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Discover New England Self-Drive

Beauty abound

An anti-clockwise tour around the highlights of New England, visiting parts of Massachusetts, Maine, Vermont, and Rhode Island, bookended with stays in Boston.

This itinerary shows you most of New England’s main highlights. Stop off in the Berkshires, a popular holiday haunt for Boston’s and New York’s elite since the 1800s; discover glorious mountains in New Hampshire and green scenery in Vermont; and savour stunning sea views in Newport, Rhode Island.

Tour type Self-drive

Visiting Boston, Massachusetts; Kennebunkport, Maine; Bar Harbor, Maine; Jackson, New Hampshire; Vergennes, Vermont; Stockbridge, Massachusetts; Newport, Rhode Island; Falmouth, Massachusetts

Recommended itinerary

Boston

Welcome to Massachusetts

Orientate yourself with the city by following the Freedom Trail, a series of 16 historic sights that tell Boston’s incredible story. You could also take a wander around the beautiful grounds and museums at Harvard University or catch the Red Sox in action at Fenway Park.

Kennebunkport

Wild beaches and whoopie pies

Pick up your hire car and drive 100 miles north. Here, you can find a patch of the exceptionally beautiful Goose Rocks Beach to call your own, peruse the collection of streetcars at the Seashore Trolley Museum, and ride a vintage trolley. It’s a renowned foodie spot famous for its soft and cakey whoopie pies.

Bar Harbor

Beach chic in Arcadia

It might not be the fastest route to Bar Harbor, but if you follow Route 1, you’ll pass through some lovely towns like Waldoboro and Rockland and get fabulous ocean views. When you arrive, stretch your legs on Bar Harbor’s Shore Path, which provides fantastic views of the harbour and the mountains. Perhaps you’ll hike in Acadia National Park or take a whale-watching tour before returning for dinner. You’ll find everything from seafood shacks to fine-dining restaurants.

Jackson

The White Mountains await

On your drive to Jackson, you’ll cross the state border from Maine to New Hampshire for some time in the White Mountains. This is a particularly resplendent area when it's ablaze with colour in the autumn, but it's just as pretty in other months. Try canoeing deep into the scenery or following miles of hiking trails that crisscross the terrain.

Vergennes

Explore Lake Champlain

Take the scenic Kancamagus Highway on your drive to Vergennes, crossing into Vermont. When you arrive, there’s a small downtown area to explore. Still, most find themselves here for incredible outdoor adventures, whether you prefer hiking and biking or watery escapades like kayaking and sailing on Lake Champlain.

Stockbridge

Into the Berkshires

Drive south back into Massachusetts to the Berkshires, where quaint, storybook-style New England inns have a backdrop of mountains and forests. Spend your days exploring food markets, orchards, and breweries, or up the ante on ziplines and white-water rapids.

Newport

Beside the seaside

Rhode Island is the smallest state in the USA by area and home to the sailing capital of New England, Newport. Orientate yourself by following the 3.5-mile Cliff Walk and looking at some of the impressive Newport Mansions from the Gilded Age.

Falmouth

To Cape Cod

From your base in Falmouth, you can explore Cape Cod or even take a ferry to the gorgeous islands of Martha’s Vineyard or Nantucket for the day. You can also go whale watching, cycle the Cape Cod Rail Trail past cranberry bogs and salt marshes, or relax at the beach and enjoy the ocean breeze.

Boston

Back to the city

Your circular tour of New England is complete when you return to Boston, a final exclamation mark on an incredible trip to a picture-perfect slice of the USA. Finish your holiday with a shopping trip on Newbury Street and a fabulous dinner in Boston’s North End before your international flight takes you back to the UK.

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