Two-Week New England Road Trip Itinerary
An epic loop through American history, high peaks, and picture-perfect countryside, this two-week trip is a “grand tour” in every sense. The full itinerary means quite a bit of time on the road, so those looking for a more leisurely vacation should snip out bits of this route in exchange for extra beach days, hikes, and free time to explore along the way. But if you’ve got an itchy pedal foot and the urge to put some miles on the odometer, this gives you the very best of New England.
Days 1-2: Boston
Get a crash course in Revolutionary history on the Freedom Trail, which stretches from the shiny dome of the Massachusetts State House to the Bunker Hill Monument. Don’t tackle the whole thing at once—the trail isn’t complete without a lunch break in the Italian American North End neighborhood. Try Italian ice, cannoli, or a classic submarine sandwich before crossing the Charles River toward the USS Constitution. Take a sunset stroll at Arnold Arboretum on the Emerald Necklace and find your way from there to Jamaica Mi Hungry for coconut shrimp and jerk pork shoulder.
On your second day, take a field trip from the city to Walden Pond for a serene swim. From there, backtrack to the city, grab a nourishing sandwich from Flour Bakery + Café, and spend the afternoon exploring Back Bay’s art and architecture; duck into the sanctuary of Trinity Church, soak up the scholarly atmosphere in the Boston Public Library reading room, then stand in the center of the world at the stained glass Mapparium. Spend the afternoon in one of Boston’s world-class museums, taking in ancient artifacts and contemporary art at the Museum of Fine Arts, or head to the Boston Tea Party Ships and Museum to reenact the city’s favorite piece of colonial-era civil disobedience. At dusk, saunter over to the South End for a glass of wine and succulent hand-made pasta at MIDA.
Days 3-5: Coastal Maine and Acadia
275 mi/443 km, 6 hours
Stop by Caffe Vittoria in the North End for an old-world cappuccino before procuring some wheels and heading to Portland, an easy, two-hour drive up the interstate. Before you reach the city, make a detour to the Wells Reserve at Laudholm for a biodiverse stroll through maples and cedars, sandy beaches, and briny estuaries. The reserve is conveniently located just down the road from Kennebunkport favorite Port Lobster.
Get a taste of Portland’s maritime life on a boat tour of Casco Bay—hop a historic schooner or take a ride on the mailboat run that connects the bay’s islands to the mainland—then kick off the evening by visiting some of the city’s award-winning microbreweries like Bissell Brothers and Foundation.
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On your second day on the coast, enjoy a decadent breakfast at Portland’s Holy Donut, then hit the road for lighthouse-hopping and harbor-strolling. Drive up to Bath and work your way through the Maine Maritime Museum, or go a bit farther to Rockland and take in three generations of Wyeths at the Farnsworth Art Museum before visiting nearby Owls Head Light. Pick up a picnic lunch to eat near Rockport’s idyllic harbor, then visit the nautical boutiques in downtown Camden. Make the final push to Acadia National Park on Mount Desert Island, recover with noshes and lager at Mainely Meat BBQ, and turn in early if you’re planning to catch sunrise on Cadillac Mountain, a pilgrimage place where you can see the first sunlight hit the coast.
After your morning’s start, mountaintop sunrise or not, enjoy the rest of the day car-free in the national park; rent a bike, hop the free Island Explorer shuttle, and cruise the extensive network of carriage trails that link great stone bridges, viewpoints, and rolling mountains. For the real experience of a Maine lobster dinner, cross the island to Thurston’s Lobster Pound to get one with all the fixings at the edge of a scenic harbor.
Days 6-7: White Mountains
215 mi/346 km, 4.75 hours
The route to the White Mountains crosses the dark, deep forests of inland Maine, ticking off a series of towns that recall the state’s immigrant heritage: Pass Naples, Sweden, and Denmark on your way to the outdoor mecca of North Conway. Nab some thin-crust pizza from Flatbread Company and then stretch your legs after the long drive on the easy walk to Diana’s Baths, a series of waterfalls perfect for an early evening dip (if there’s enough water). Fortify yourself for a day in the mountains with dinner and a locally brewed beer at Moat Mountain Brewery & Smokehouse.
Day two is all about mountain peaks and rugged scenery: Chug to the top of Mount Washington on the 150-year-old cog railway, or hike the mountain yourself—on a clear day at the summit you’ll have views stretching from Maine to New York’s Adirondack Mountains, and you can watch a steady stream of Appalachian Trail through-hikers pose for photos at the top. And once you’re back in the valley, you can motor over to Littleton for some savory riverside noodles and curry at Taste The Thai & Sushi House. For all of the bucolic scenery and fewer crowds, take a journey into Evans Notch instead, choosing from a series of gusty peaks with panoramic views of nearby valleys and mountain ranges.
Days 8-9: Southern Vermont
165 mi/266 km, 3 hours
Take the Kancamagus Highway for a swooping, scenic drive through the mountains on your way to Woodstock, where you’ll find a classic village green, art galleries, and farm-to-table restaurants in a lush river valley. Hop a wagon ride, learn to churn your own butter, and get friendly with some Jersey cows at the Billings Farm & Museum, then spend the afternoon visiting classic covered bridges.
The drive from Woodstock to Brattleboro is another stunner, especially if you take the scenic route: Visit the President Calvin Coolidge State Historic Site to see his family homestead on your way to Route 100, then wind through pretty villages like Grafton. After culminating the day’s journey with kebabs and springy salads at Tulip Bar and Restaurant, spend an evening exploring Brattleboro’s art galleries, or catch a circus performance at the town’s New England Center for Circus Arts.
Day 10: The Berkshires
80 mi/129 km, 2 hours
Watch the mountains fade into gentle hills as you make your way south, and choose a couple of the region’s best destinations for a classic Berkshires day: Spend the morning with adventurous modern art in North Adams at the MASS MoCA or follow in Thoreau’s footsteps to the top of Mount Greylock. After lunch, continue south to Lenox to visit the elegant home of Edith Wharton, then spend a quiet evening in the Brava wine bar, mingling with musicians from nearby Tanglewood.
Day 11: Newport and Providence
190 mi/306 km, 3.5 hours
Keep pointing toward the coast and you’ll wind up in the pretty port city of Newport, where the waterside Cliff Walk cuts past some of the grandest Gilded Age estates in New England. Pick a single mansion to explore before hitting the beach for clam cakes, sand, and sun. As the sun sets, zip up to Providence for a twilight meander on the RiverWalk and follow it with a parade of fresh-caught fish crudo at Oberlin.
Days 12-13: Cape Cod
120 mi/193 km, 2.25 hours
Snag some fresh baklava at Aleppo Sweets and drive all the way to “the end of the world”—that’s colorful, creative Provincetown to you—to spend your last days exploring Cape Cod. Make for the Cape Cod National Seashore when you arrive, where you’ll find the finest beaches in New England, crumbling cliffs, and historic lighthouses, and spend a day wandering the sand.
The next day, get a taste of Provincetown’s artistic heritage by strolling the downtown galleries, then join a tour of the rustic artists’ shacks scattered through the rolling dunes. Power up for the evening with surf and turf cooking at the Canteen, see if you can keep up with the locals at a raucous tea dance, then spend a night on the town in true P-town style with tickets to a drag show.
Day 14: Boston
115 mi/185 km, 2.25 hours
Start your last day of New England adventures with some pastries from the Portuguese Bakery, then hit the Cape Cod Rail Trail for a morning of exploring on two wheels. If you have time, break up the return drive to Boston with stops in one or more of the villages that line the Inner Cape: Visit Chatham’s pretty lighthouse, play a round of pirate-themed minigolf in Yarmouth, or see a classic saltbox home in old-fashioned Sandwich. And consider a “last supper” of golden fried clams at Seafood Sam’s before crossing the bridge to the mainland.
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