Escape to a Tranquil Massachusetts Town for a Quiet Weekend Getaway

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Colorful portside buildings at sunset

Travel Guides Weekend Getaways

 Melanie Carden



New England has a near-endless supply of idyllic seaside settings. Unfortunately, sometimes that also includes large crowds (we’re looking at you and your big crowds, Cape Cod). So, in addition to being strategic with the calendar and avoiding popular vacation spots at the height of summer, there are also some year-round opportunities hiding in plain sight.

Of course, people flock to Boston, Massachusetts, for its rich history, famous clam chowder, and vibrant sports culture, but the state also offers quieter getaways. Nestled along the state’s shoreline, you’ll find small towns and hamlets with that Main Street, USA, feel that many of us long for these days. These cozy communities offer small shops, art galleries, mom-and-pop businesses, and eclectic coffee houses and eateries.

One such town, Rockport, is located at the furthest end of the Cape Ann peninsula, and a shoreline drive is the best way to kick off your weekend getaway. Rockport is just an hour from Boston, and the drive will take you through some of the state’s famous movie locations. You’ll pass through Manchester-by-the-Sea, made famous by the movie of the same name starring Ben Affleck, plus Gloucester, where “Perfect Storm” was filmed, starring George Clooney and Mark Wahlberg (via Discover Gloucester).

Visit America’s most painted building

Motif No. 1 in Rockport, Massachusetts



Bob Pool/Shutterstock

After you meander into town, Rockport’s charm is as plentiful as the lobster traps scattered about. And if quietude is the agenda, check into the historic and picturesque Emerson Inn, which sits along a craggy nook between Halibut Point and Bearskin Neck. Sit on the veranda and watch the waves crash against the rocks, knowing you’re among the many travelers who’ve sought relaxation at this property — for 150 years.

Once settled, it’s easy to plan a weekend of crowd-free downtime in Rockport, known for its beautiful rocky shoreline, quaint harbor, and active artist colony. The town’s website boasts over 30 art galleries, in addition to the Rockport Art Association and Museum, the Shalin Liu performing arts center, and (in true New Englander fashion) countless open-air festivals from May right on through December.

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But one of the most artistic elements in Rockport is a little red shack, known the world over as Motif No. 1. An odd name for a harborside hut, but it’s known as America’s most-painted building, named (via Rockport USA) — in jest — by illustrator Lester Hornby. He was teaching in Rockport when yet another student presented a drawing of the idyllic shack, and he proclaimed, “What? Motif No. 1, again!”

Rockport serves up lobster rolls and classic New England charm

Roy Moore Lobster Co. storefront

Wangkun Jia/Shutterstock

So, if you’re an art enthusiast, the many galleries and exhibitions might be how you spend your weekend getaway in Rockport. But there’s so much more, according to Rockport resident of four decades, Patricia Brown, who told Boston.com that her hometown is “Massachusetts at its best.” One of her top suggestions for visitors is to have a lobster roll at the iconic Roy Moore Lobster Co., a 104-year-old culinary pillar of the seaside town, as described by North Shore Magazine.

Ride that ocean-themed wave on over to the Twin Lighthouses of Straitsmouth and Thacher Islands, or take a shoreline hike at Halibut Point State Park. For longer outings, consider a local boat tour — Downeast Yacht Tours offers private yacht excursions departing from Rockport, or book a day of whale watching with nearby 7 Seas Whale Watch. Or you may fancy yourself as more of a captain. If so, North Shore Adventure offers kayak and paddleboarding tours, including outings dedicated to viewing seals in their natural habitats.

And, of course, leave time for Rockport’s charming shops — rows of dreamy coastal storefronts, perfectly weatherworn and oh-so-welcoming. Leave time for The Pewter Shop — a Rockport gem of 87 years — and Bearskin Neck Country Store, of course.

Dave Pennells

By Dave Pennells

Dave Pennells, MS, has contributed his expertise as a career consultant and training specialist across various fields for over 15 years. At City University of Seattle, he offers personal career counseling and conducts workshops focused on practical job search techniques, resume creation, and interview skills. With a Master of Science in Counseling, Pennells specializes in career consulting, conducting career assessments, guiding career transitions, and providing outplacement services. Her professional experience spans multiple sectors, including banking, retail, airlines, non-profit organizations, and the aerospace industry. Additionally, since 2001, he has been actively involved with the Career Development Association of Australia.