Two-Week New England Road Trip Itinerary

A great loop through American history, high peaks, and picture-perfect countryside, this two-week New England road 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 in miles, this gives you the lay of the land and the very best of New England.

looking up at the front gate of the Massachussets State House
The Massachusetts State House. Photo © Jen Rose Smith.

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.

On your second day, hop a ride on a swan boat in the Boston Public Garden. Then explore 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 fabulous 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 sabotage.

bright pink and orange sky behind Portland Head Lighthouse
Sunrise at Portland Head Light in Maine. Photo © Cynthia Farr-Weinfeld/Maine Office of Tourism.

Days 3-5: Coastal Maine and Acadia

270 miles, 5.25 hours

Stop by Caffe Vittoria in the North End for an old-world cappuccino before picking up some wheels and heading to Portland, an easy, two-hour drive up the interstate. Before you reach the city, make a short detour to a trio of lighthouses in Cape Elizabeth. Portland Head Light is easily the most picturesque, but the pair of lighthouses known as Two Lights are a stone’s throw from classic lobster rolls at The Lobster Shack.

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 mail boat that connects the bay’s islands to the mainland—then kick off the evening by visiting some of the city’s award-winning microbreweries.

On your second day on the coast, make an essential breakfast stop at Portland’s Holy Donut, then hit the road for a day of 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, 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.

Mount Washington view from the shore of Lakes of the Clouds
Mount Washington summit from Lakes of the Clouds. Photo © Jen Rose Smith.

Days 6-7: White Mountains

215 miles, 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. Stretch your legs after the long drive on the easy walk to Diana’s Baths, a series of small 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 in town.

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. For all of the mountain scenery and fewer crowds, opt for a trek up Franconia Ridge instead, choosing from a series of 4,000-foot peaks with views of the valley below.

barn in Woodstock, Vermont
Woodstock is a rural escape. Photo © Albert Pego/iStock.

Days 8-9: Southern Vermont

165 miles, 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. Spend an evening exploring Brattleboro’s art galleries, or catch a circus performance at the town’s New England Center for Circus Arts.

trees surrounding the Mount Greylock summit
Summit marker at Mount Greylock. Photo © Jen Rose Smith.

Day 10: The Berkshires

80 miles, 2 hours

Watch the mountains taper 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 cutting-edge 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.

people standing on the foot path of the Cliff Walk
The narrow Cliff Walk path threads between Newport’s most elegant homes and the rocky edge of the Atlantic Ocean. Photo © Jen Rose Smith.

Day 11: Newport

165 miles, 2.75 hours

Keep pointing for the coast and you’ll wind up in this pretty port city, where the waterside Cliff Walk cuts past some of the grandest Gilded Age estates in New England. With just one day in town, pick a single mansion to explore before hitting the beach for clam rolls, sand, and sun. When the sun begins to slip, hop on scenic Ocean Drive to take in the coast with a stop at Castle Hill Inn for sundowners on The Lawn.

lightouse on the coast of Cape Cod
Brant Point Lighthouse in Cape Cod. Photo © Alwoodphoto/

Days 12-13: Cape Cod

120 miles, 2.5 hours

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 a beeline 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. 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.

women walking on a boardwalk in Sandwich
The boardwalk to Town Neck Beach in Sandwich. Photo © Cape Cod Chamber of Commerce/Bill DeSousa.

Day 14: Boston

115 miles, 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.

Jen Rose Smith

About the Author

Jen Rose Smith came to Vermont for the mountains and lake, then stayed for everything else. She spends her time exploring the state on bicycles and backcountry skis with her husband, Daniel, searching out the sweetest picnic spots, swimming holes, and snack bars.

Jen is a freelance writer whose work on travel, food, and drink has appeared in Best of Burlington, Local Banquet of Vermont, Vermont Magazine, Traveler’s Tales: Best Women’s Travel Writing, Culinate, and Overnight Buses. Since settling in Vermont, she’s continued to travel extensively, hunting iguanas in Mexico, cooking in Italy, and riding her bicycle across Newfoundland’s wilderness. Her adventures in Vermont while researching and writing this book have been just as compelling, and there’s no other place she’d rather live.

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