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Massachusetts’ 6 best road trips / Lonely Planet / WEEKLY TRAVEL & LIFESTYLE MAGAZINE / 2020 / NOVEMBER / 07 / 14

A Massachusetts road trip shows off four centuries of dramatic history © Holly Hildreth / Getty Images
City streets and cow-dotted pastures, windswept beaches and forest-covered mountains: Massachusetts offers an incredible diversity of landscapes. The state is small, but its scenery will satisfy your craving for eye candy (surely the foremost requirement for a rewarding road trip).
When you’re ready for a pit stop, the Commonwealth has you covered, with a tantalizing spread of local specialties, such as fruit and vegetables straight from the farm and succulent seafood right out of the ocean. So fuel up, because you have a lot to do.
Massachusetts trips show off four centuries of dramatic history, rich displays of artistry and creativity and thrilling opportunities for outdoor adventure. Here are the six best Massachusetts road trips. 
Editor’s note: Please check the latest travel restrictions before planning any trip and always follow government advice.
Scenic Autumn Road in the Quabbin Reservoir Park area of Massachusetts

A Massachusetts road trip offers a glimpse of history and outdoor activities © Denis Tangney Jr / Getty Images
Coastal New England 
Travel stats: 6-8 days; 240 miles 
This drive follows the southern New England coast. A week of whale-watching, maritime museums and sailboats will leave you feeling pleasantly waterlogged.
From a pirate’s perspective, there was no better base in Colonial America than Newport, given the easy access to trade routes and friendly local merchants. Until 1723, that is, when the new governor ceremoniously hanged 26 sea bandits at Gravelly Point. This classic trip highlights the region’s intrinsic connection to the sea, from upstart pirates to upper-crust merchants,
from Gloucester fisherfolk to New Bedford whalers, from clipper ships to submarines.
Pilgrim Trail 
Travel stats: 4-5 days; 147 miles
Your car is a time machine, transporting you back 400 years. The region’s living museums allow you to experience firsthand what life was like for the colonists as they settled in the New World.
Explore the sites and structures – churches and trading posts, homesteads and grist mills – that are still standing from those early days.
A red and white small lighthouse sits next to a cape cod house in front of a road.

Don’t let the cool temperatures keep you from a Cape Cod road trip © Kickstand / Getty Images
Cape Cod & the Islands 
Travel stats: 5-7 days; 128 miles 
A drive down the cape offers a beach for every mood. Besides sun, surf and sand, there are lighthouses to climb, oysters to eat, art and antiques to buy, and trails to hike.
As the sun sets and the sky darkens, you slide your car into place alongside dozens of others facing the massive screen. Roll down the window, feel the salty breeze and recline your seat.
After an exhilarating day at the beach, it’s time to sit back and enjoy a double feature at the drive-in. Sounds like something out of a 1950s fantasy? It’s summer on Cape Cod.
Epic drives Spotify playlist 
Around Cape Ann 
Travel stats: 2-3 days; 54 miles
Somebody – a New Englander, no doubt – once said that “the humble clam…reaches its quintessence when coated and fried.” The big-bellied bivalve – lightly battered and deeply fried – supposedly originated in Essex, Massachusetts, so Cape Ann is an ideal place to sample the New England specialty.
This North Shore route takes you from clam shack to clam shack, with breaks in between eating for beachcombing, bird-watching, gallery hopping and plenty of picture-taking.
Autumn in the Berkshire Hills

The Berkshire Back roads offers a mix of cultural riches, sweet farmland and mountain scenery © Denis Tangney Jr / Getty Images
Berkshire Back Roads 
Travel stats: 2-3 days; 31 miles 
These country roads offer a mix of cultural riches, sweet farmland and mountain scenery. In summer, enjoy music and dance in the open air; in autumn, indulge in apples straight from the orchard.
Pack a picnic of farm-fresh fruit and local cheese, spread your blanket on the lush green lawns, and settle in for an evening of world-class music under the stars. Or world-class dance.
Or Shakespeare. Or experimental theater. Indeed, for every day you spend hiking the hills and photographing the scenery, you can spend an evening taking in a cultural masterwork.
Mohawk Trail 
Travel stats: 2-3 days; 46 miles 
New England’s oldest scenic highway offers invigorating art and architecture, stimulating action and adventure, and spectacular mountain scenery – everything you need for a weekend getaway.
The road winds ever upward. Suddenly, around a bend, there’s a clearing in the forest and the landscape sprawls out in a colorful tapestry, yielding views across the valley and into neighboring states.
Welcome to the Western Summit of the Mohawk Trail, a 63-mile stretch of scenic byway, showing off raging rivers, idyllic farms and forest-covered mountains. Drivers, beware: it’s practically impossible to keep your eyes on the road.
You might also like:
How to road trip New England on a budget 
The ultimate New England fall foliage road trip  
Audiobooks to narrate your US road trip 
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JENNIFER BAR
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