Gloucester's Fisherman's Memorial is a famous symbol of the Bay State's seafaring tradition. Fisherman's Memorial photo courtesy of the Massachusetts Office of Travel and Tourism

Things To Do on Cape Ann - Gloucester

1. Hammond Castle

Cape Ann Massachusetts might not seem like the right spot for a medieval castle. Built in the 1920's, Hammond Castle was designed to evoke the castles of England. Today it's home to a museum and hosts seasonal events for kids, like an Easter egg hunt in the Spring and Trick-or-Treat at Halloween. 

2. Fisherman's Memorial

Nothing symbolizes the history of Gloucester quite like this tribute to the seafarers that made Gloucester synonymous with fishing. "The Man at the Wheel" honors those lost at sea, including the crew of the Andrea Gail, made famous by the film The Perfect Storm.

3. Gloucester Harborwalk

The Gloucester Harborwalk is a (FREE) self-guided tour around the city. The 42 stops show families the major sites along the waterfront. Stage Fort Park on the harbor is also home to the annual Gloucester Waterfront Festival every Summer.

Things To Do on Cape Ann - Rockport

4. Bearskin Neck

A narrow peninsula lined with great eateries and shops, Bearskin Neck ends with a stumnning view of the ocean. This Rockport spot has been a favorite of artists for generations, demonstrated by the galleries and boutiques along Bearskin Neck.

5. Halibut Point State Park

Visiting tide pools can be a magical experience, where kids can see all kinds of aquatic creatures. Rockport's Halibut Point State Park is perfect for encountering some sea life. This state park also features hiking trails, picnic areas, and views of the coast that stretch all the way to Maine on a clear day.

6. The Paper House

One of the best roadside attractions in New England, the Paper House has drawn the attention of Cape Ann visitors for over a century. It's exactly what it claims to be, a house made out of newspaper, and even the furniture, including a piano, is also made of paper. It might be the most creative recycling program in history.

7. Thatcher Island

The Cape Ann Lighthouse Station on Thatcher Island features twin lighthouse towers. You have a great photo op from the shore. It's more fun to visit Thatcher Island (or nearby Straitsmouth Island) by booking a trip ("launch") from granite pier in Rockport. Note: reservations are required and children under 3 are not permitted on launches.

Things To Do on Cape Ann - Beaches

8. Good Harbor Beach - Gloucester

Gloucester's Good Harbor Beach offers plenty of space for warm-weather fun. At low tide, you can walk the sand bar to Salt Island. Good Harbor Beach fills upp quickly in the Summer (make parking reservations before you go).

9. Wingaersheek Beach - Gloucester

Wingaersheek Beach in Gloucester offers soft sand, tide pools, and gentle water, which is a bonus for younger visitors. Wingaersheek also requires parking reservations for non-residents during the high Summer season.

10. Half Moon Beach - Gloucester

Families looking for a quiet beach should hit the lovely, cozy Half Moon Beach. Gloucester's parking reservations also apply to Half Moon Beach.

11. Plum Cove Beach - Gloucester

Another small Gloucester beach fit for families, Plum Cove Beach's smaller dimensions help parents keep an eye on the little ones. Reservations are also required for parking.

12. Front Beach - Rockport

Close to much of Rockport's lodging and dining, Front Beach is close enough to town that visitors can leave the car at the hotel and stroll down to the sand.

13. Singing Beach - Manchester-by-the-Sea

Manchester-by-the-Sea has one of Cape Ann's most beautiful beaches. Non-resident parking is at a premium at this beautiful, broad stretch of sand and surf in Manchester, just southwest of Gloucester.

 
Find new friends with a cruise off of Cape Ann! Whale Watch Photo by Fred Goodwin for the Massachusetts Office of Travel and Tourism

Things To Do on Cape Ann - Family Fun

14. Whale Watches from Cape Ann

Cape Ann has many whale watching cruises departing from Gloucester. Humpbacks, finbacks, and minke whales are common sightings, and a whale watch is fun family excursion. High season for whale watching is from May to October, and Gloucester has three major whale-watching operations: Cape Ann Whale Watch, Seven Seas, and Captain Bill & Sons.

15. Dogtown

Up for a visit to Cape Ann's ghost, err, Dogtown? Once a colonial-era community, the area known as Dogtown Common straddles Gloucester and Rockport. None of the buildings are left, but a number of boulders and rock formations. Walking tours of thes woodland trails are offered by the Cape Ann Museum.

16. Cape Ann Museum

The region's history is on full display at the Cape Ann Museum. This museum features art and artifacts of life on Cape Ann. The museum's Green Campus features several historic buildings as well. Editor's Note: The Cape Ann Museum's main campus is undergoing extensive renovations, with a re-opening targeted for 2026. See the website for further details.

17. Rafes Chasm Park

This 10-acre park in Gloucester lets visitors climb over rocks (and through the chasm) to the ocean.

Things To Do on Cape Ann - Places To Eat

18. Azorean Restaurant - Gloucester

This eatery celebrates the cuisine of the vibrant Portuguese community that immigrated to Cape Ann. The delicacies of the Azores await, with seafood in the spotlight, as well as reliablekids' menu fare.

19. Seaport Grill - Gloucester

This waterfront Gloucester spot offers a higher-end spin on traditional faves, like lobster and fired seafood, as well as innovative meat and fish dishes.

20. Causeway Restaurant - Gloucester

This family-friendly spot has New Englanders' fried fish favorites, as well as pasta dishes, grilled entrees, and an extensive seafood menu.

21. The Lobster Pool - Rockport

Get amazing view of the sunset from this Rockport restaurant serving up lobster rolls, steamers, fried clams, and more.

22. Little Sister - Rockport

Had your fill of fish? Rockport's Little Sister Restaurant serves up burgers, dogs, and more casual fare during the warmer months. 

23. Woodman's of Essex - Essex

Whether the place invented the fried clam or not, Woodman's definitely stakes a claim to having perfected it. In addition to fried clamns and steamed lonbsters, Woodman's has an ice cream shop on site.

Things To Do on Cape Ann - Places To Stay

24. Beauport Hotel - Gloucester

The location of the Beauport cannot be beat. Right on the water and close to downtown Gloucester, the Beauport Hotel has a variety of rooms and suites, as well as a spectacular restaurant.

25. Atlantis Oceanfront Inn - Gloucester

The Atlantis Oceanfront Inn also has a number of different rooms, with full, queen, and king beds. Many of the rooms at the Atlantis have water views. and the inn's outdoor pool is certain to be a hit with the kids.