New England adventures: best day trips from Boston 

In Boston, exploring is made effortless. Quaint historical towns and picturesque countryside are within easy driving distance from the city, making it an ideal base for exploring New England. Here, we reveal four of the best day trips in the region – and as a bonus, Cathay Pacific's Cathay members can enjoy discounted rates and earn Asia Miles when renting a car with us.  

The Berkshires  

This artsy oasis west of Boston is just a two-and-a-half-hour drive away, but it feels like another world. The pace here is slow and the roads winding; you’re likely to see as many farms as people. Start your day with a visit to Stockbridge, an enchanting town loved and immortalised by the artist Norman Rockwell. Grab a drink on the porch of the venerable Red Lion Inn , then visit the museum dedicated to Norman Rockwell to delight in some small-town Americana.   

The nearby town of Lenox is home to Tanglewood , the summer retreat of the Boston Symphony Orchestra, whose outdoor concerts are an annual rite of passage for New Englanders. Foodies should wander down Great Barrington’s Main Street to popular cheesemaker Rubiner’s ; browse, sample, and then repair to the shop’s cosy café, Rubi’s , for a gooey grilled cheese. For some deep relaxation, book a retreat at Kripalu , a haven for yoga, meditation, and healing arts that draws visitors from around the world. 

Cape Cod

No visit to Massachusetts is complete without a journey over the Bourne Bridge – or its twin, the Sagamore – to Cape Cod . This 105km peninsula is dotted with seaside towns, each with its own distinct character to suit every type of day-tripper.   

Swimmers should head to Orleans, where Nauset Beach provides fantastic surfing opportunities, a party atmosphere, and an abundance of food trucks. And if you’re feeling outdoorsy, visit Falmouth, home to the Shining Sea Bikeway. This flat 17km paved path — great for cycling, skating, or walking — winds past cranberry bogs and charming pebble beaches.  

When you’re ready to refuel, pop into Mexican bistro Añejo for a spicy margarita and lobster taquitos. Don’t forget to make a pit stop in Chatham for some great souvenirs, where you can find independent boutiques, galleries selling nautical art, and old antique shops. For beach décor, books, and quirky greeting cards, the Mayflower is an essential shopper’s pilgrimage. 

Towards the tip of Cape Cod, Wellfleet is home to a drive-in cinema where you can view much-loved classics, while Truro boasts mid-century architecture and dramatic dunes. Provincetown, at the very end of the peninsula, is the closest thing to a city in these parts, and Commercial Street is its liveliest thoroughfare. Sip frosé on the deck of popular eatery The Canteen , and sample sugar-coated malasadas, or fried dough balls, at the 87-year-old Provincetown Portuguese Bakery – visitors have been devouring these for generations.

Newport, Rhode Island  

This refined seaside town two hours’ south of Boston is known for its Gilded Age mansions that once belonged to New England’s most prominent families. You can admire them from Cliff Walk, a 5km oceanfront path open freely to the public. A key photo op? The Breakers , the former summer “cottage” of the illustrious Vanderbilt family, built in the late 1800s. These opulent estates also play host throughout the year to historical tours, seasonal dances, and wine tastings, so be sure to check out each venue’s calendar of events. 

Another great way to take in the views is by cruising along Ocean Drive, a 16km scenic coastal road that wends past pristine beaches and perfectly kept palatial homes and gardens. Craving sea breeze? Head to Sachuest Beach (known locally as Second Beach) for surfing and people-watching, or to the more secluded Third Beach for calmer waters. Lastly, if you’re in town in August, don’t miss the Newport Jazz Festival : musicians from all over the world flock to play at this lively three-day event.

Southern Maine

Salt air, craggy coastlines, and often icy cold Atlantic waters – New Englanders swear there’s nothing quite like it. Less than a two-hour drive northward from Boston, Maine is beloved for its gigantic lobster rolls (served either with warm drawn butter or mayonnaise) and utterly charming towns. Of these, Kennebunkport is probably the best-known: a picture-postcard village featuring adorable shops (pop into the Day Trip Society for a keepsake) and excellent restaurants (Mabel’s Lobster Claw, a quick stroll from the downtown area, serves an unbeatable blueberry pie).   

For a touch of whimsy, stop at Rococo Ice Cream , known for its outlandish flavours like goat’s cheese and whisky, before spreading out a blanket and nestling down at Mother’s Beach. On your way home, pull into Bob’s Clam Hut in Kittery for a classic Maine dinner: fried clams, onion rings, and a frappé.   

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