Gloucester Must-Do List
Items for your Gloucester Itinerary
Whale watching is a must. Choose from among three local companies:
Book a brunch, lunch, or dinner cruise aboard the Beauport Princess.
Cape Ann Museum
Visitors immerse themselves in the region’s art and history at Cape Ann Museum.
Meander Ravenswood Park, whose 600 wooded acres and 10 miles of moderately difficult trails are perfect for family hikes, dog walking, and even cross-country skiing come winter.
Drive to the end of Eastern Point to stroll the local Audubon Sanctuary, check out the scenic lighthouse, and venture out on the nearly half-mile granite breakwater.
Stage Fort Park
Offering a playground, dog park, small beach, weekly farmers’ market, picnic areas, playing fields, and gorgeous views of Gloucester Harbor.
Gloucester Stage Company
Staging exciting new professional plays in a quaint seaside theater.
Because great seafood is a Gloucester must, head to the Seaport Grille for a plate of its famous fried clams or delicious lobster roll—and great cocktails.
The Market Restaurant
Enjoy a farm-to-table feast overlooking the Annisquam River.
The 1.2-mile HarborWalk provides a free self-guided walking trail that leads visitors on a tour through Gloucester’s history, working waterfront, art, and culture.
An artists’ colony since the 1800s, Rocky Neck combines colorful galleries, local artists’ studios, and popular restaurants.
Good Harbor Beach
With its white sand, accessible island, and tidal creek, Good Harbor Beach is one of the city’s most popular spots.
A working waterfront museum featuring a sea creature touch tank, a workshop where a local craftsman builds wooden dories, and voyages on a traditionally constructed schooner.
Pleasant Street Tea Co.
Serving up a wide menu of coffee, tea, sandwiches, and salads alongside unparalleled people watching.
7 Pleasant Street, 978-283-3933
On the western edge of town, Wingaersheek Beach has plenty of space, excellent swimming, and rocky outcroppings for the kids to explore.
Access point located at the end of Atlantic Street off of Route 133 and Concord Street.
Gloucester Fisherman’s Memorial
Take a walk along Stacy Boulevard to visit the the famous “Man at the Wheel” statue and watch boats sailing in and out of the harbor.
An abandoned 17th-century settlement, Dogtown Common is known for miles of nature trails, dozens of boulders carved with inspirational sayings, and dugouts that once served as cellars for long-disappeared houses.
Medieval-style Hammond Castle lets visitors explore the (possibly haunted?) home and oceanfront grounds of inventor John Hays Hammond, Jr.
Beauport, the Sleeper-McCann House
Gives visitors a glimpse into architectural and interior design history.
Ryan & Wood Distilleries
Tour Ryan and Wood Distilleries to see the process behind the company’s critically acclaimed, rum, vodka, whiskey, and gin.
Latitude 43 and Minglewood Tavern
Serving up creative takes on local seafood and pub fare with waterfront views.
The perfect stop for local produce, gourmet snacks, fresh-baked treats, and some of the best sandwiches on the North Shore.
Savour Wine and Cheese
Offers complimentary tastings of 20 small-production wines. The shop also stocks exceptional cheeses from around the world as well as gourmet items.
The Harbor Room
With traditional New England detailing, The Harbor Room offers a beautiful place for a wedding or bridal shower.
8 Norwood Ct., 978-729-8286
Designed by Olson Lewis + Architects and built by Windover Construction, this 94-room luxury hotel on Gloucester’s waterfront is the latest venture by the Beauport Hospitality Group. Open this June, it is the finest hotel on Boston’s North Shore.
Cape Ann Marina Resort
Offering both short- and long-term dockage. The hotel treats guests to rooms on the water, or overlooking the salt marshes, and its Mile Marker One Restaurant and Bar features traditional New England fare in a nautically inspired setting.
Learn more about Gloucester here