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Maybe you only think of visiting Gloucester, the historic city on Cape Ann, during the summer. And while the town has more than its share of beautiful beaches, it provides endless reasons to come here all year long. Many prefer the fall, when the roads and restaurants are less crowded and autumn foliage provides a beautiful backdrop for history, culture, shopping, and dining.


Check in at the Beauport Hotel, Gloucester’s new 94-room seaside luxury hotel overlooking the harbor. Each room provides stellar views, whether of the water or the city. The nautical décor manages not to look cheesy, and locals seek out their restaurant and bar.

For less of a splurge, stay at the Harborview Inn in the heart of the Boulevard, a street that the city of Gloucester turned into an ocean-facing park in the 1930s, when it removed all the houses on the water side. Here stands the famous “Man at the Wheel,” also known as the Gloucester Fisherman’s Memorial. Everyone comes here to walk their dog or to stroll with friends; you’ll find no better place for people-, dog-, or boat-watching.

After you’ve checked in to your accommodations, head to Plum Cove Beach to watch the sunset. Located on Washington Street in the northern part of the city, this small, horseshoe-shaped beach faces west. The view of Ipswich Bay is said to resemble that of the Gulf of Naples, but surely the Neapolitans have no better view of the setting sun.

For dinner, try The Azorean, where local businessman Deo Braga has recreated the look and feel of his native Portuguese islands. A wide-ranging menu offers such Azorean delights as octopus and fava beans, as well as steaks and burgers. Prices are reasonable and the ambiance is friendly and unpretentious.

For live music after dinner, pop around the corner to The Rhumb Line. The local watering hole offers live music every night, as well as any after-dinner drink you might crave.


The local breakfast place is Lee’s, at the beginning of East Main Street. They serve breakfast until they close at about 1 p.m. Whether you like pancakes, eggs, biscuits and gravy, waffles, or that local specialty, fish cakes, Lee’s has them. Plus, endless mugs of coffee, of course.

After breakfast, drive to the end of Eastern Point, park in the small dirt parking lot, and go for a walk on the Dog Bar Breakwater. Heading a half mile into the middle of Gloucester Harbor, it provides glorious views of the city and the harbor while its massive granite boulders make for delightful walking or skipping.

Grab a sandwich at Virgilio’s, on the historic west end of Main Street. “Bread of the Fishermen” is what the family calls their product. One specialty is a St. Joseph’s sandwich, in which Italian cold cuts are layered in a crusty roll, seasoned with oil and herbs.

After lunch, tour the Cape Ann Museum. Here, everything you want to know about Gloucester’s rich maritime and art history are on display. Especially wonderful are the paintings by local luminary Fitz Henry Lane and the blockprints of a delightful artisan collective, the Folly Cove Designers.

When you leave the museum, stroll down Main Street, stopping in at Local Colors, an artists’ collective, Bananas, a vintage shop with attitude and edge, The Bookstore, a rare example of the endangered independent local bookstore, and Turtle Alley, for a sweet treat. Get off your feet at Caffé Sicilia and have a cannoli.

Saturday night dinner is special, indeed, at Duckworth’s Bistrot. Gloucester’s temple to five-star dining is located in a small storefront in East Gloucester Square. Classically trained chef Ken Duckworth cooks as if each meal is his personal way to make the world a better place. The ambiance is informal, the food is seasonal and local. However, you will need a reservation—Duckworth’s is always full.


For breakfast, cruise the buffet at the Beauport Hotel, before heading out for a brisk walk in Ravenswood Park, a nature preserve managed by the Trustees of Reservations. The park boasts more than 10 miles of carriage paths and trails and offers the perfect place to take in the area’s natural beauty.

After your nature walk, drive Route 127 around the perimeter of Cape Ann and through Gloucester’s neighborhoods, including East Gloucester, Bass Rocks, Lanesville, Bay View, and Annisquam. You will see that Gloucester is an island, a large part of what makes this city on Cape Ann so special.

Before leaving this seafaring city, treat yourself to an early dinner at Short & Main, a small restaurant with some of the best food on the North Shore. The well-curated menu offers crudi, small plates, to-die-for pizza, perfect salads, as well as a pasta and a meat dish. The ingredients are sourced locally and the chefs were trained at Chez Panisse—need I say more?