Weekend in Gloucester

With pre-Revolutionary architecture and secluded beaches near Boston, this sprawling city is a rare combination of urban spirit and historic charm.

Gloucester: Local Culture

Photo: Tara Donne

Local Culture

Residents have long been drawn to the beautiful New England shore, with its colorful buoys painted in reds and oranges, its picturesque waterfront homes, and its panoramic vistas. And the rocky, oak tree-lined shores of Gloucester, Massachusetts, are no exception. But this is not a place consumed with being perfect for the sake of postcards: The lobster traps and rust-dappled fishing boats that you see in these deep blue Atlantic waters aren't just for show.

Gloucester is home to both America's oldest working seaport and the country's oldest working artists' colony, a quintessential cohabitation of art and commerce less than an hour's drive northeast of Boston.

Left: Boardwalk through the dunes at Wingaersheek Beach

Gloucester: Beaches

Photo: Tara Donne


There is a variety of sandy shores from which to choose:

Good Harbor Beach
In East Gloucester, this bustling beach is the place to be in the summer.

Wingaersheek Beach
Wingaersheek's shallow waters and gentle waves make this an ideal beach for kids.

Gray Beach
This quieter beach in Magnolia is a favorite spot for nature lovers. It’s populated with beach pea and beach rose, and an array of gulls.

Left: Sailing vessels in Smith Cove off Rocky Neck

Gloucester: Where to Eat and Drink

Photo: Tara Donne

Where to Eat and Drink

Sugar Magnolia's
Regulars wait in long lines for a taste of the sausage-stuffed Rocky Neck omelet and famous pineapple fritters. 112 Main Street, 978/281-5310 or sugarmags.com.

Latitude 43 and Alchemy
These sister restaurants serve fresh-caught local fish in everything from chowders and entrées to sushi in cozy, firelit spaces decorated with subtle maritime flair. Latitude 43: 25 Rogers Street, 978/281-0223 or latfortythree.com. Alchemy: 3 Duncan Street, 978/281-3997 or alchemybistro.com.

Cape Ann Brewing Company
Just down the street, the family-owned business serves specialty craft beer (brewed on site) and delicious fish-and-chips.11 Rogers Street, 978/282-7399 or capeannbrewing.com.

Left: One of the unique shops in East Gloucester

Gloucester: What to Do

Photo: Tara Donne

What to Do

Main Street downtown hosts funky coffee shops, antiques galleries, and indie bookstores. Gloucester is most active during the summer season, when the beaches, outdoor dining, citywide block parties, and Cape Ann Farmers' Market shine. But whale watches continue throughout the fall, and nature walks are popular year-round.

Left: The Bookstore of Gloucester on Main Street

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