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Whale Watch

Whale watching is a must. Choose from among three local companies: 

Cape Ann, 415 Main Street, 978-283-5110,

7 Seas Whale Watch Company, 63 Rogers Street, 978-283-1776,

Capt. Bill & Sons24 Harbor Loop, 800-339-4253,


Beauport Princess

Book a brunch, lunch, or dinner cruise aboard the Beauport Princess.

6 Rowe Square, 978-865-3210,


Cape Ann Museum

Visitors immerse themselves in the region’s art and history at Cape Ann Museum. 

27 Pleasant Street, 978-283-0455,


Ravenswood Park

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.

481 Western Ave., 978-281-8400,


Eastern Point

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.

24 Hough Ave., 978-281-9785,


Gloucester Stage Company

Staging exciting new professional plays in a quaint seaside theater.

267 E. Main Street, 978-281-4433,


Seaport Grille

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.

6 Rowe Square, 978-282-9799,


The Market Restaurant

Enjoy a farm-to-table feast overlooking the Annisquam River.

33 River Road, 978-282-0700,



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.

9 Dale Ave., 978-281-9700,


Rocky Neck

An artists’ colony since the 1800s, Rocky Neck combines colorful galleries, local artists’ studios, and popular restaurants.

6 Wonson Street, 978-515-7004,


Good Harbor Beach

With its white sand, accessible island, and tidal creek, Good Harbor Beach is one of the city’s most popular spots.

Thatcher Road, 978-281-9785,


Maritime Gloucester

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.

23 Harbor Loop, 978-281-0470,


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


Wingaersheek Beach

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.


Dogtown Common

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.

Access point is off of Cherry Street.


Hammond Castle

Medieval-style Hammond Castle lets visitors explore the (possibly haunted?) home and oceanfront grounds of inventor John Hays Hammond, Jr.

80 Hesperus Ave., 978-283-2080,


Beauport, the Sleeper-McCann House

Gives visitors a glimpse into architectural and interior design history.

75 Eastern Point Blvd., 978-283-0800,


Ryan & Wood Distilleries

Tour Ryan and Wood Distilleries to see the process behind the company’s critically acclaimed, rum, vodka, whiskey, and gin.

15 Great Republic Drive, 978-281-2282,


Latitude 43 and Minglewood Tavern

Serving up creative takes on local seafood and pub fare with waterfront views.

25 Rogers Street, 978-281-0223,


Willow Rest

The perfect stop for local produce, gourmet snacks, fresh-baked treats, and some of the best sandwiches on the North Shore.

1 Holly Street, 978-283-2417,


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.

76 Prospect Street, 978-282-1455,


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


Beauport Hotel

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.

55 Commercial Street, 978-282-0008,


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.

75 Essex Ave., 978-283-2122,


Learn more about Gloucester here