous forest, and passes sights like the iconic Cadillac Mountain. For more intimate experiences with Acadia, detour on to unpaved roads; or better yet, park the car for a bit and cycle, hike, or venture on horseback on the myriad, carless “carriage roads” that zigzag through the heart of the park. Also, make sure to hit Sand Beach, the only non-rocky beach in the park and arguably Maine’s most stunning swathe.
Where to eat: Besides all the great restaurants in Portland, treat yourself to briny local oysters and local seafood delights at Row 34 Portsmouth. In Camden, indulge in a creative, five-course, wine-paired lobster-tasting menu at award-winning Natalie’s Restaurant.
Where to stay: At one end, check into the cozy Hotel Portsmouth, which screams Americana by design and is within walking distance to the town’s prolific craft breweries and awesome restaurants. At the other, go luxe at the Camden Harbour Inn, a boutique property of Relais & Chateaux pedigree with an enviable location near the harbor action.
Courtesy The BetsyFlorida beach bliss: Miami Beach to New Smyrna
With scenes that are both cocktail- and kid-friendly, Florida has beautiful beaches to suit every personality. Experience some of the Sunshine State’s superlative spots with a road trip that covers most of 339-mile highway A1A, starting in the flash of South Beach and ending in the unexpected surf town of New Smyrna Beach. After your fill of Art Deco, beautiful people, and parties in Miami Beach, inch up to the wide, sparkling beaches of Fort Lauderdale. Gawk at the mansions of tony Palm Beach and later cross over to the nature-steeped environs of Vero Beach, Melbourne Beach, and Merritt Island, where manatees, sea turtles, and seabirds rule.
Where to stop: Participate in naturalist-led turtle walks during nesting and hatching seasons (June-September annually) at Archie Carr National Wildlife Refuge. Located between Melbourne Beach and Wabasso Beach, the Refuge is the world’s most significant area for loggerhead sea turtle nesting and North America’s most significant area for green turtle nesting. In New Smyrna Beach, hang ten or simply immerse yourself in the surf culture of this small stretch of Florida, which often receives accolades as one of the top surf towns in the U.S.
Where to eat: Experience the Miami trend of restaurant-club hybrids that promise fine dining early evening but all-out throwdowns until the wee hours. Check out downtown’s Sexy Fish, an ocean-themed, seafood-centric, Asian restaurant that dazzles by design, with over-the-top, aquatic-imbued glass mosaics and sculptures plus works by the likes of Damien Hirst and Frank Gehry. On the beach, dress to impress at MILA, a vibe-heavy rooftop Mediterrasian restaurant that attracts Miami’s style set.
Where to stay: To truly take in the pulse of South Beach, consider staying at The Betsy - South Beach, 1 Hotel South Beach, or The Setai Miami Beach—all 2021 Readers’ Choice Award winners. Upon reaching the quieter shores of A1A, settle into a room at the Kimpton Vero Beach Hotel & Spa, located on Central Florida's Treasure Coast.
Clay Banks/UnsplashBrooklyn goes bucolic: A trip up the Hudson Valley
Many New Yorkers will tell you that the Hudson Valley makes for a great trip no matter how much time you have to spend—a day trip, short and sweet overnight, or a weekend getaway road trip from the city, you name it. Zip upstate on I-87 and meander through Beacon, Kingston, and Hudson, each with its own country-cool “over the city thing” vibe (think: Brooklyn in the woods). These destinations can be a road trip on tracks, too. Just hop aboard the Metro North.
Where to stop: A favorite Hudson Valley attraction is Storm King, a 500-acre sprawling lawn where you’ll find sculptures galore and more in an outdoor museum. If you don’t bring your own, rent a bike for the downhill adventure at Windham Mountain Bike Park, the longest jump trail on the East Coast, located about 30 miles west of Hudson.
Where to eat: Backbar may look like an antique garden shop, but it’s actually a bar. The creation of Zak Pelaccio (formerly of Manhattan’s Fatty Crab) is worth driving two hours to Hudson just for the dumplings and tequila-spiked-slushies. In Beacon, sample chef Brian Arnoff’s multi-course menu at his wildly popular Kitchen Sink Supper Club. The menu changes every four weeks based on what’s in season and available and is offered exclusively on Fridays and Saturday evenings.
Where to stay: Make a home base in Kingston at Hotel Kinsley, which is housed in a former State of New York bank building and offers high design in a low-key environment. Alternatively, book Hutton Brickyards, located on a 73-acre riverfront campus that was once home to a brick factory.
Nataliia Kvitovska/UnsplashNorthern exposure: The Cabot Trail, Nova Scotia
Okay, this one's going to mean crossing a border, but the minor inconvenience is well worth it. Head north—way north—to the tip of Atlantic Canada for the 185-mile Cabot Trail, a highly rewarding loop through the wilds of northeastern Nova Scotia, hugging the craggy coastline of Cape Breton Island and traversing the canyons and valleys of Cape Breton Highlands National Park. The well-marked trail is dotted with small towns, fishermen villages, lighthouses, and pubs as colorful as the locals.
Where to stop: Stop in Chéticamp for a riveting zodiac whale watching experience and the chance to see some 10 species in their natural environs (Charismatic pilot whales are most often sighted). Captain Zodiac leads tours during the migratory season (June to September) to marvel at these highly intelligent creatures.
Where to eat: Grab a seat on the oceanfront terrace, and feast on fresh lobster rolls or grilled haddock and scallops at no-frills, Nova Scotian mom-and-pop Seagull Restaurant in Ingonish.
Where to stay: Unpack at the 72-room, waterfront The Lodge at Cabot Links. Golf enthusiasts will appreciate its world-renowned courses, but non-golfers can simply enjoy the views and comforts of the most modern accommodation in all of Cape Breton and a home base from which to explore the far reaches of the Cabot Trail.
GettyHistoric southeast: St. Augustine, Florida to Charleston, South Carolina
Journey through coastal American history—and the southern spaces that fully embrace their historic allure—starting at the nation’s oldest city (c. 1565), Spanish-influenced St. Augustine. Then, head to the South’s two most iconic cities, Savannah and Charleston, linked by US-17, where horse farms and churches mix with war relics and towering oak trees. After taking in all the southern charms of Charleston, continue to the tranquil beaches of Sullivan Island.
Where to stop: In St. Augustine, visit the famed yet kitsch “Fountain of Youth” (yes, that Fountain of Youth.) Between Savannah and Charleston on US-17, stop at lesser-known historic site Sheldon Church Ruins, the remains of a circa-1753 church set ablaze first by the British during the Revolutionary War and then by the Union Army during the Civil War.
Where to eat: Savor the cuisine of Charleston's it chef, James Beard winner Mike Lata, at his two institutions, The Ordinary and FIG (which stands for Food is Good). Experience the apex of low country fare at Circa 1886, where Executive Chef Marc Collins uses regional ingredients and reinterprets recipes and dishes of decades past to create thoughtful dishes that keep culinary history in style (Don’t miss the “Southern Grilled Cheese” a pillow of grilled brioche stuffed with pimento cheese mousse, Surryano ham, and paddlefish caviar).
Where to stay: Stay in the center of Charleston’s historic district at The Charleston Place. Formerly part of the Belmond collection, this iconic hotel has gone independent under the direction of new ownership, which is infusing some $200 million into the storied property.
