Things to do in Gloucester

Gloucester is a special place for both of us and we’re honored to share it with our guests.

Find a few of our favorite things below, and linked on this shared Google map.

Milton Avery “Bridge to the Sea”

Take a dip in the ocean

Boasting the best beaches in the world*, a trip to Gloucester is incomplete without a beach day. The water is at its warmest in September, so we hope you’ll enjoy a dip!

Good Harbor Beach
Conveniently located downtown, our favorite beach is also everyone else’s, so while reservations/fees are not required after Labor Day, it may still be crowded.

Plum Cove Beach
A go-to for a quick dip close to Emma’s parents’ house, Plum Cove is a small beach off the beaten path in Lanesville. (Note: Like most places in Gloucester, parking is limited.)

Wingaersheek Beach
A bit of a drive, this beauty on the other side of the cape is another popular spot that won’t disappoint!

( * according to Emma)

Edward Hopper “Gloucester”

See some art

Gloucester has a rich history in art, and many artists, from Stuart Davis to Marsden Hartley to Edward Hopper, have spent time creating here.

Unfortunately, the Cape Ann Museum (where Emma’s mom was the director for many years) is closed for renovations this year. However, if you are joining us for the welcome gathering Friday night at CAM Green, this will give you a little flavor of the museum collection.

More art can be found at:

  • Beauport, Sleeper-McCann House

  • The Cultural Center at Rocky Neck

  • The Salted Cod (gallery and wine bar)

  • Jane Deering Gallery

  • Matthew Swift Gallery

  • COSMOS Gallery

  • See the Man at the Wheel statue on the Boulevard

Aino Clarke “Lobsters II”

Eat, Drink and Shop

Short & Main: For award-winning wood-fired pizza, oysters and cocktails. Get there right when they open or make a reservation.

Virgilio’s Bakery: If you’re craving a classic Italian sandwich (one of George Clooney’s favorites while filming The Perfect Storm).

Holy Cow Ice Cream: A childhood favorite of Emma’s, serving homemade ice cream (regular and vegan).

Carl’s Cones: Another great option for a cone.

Caffe Sicilia: Old-school spot for espresso and Italian baked goods.

Lone Gull Coffee House: Popular local hang on Main St.

Source Bakery: For delicious pastries, coffee and breakfast sandwiches.

Sebastian’s Pizza: A Chandler family favorite. Pies and slices.

Lobster Pool: A casual, seafood spot on the north side of the cape with great sunset views. If you do venture over to this part of Gloucester, consider checking out nearby Halibut Point State Park, where you can take in scenic views (on a clear day, you can see Maine!) and explore the remnants of Gloucester’s quarrying industry.

Beauport Hotel lobby: For drinks and a view of the harbor.

A stroll down Main St. will take you past our favorite shops: Bananas Vintage, The Bookstore, Mystery Train Records and Cape Ann Olive Oil Co.

Winslow Homer “Gloucester Harbor”

Go to sea

Schooner Sail
Take a harbor cruise on a schooner! The Thomas E. Lannon or the Adventure schooner are great options, both leaving from downtown.

Whale Watch
Gloucester is known for fishing, but we also have whales! Go on a tour with Cape Ann Whale Watch or 7 Seas Whale Watch, which both leave from downtown.

Maritime Gloucester Museum
Learn about the sea, and Gloucester’s maritime history, from land!