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Cape Ann, Mass.: The "other cape" is a seaside haven for history and art lovers

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It’s time to try the “other cape” — Cape Ann north of Boston — and its marquee destination towns, the historic fishing port of Gloucester and its picture-postcard neighbor, Rockport, a famous summer art colony that attracted big names like Edward Hopper, Winslow Homer and Childe Hassam. 

Great for:

Lovers of the sea, beach bums, history buffs, outdoor enthusiasts, seafood lovers, art lovers, families and couples.

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Rock Cliff at Good Harbor Beach in Gloucester

What to do:

Any list has to start with the beaches. The gorgeous Good Harbor Beach in Gloucester sits directly on the Atlantic. Rockport insiders love the diminutive but charming in-town Front Beach, while preservationists prefer the four-mile-long Crane Beach on Ipswich Bay in Ipswich. The best-kept secret? Off-the-radar and compact Wingaersheek Beach at the mouth of the Annisquam River has zero waves, but at low tide you can wade through ankle- and knee-deep water to walk far out on a sandbar.

In addition to galleries clustered on Rocky Neck in Gloucester and in Rockport center, art lovers should prioritize the Rockport Art Association & Museum and the Cape Ann Museum in Gloucester, whose collection features works by Gloucester’s own Fitz Henry Lane (you can see his house on Harbor Loop) and modern masters like Mardsen Hartley and Milton Avery.

The Shalin Liu Performance Center in Rockport, with its stunning glass rear wall looking over the harbor, features top-name jazz, folk and chamber music ensembles and will return to live concerts in July.

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A pianist practices at the Shalin Liu Performance Center

If you love the outdoors, Halibut Point State Park in Rockport offers a network of non-challenging trails, an abandoned granite quarry, and views all the way to the Isles of Shoals in New Hampshire and Mount Agamenticus in Maine.

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Hammond Castle

Fans of architecture shouldn’t miss Hammond Castle Museum in Gloucester, a medieval-style castle built in 1926 by inventor John Hays Hammond Jr., or the 2,100-acre seaside Crane Estate in Ipswich with its 59-room mansion.

The whale watch tours out of Gloucester are very popular, but don’t dismiss the appeal of a lighthouse cruise or tour of Gloucester Harbor, still very much a working fishing port and the setting for the film The Perfect Storm.

And for anyone staying in Rockport, or lucky enough to drive over and claim a parking space, it’s de rigueur to stroll around town and out to the end of Bearskin Neck in the evening, stopping for homemade ice cream, salt water taffy or candy at Tuck’s, or authentic strudel. Make sure to admire Motif #1, the red fishing shack that claims the honor of being one of the most painted buildings in the U.S. 

Where to stay:  The waterfront Beauport Hotel provides luxury lodgings on Gloucester Harbor and its own private beach, while the Blue Shutters Beachside Inn is both charming and located directly across the street from Good Harbor Beach. In Rockport, the true charm comes from staying within easy walking distance of town. The former Peg Leg has been transformed into the fresh and breezy Cove at Rockport, strategically across from Front Beach and next to the new Two Little Birds Eatery, while the Addison Choate across town is Rockport’s first boutique hotel with spa-like marble bathrooms, plush beds, the technology guests expect, and lots of charm.

Where to eat:

If you love seafood, you’ve come to the right place. Woodman’s of Essex is legendary for its fried whole belly clams, C.K. Pearl nearby takes a bit more of a fine-dining approach and is known for its oysters, and the Roy Moore Lobster Company on Bearskin Neck is literally a shack where you enjoy your lobster dinner out back, overlooking the harbor. Short & Main in Gloucester is the hot spot for artisan pizza, while nearby Tonno offers top-notch traditional and new Italian fare in a sophisticated setting. The 1606 Restaurant & Bar at the Beauport Hotel offers pure luxury and New England classics, while connoisseurs who love French-inspired comfort food and a romantic setting head to Duckworth’s in Gloucester.

If craft beer is your passion, Gloucester Brewing Company provides satisfaction. The Cape Ann food & drink cognoscenti also favor True North Ale Company in Ipswich and Riverwalk Brewing Co. in Newburyport.

Hidden gem:

Take a hike in the abandoned settlement Dogtown Common, said by some to be haunted. The Essex National Heritage Area website recounts that Dogtown was settled in 1693 because its inland location offered protection from pirates and enemy natives, and was abandoned in 1830 when it was safe to move settlements back to the seaside. The 3,600-acre expanse is criss-crossed by trails and known for its rock formations and boulders, notably the Whale’s Jaw. Legend says the area got its name from the dogs that provided companionship for women while their husbands fought in the American Revolution.

On the way:

Make a pit stop in Salem for lunch at the favorite local craft beer and pizza haven, Bambolina, visit the Peabody Essex Museum for art, maritime history and much more, and swing by The Witch House to brush up on the history and lore that give the town its unique cachet.

From Hartford: 2 hrs, 35 min / 159 miles

From New Haven: 2 hrs, 45 min / 174 miles

From New London: 2 hrs / 128 miles   

This article appears in the July 2021 issue of Connecticut MagazineYou can subscribe to Connecticut Magazine here, or find the current issue on sale hereSign up for our newsletter to get our latest and greatest content delivered right to your inbox. Have a question or comment? Email editor@connecticutmag.com. And follow us on Facebook and Instagram @connecticutmagazine and Twitter @connecticutmag.