This article is part of our America 250 coverage. See more stories on epic adventures, music and culture festivals, unexpected experiences, and signature foods to eat in each of the 50 states (plus D.C. and Puerto Rico).
Few travel experiences are as quintessentially American as the road trip: a fueled (or charged) up car, a loose itinerary, and the promise that something exciting waits just past the next curve. For generations, loading up the car has been a rite of passage—equal parts discovery and reinvention. As the country approaches its 250th anniversary, we’re celebrating that restless spirit with unforgettable drives in each state. In this list, we’re focusing on drives in the Northeast, but we also have picks for the best road trips in the West, the Midwest, and the South.
These nine northeastern road trips wind from the rocky coast of Maine to the Appalachian Mountains, plus plenty of small-town charm to see in between. Together, they start to form a portrait of the United States best understood not from 30,000 feet—but mile by mile.
Connecticut for spring blooms in small-town New England
- Start: Norwich
- End: Woodstock
- Distance: 39 miles
If you’re a fan of quaint towns and farmsteads, this road trip may be for you. (Fun fact: Woodstock has more dairy farms than anywhere else in the state.) The route, on I-395 North, could be driven in under an hour, but you’ll want to slow down and take your time—yep, it’s that scenic. Do some bird-watching at Aicher Preserve or Border Woods Preserve, both of which come alive with greenery and flowers in spring. The manicured gardens will be in full bloom at Roseland Cottage in Woodstock, a pretty 1846 Gothic revival–style former summer home that’s a history museum. Bed down for the night at the Inn at Woodstock Hill, where you can enjoy Connecticut’s serenity near the small town of Putnam. —Chloe Arrojado
Maine for coastal scenery and lobster in every form
A Maine road trip is all about the sea, whether it’s lobster rolls from Barnacle Billy’s in Perk Cove or coastal trails in Acadia National Park.
Photos by Michelle Heimerman
- Start: Ogunquit
- End: Acadia National Park
- Distance: 232 miles
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 lobster 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 150-year-old classic White Barn Inn & Spa, 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 tantalizes in the lobster roll at Five Islands) and Rockland (with a lively arts scene on Main Street). Windsor Chairmakers sells exceptionally well-crafted furniture made from fine woods in Lincolnville.
Finally, 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 crustaceans you’ve enjoyed on the way here. —Ray Rogers
Massachusetts for family museums and literary landmarks
- Start: Springfield
- End: Deerfield
- Distance: Approximately 35 miles
Searching for a family road trip that weaves together creativity and literature? Steer to the I-91 corridor that slices through central Massachusetts to find museums, natural wonders, and sports stars all within a 50-mile radius. Threaded by the Connecticut River, the region that locals call the Pioneer Valley is lined with verdant fields and graced by wooded hills.
Family-friendly stops include the Dr. Seuss National Memorial Sculpture Garden and the Naismith Basketball Hall of Fame in Springfield (the latter showcases a pair of Shaquille O’Neal’s size 23½ sneakers); the Beneski Museum of Natural History in Northampton, which has an Ice Age mastodon and mammoth skeletons on display, and the Eric Carle Museum of Picture Book Art, with art by the author/illustrator of The Very Hungry Caterpillar; and the Magic Wings Butterfly Conservancy & Gardens in Deerfield. While sitting surrounded by flowers, trees, and water features, visitors can watch as citrus swallowtails, zebra longwings, orange tips, and dozens more species flutter about and perch on shoulders. Up to 3,000 graceful creatures live in the 80-degree warmth of the enclosed tropical garden. Also on view are birds, reptiles, and fish, which make this place an indoor nature adventure. After sleuthing on scavenger hunts, look for bountiful books and butterfly gifts in the shop. —Barbara Wysocki
New Hampshire for Kanc views and White Mountain trails
The Kancamagus Highway, or “Kanc,” is a prime fall foliage route.
Photo by Wangkun Jia/Shutterstock
- Start: Conway
- End: Lincoln
- Distance: 35 miles
Curving through New Hampshire’s White Mountain National Forest, the Kancamagus Highway has earned its place on several “best of” road trip lists, thanks to its picturesque ponds, hiking trails, scenic overlooks, and hairpin turns. Colloquially known as the “Kanc,” the byway draws millions of visitors every year. With the highway’s plentiful hiking trails taking up daylight, spend the night in one of the six White Mountain National Forest campgrounds located on the byway. —Chloe Arrojado
New Jersey for boardwalks and beach towns bookended by nature reserves
- Start: Sandy Hook
- End: Cape May
- Distance: Approximately 125 miles
Any Garden Stater will tell you: There is nothing like the Jersey Shore anywhere. It went through a period of questionable reputation during the run of that MTV show, but it’s retained its quirky charm to this day even as towns grow, expand, and develop.
Start a shore-sampler road trip in Gateway National Recreation Area in Sandy Hook, the northern tip of a necklace of barrier-island beaches that stretch all the way down the state. Walk or bike along trails and visit the lighthouse, then drive about a half hour south on Ocean Avenue to Asbury Park for a stroll on the historic boardwalk with its 1929 copper-clad Carousel Building (and, come nightfall, a concert at the nearby Stone Pony, made famous by Bruce Springsteen).
Then go full Jersey Shore in Point Pleasant. Here, the beach is wide and filled with families, and Jenkinson’s Boardwalk has all the iconic NJ ingredients: rides, games, mini golf, a fun house, plus shore-specific snacks, including saltwater taffy, funnel cake, and fudge in a dozen flavors.
For the final leg, you have a choice. You can detour onto 18-mile Long Beach Island for quieter, silkier sands, (mostly) residential towns, and handsome mansions, or you can drive to the southern tip of the state to the fraternal-twin towns of Wildwood and Cape May. (Pro tip: Skip Atlantic City, which is all casinos, bright lights, and big hotels.)
Wildwood (another barrier island) is the livelier sibling, with wide free beaches, a lively and well-known boardwalk, and plenty of nightlife. Cape May is a little more grownup and relaxed: colorful Victorian houses (the Emlen Physick Estate is a preserved one from 1879), a pedestrianized town with shops and restaurants, a lighthouse, and the Cape May National Wildlife Refuge where you can stretch your legs on a hiking or biking trail as you listen to the sounds of the Atlantic. —Billie Cohen
New York for art pilgrimages and mountain retreats
Storm King is a 500-acre outdoor museum of large-scale installations; end the night with dinner at Chleo, one of the stylish restaurants that makes the town of Kingston feel like Brooklyn North.
Photo by Mengwei Lin/Unsplash (L); Michelle Heimerman (R)
- Start: New York City
- End: Woodstock
- Distance: 142 miles
There’s a world of art and culinary treasures just outside New York City that’s worth exploring as well, not to mention scenic mountain ranges and preserves. Cross the GW Bridge out of Manhattan 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 Storm King, travel another 22 miles 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.
Take time the next morning to view the impressive art collection at Dia Beacon (the Dan Flavin installations are worth the trip alone) before continuing on to Mohonk Mountain House, where you spend a few days soaking up the Old-World rustic feel and immersing yourself in nature. Canoe in the pond, hike the magnificent property, or rock climb the Shawangunk Mountains in nearby Mohonk Preserve. Drive through adorable towns like Rosendale (where the Six Bells Countryside Inn opened last year) and High Falls on your way to Kingston, which has become a bit like Brooklyn North. Get dinner at Chleo, a wine bar with a vegetable-forward menu and wood-fire cooking.
End your trip 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 impressive dining options like Southeast Asian–inspired Good Night, tastefully curated boutiques like the upstate outpost of Brooklyn’s Casa Ziki for some colorful and modern design gifts, and a killer bookshop, the Golden Notebook. For a quirky stay, consider the Herwood Inn, with four suites paying homage to female music icons. —Ray Rogers and Michelle Heimerman
Pennsylvania for modernist marvels and mountain rapids
- Start: Pittsburgh
- End: Ohiopyle
- Distance: Approximately 71 miles
If you’re visiting Pittsburgh, rent a car and head southeast to the small mountain community of Mill Run to see Fallingwater. Does the word “masterpiece” get overused? Perhaps. But a visit to the UNESCO World Heritage site makes a compelling case that this former residence—dramatically cantilevered over an active waterfall—is architect Frank Lloyd Wright’s crowning achievement.
Even with ongoing preservation work, the excursion is well worth planning ahead (entry is timed and ticketed, so book in advance). Docents offer encyclopedic insights, and you’ll have time to study the original furnishings, artwork, and design elements that remain meticulously preserved—including a fireplace outfitted with a crane-arm kettle, perfect for imagined evenings in the sunken living room. Continue the theme of vertiginous water with the five-minute drive south to Ohiopyle State Park. Spanning 20,500 acres of Appalachian wilderness, the park contains 79 miles of trails and more than 30 cascading streams. Hike to Cucumber Falls or Meadow Run for primo waterfall action and, in the summer months, cool off by taking a dip (conditions permitting).
If you’re short on time, you can view Ohiopyle Falls from an observation area just off Main Street, where kayakers often jettison themselves off the 20-foot drop into the Youghiogheny River. For a more adrenaline-fueled finale, join a guided white-water rafting trip through the Class III and IV rapids of the Lower Yough. —Jennifer Hope Choi
Rhode Island for lighthouses, lobster rolls, and haunted lore
Newport is famous for its Gilded Age mansions, many of which are open for tours.
Photo by Kumar Mehul/Unsplash
- Start: Narragansett Bay
- End: Newport
- Distance: 45 miles
Rhode Island’s license plate reads “Ocean State,” and a drive along even a slice of its 400-mile shoreline makes the nickname obvious (impressive for a state only 48 miles long and 37 miles wide). This coastal route passes lighthouses, scattered islands, and stretches where you’re practically driving on the sand.
Start at Point Judith Lighthouse, a brick beacon used during World War II, before heading north on Ocean Road as it hugs the shoreline. Stop at Black Point Trailhead to photograph the ruins of a century-old carriage house or hike the easy 1.8-mile trail to sweeping views of Narragansett Bay. In Narragansett proper, grab a chilled lobster roll and the city’s namesake beer at the Coast Guard House, or take your meal to Town Beach, framed by the hulking Towers—remnants of an 1886 seaside casino.
Continue north on Route 1A and cross the Jamestown Verrazano Bridge to Jamestown, an island known for its shingle-style cottages and historic lighthouses, including Beavertail, which also houses a shipwreck museum. At Fort Wetherill State Park, trails wind past abandoned WWII structures and down to a quiet beach. (A scene from Wes Anderson’s Moonrise Kingdom was filmed here.)
Get a milkshake or ice cream sundae at Sugar Shack at the Ferry Wharf, then drive over the Newport Bridge and detour along Ocean Avenue for views of coves and rocky outcroppings. From there, turn onto Bellevue Avenue to see Newport’s most famous Gilded Age mansions, including the Vanderbilt family’s opulent estate. Check in at the Vanderbilt, an Auberge Collection property in downtown Newport with pinstripe-wallpapered rooms and classes in cocktail making or yachting-bag customization. Finish at White Horse Tavern—the oldest, continuously operating restaurant in the USA, and, according to lore, haunted—for a bowl of clam chowder or the beef Wellington. —Danielle Hallock
Vermont for snowshoeing, sleigh rides, and fireside inns
- Start: Wilmington
- End: Stowe
- Distance: Approximately 170 miles
Vermont infallibly feels cozy, whatever the time of year. Winter undoubtedly takes the cider doughnut, though: nostalgic towns decked out for the holidays, après-ski haunts with fireplace seating, enchanting historic inns, and snow-filled scenery. There’s a reason Vermont villages are considered “Hallmark movie towns.”
This four-day itinerary starts in the town of Wilmington, one of southern Vermont’s tiny treasures, with breakfast at Dot’s of Vermont, a lively old-school diner popular with locals and visitors alike. After wandering around the appealing downtown, head to Mount Snow Ski Resort, where you can buy a half-day afternoon ticket at the window. (There is also a tubing park, if that’s more your speed.)
The next day, take the back roads on the way to Woodstock: The drive along forest-fringed Routes 100 and 106 North, with sprawling farms and covered bridges, is an activity unto itself. In a little under two hours, you’ll pull into a real-life postcard. Hop on a horse-drawn sleigh ride through snow-covered fields at Billings Farm & Museum; reserve a riverside sugar shed at Long Trail Brewing Co. for the ultimate Vermont winter brewery experience; and settle in for the night at the Woodstock Inn & Resort, an 1800s-era New England hotel. Head out of Woodstock bright and early, but not without getting a cruller in flavors like maple or apple cider crumb at Farmer and the Bell.
The first portion of the drive today takes approximately 40 minutes and lands you at one of Vermont’s top ski resorts: Killington, aka “the Beast of the East.” After skiing, set aside two hours to get back on Route 100 and drive past the roadside waterfall Moss Glen Falls (which might be partially frozen in winter) to Stowe. Here, you can settle into your room at the Brass Lantern Inn, a family-run bed-and-breakfast in an early 19th-century farmhouse.
After a restful night’s sleep, it’s time for more adventures in Stowe: skiing and snowboarding at Stowe Mountain or a one-of-a-kind snowshoeing experience at Smugglers’ Notch, known for its narrow mountain pass with giant boulders, waterfalls, caves, and hiking trails. —Lauren Breedlove
Related: 4 Days in Vermont: Sleigh Rides, Waterfall Snowshoeing, Après Ski Hangs, and Maple Doughnuts
