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1. Holiday shopping on Main Street
A stroll down Gloucester’s Main Street is equal parts New England charm and fantastic shopping. There’s two bookstores, several boutiques, art galleries, a toy store, gourmet shops, and a few places that defy categorization (check out bakery/vintage shop/quirky home goods store Alexandra’s Bread to see what we mean). When your shopping bags are full, grab a hot beverage at the Lone Gull Coffee House or wander down a block for a sweet treat at Cake Ann.

2. Distillery tour and tasting
Ryan and Wood Distillery has been distilling small-batch spirits in Gloucester since 2006. Visit their facility to view the set-up, learn more about the process, and taste selections from their line-up of gins, rums, whiskeys, and vodkas. Then grab a bottle to enjoy at home. Details and contact information available on the distillery website.

3. History and heritage at the Cape Ann Museum
Focused on both art and history, the Cape Ann Museum aims to use its exhibitions to tell the story of Cape Ann. A walk through the museum offers a peek at the work of groundbreaking Folly Cove designers, a chance to immerse in Gloucester’s fishing industry, and the opportunity to wonder at the breathtaking paintings inspired by the region. Visit on Nov. 13 and you can take a walking tour of the area to see some of the houses that appear in the work of famed artist Edward Hopper.

Courtesy Cape Ann Museum

4. Look out at Eastern Point Light
At the outer tip of Gloucester’s Eastern Point, this classic New England lighthouse watches over the entrance to the country’s oldest seaport. Visitors can walk out the Dog Bar, a breakwater made from locally quarried granite that runs nearly a half mile out from the lighthouse. On one side, watch the goings on in the historic working waterfront, while on the other, views of the open ocean stretch to the horizon.

5. Bundle up on the beach
The weather might be too cold for bathing suits, but a walk on the beach is delightful any time of year. Watch waves roll in at Good Harbor Beach, scramble over rocks at Wingaersheek Beach, or take in a vibrant sunset at Niles Beach. Just don’t forget your hat and scarf.

6. Hammond Castle Museum
Built by radio control pioneer John Hays Hammond Jr., Hammond Castle combines elements of medieval and Renaissance architecture to create a bit of fairy tale charm in Gloucester. Visitors can wander the grounds free of charge, or pay admission to tour the eclectic interior. From mid-November on, rooms will be decorated for the holidays by local designers, so this is the ideal time of year to be charmed by the castle. Details are available at the museum website.

7. A Ravenswood ramble
At Ravenswood, 10 miles of trails meander through 600 wooded acres, for a woodsy walk just moments from the sea. Studded with glacial boulders, the Ledge Hill Trail is a fun place for kids to clamber (and includes a scenic overlook of Gloucester Harbor), while the wide, largely level Old Salem Road is perfect for a low-impact stroll. Ravenswood is very dog-friendly, so bring along your canine companions.

Ravenswood / Photo courtesy of The Trustees of Reservations

8. Live music
Gloucester’s vibrant arts scene includes a healthy population of local musicians who perform regularly at local venues. Two of your best bets are The Rhumb Line, a casual neighborhood pub that hosts rock, reggae, blues, and acoustic performers almost every night of the week, and Minglewood Harborside, a popular restaurant where you can enjoy sushi, burgers, and creative tavern food while listening to live bands.

9. Dine in an igloo
When COVID shut down indoor dining and winter made outdoor seating a chilly proposition, the folks at Cape Ann Marina’s Mile Marker One restaurant got creative: They built heated plastic igloos on their deck, allowing diners to enjoy breakfast, lunch, or dinner in cozy, well-ventilated privacy. And, as of the first weekend of November, the igloos are back. Visit the marina’s website for more information, to view menus, or to make reservations.

10. Feast on seafood
It would be a shame to visit the country’s oldest fishing community and not try some of its wares. And there are plenty of ways to do so. Indulge in a heaping platter of fried clams at the Causeway Restaurant, sample the lobster and cod combo at the Seaport Grille, nibble salted cod fish cakes with Portuguese spices at the Azorean Restaurant and Bar, or visit Tonno for a simple-yet-delicious meal of tuna with white beans and escarole.