Best of New England Road Trip
Home to America’s oldest cities, New England is where the past meets the present meets spectacular scenery. From rugged coastlines to soaring mountains, quirky coastal towns to sprawling cities, historic dwellings to modern museums, New England is a world within itself. In one short trip, you’ll criss-cross this vibrant region where you’ll dine on fresh seafood, walk along pristine shorelines, breathe in fresh mountain air, mingle with artists and intellectuals, and explore the rich cultural history on this bucket-list New England road trip.
History Was Made in Massachusetts
Your adventure kicks off in Boston, one of the oldest cities in the US and the largest in New England. Here, you’ll find a modern metropolis that’s steeped in history. Walk down the cobblestone streets of Boston’s Historic Districts and you’ll find yourself connected to the history of America’s freedom. It’s guts and glory, intellect and independence, history and modernity. Oh, and it’s Red Sox baseball.
Head down the Freedom Trail, a walking route in the heart of downtown, where you’ll visit some of Boston’s most historic sites and learn their roles in the American Revolution.
Next, wander through the picturesque Beacon Hill among rows of historic Victorian brick and Federal-style buildings. Then it’s off to “America’s Most Beloved Ballpark,” Fenway Park, for a fascinating tour of the home of the Red Sox.
From Boston, hit the road and head north to Salem, a city famous for its spooky history. It’s here that in 1692 several locals were tried and executed for practicing witchcraft in an event known as the Salem witch trials.
Salty Air + Historic Flair in New Hampshire
Continue your journey up the coast to the charming port town of Portsmouth, New Hampshire. Here, you’ll wander through the Strawbery Banke Museum where you’ll explore over 30 historic buildings that display New England’s architecture and learn traditional crafts from period-costumed artisans all while breathing in salty sea air.
Maritime + Mountains in Maine
Then it’s on the road to Kennebunkport, a quaint coastal resort town in Maine. Formerly a ship-building capital, Kennebunkport is home to a thriving maritime culture and spectacular beaches, including Goose Rock Beach, which offers miles of pristine white sand.
After soaking up the sun, head to Dock Square to peruse the windows of picturesque shops and upscale galleries tucked inside historic Federal-style buildings.
From Kennebunkport, journey to Bar Harbor, where rich history meets stunning mountain scenery. Home to multiple historic mansions, Bar Harbor was once a popular resort destination for New England’s elite. Today, this coastal town is best known as the gateway to Acadia National Park.
Rocky coastlines, ferocious waves, and towering mountains are just the tip of what this park has to offer. Drive to the summit of Cadillac Mountain, the tallest peak in the park, for breathtaking views of the surrounding landscape and Frenchman Bay. Then refuel with fresh local fare from the lobsterman owned and operated Travelin Lobster restaurant.
Woods and Local Goods in Vermont
Cruise west through the White Mountains, also known as the “Rooftop of New England,” where you’ll wind through pristine wilderness and pockets of picturesque towns; cross historic covered bridges and hear the sounds of clear mountain streams until you reach the tiny town of Greensboro.
Here, you’ll make a quick stop at Willey’s General Store to pick up local provisions like fresh-from-the-farm maple syrup, Hills Farmstead Brewery craft beer, and Jasper Hill Farm cheese.
Then, it’s off to Stowe, a quaint 200-year-old village, dramatically backdropped by Mount Mansfield, where you’ll find some of the state’s premier skiing and outdoor destinations.
Culture Calls in The Berkshires
Your New England adventure continues west in the Berkshires. This rural region in the Massachusetts mountains is dotted with charming towns. A popular vacation spot, the Berkshires is where artistic, academic, and outdoor cultures collide.
Head to the Berkshires town of Williamstown, known for its art institutions, where you’ll ponder world-class collections at the Clark Art Institute and the Williams College Museum of Art.
Then, it’s off to the town of Lenox whose roster of past and present residents reads like a record of society’s upper echelon. It’s also where you can dine, stay, and enjoy a spa day at some of the world’s most stunning hotels, including Blantyre, a luxury country mansion, and Wheatleigh, a sprawling 1893 Italianate mansion.
Take a tour of the Mount, the spectacular mansion of renowned author, Edith Wharton. Or head to Tanglewood music venue where you can catch an awe-inspiring open-air performance from the Boston Symphony Orchestra in the summer.
Explore the Riches in Rhode Island
From the mountains to the coast, you’ll cruise east until you reach the city of Newport in Rhode Island. Nestled on Aquidneck Island off Narragansett Bay, this vibrant city was once the summer home of America’s wealthiest families who, in the 1800s and early 1900s, built grandiose mansions, many of which are now museums.
To get a taste of this Gilded Age, it’s off to tour Newport’s most historic mansions, including The Breakers, a Renaissance-style home built in 1895 for the Vanderbilt family.
Shorelines + Quaint Shops in Cape Cod
Cruise control east until you reach Cape Cod, a hook-shaped peninsula on the Atlantic Ocean. Here, you’ll find yourself surrounded by seabirds and sand dunes, quaint cottages and historic lighthouses.
Stroll through the pristine sandy beaches of the Cape Cod National Seashore. Then head to Provincetown where you’ll find row after row of shops and eateries on the creative and quirky Commercial Street.
Back to Boston
It’s an hour and a half drive back to Boston. But before your adventure ends, there’s still time for one more bite of New England. Head to James Hook & Co. on the downtown waterfront for a cup of creamy clam chowder or fresh-caught lobster.
11 nights' accommodation, driving instructions, sightseeing maps + ideas.
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