15 Best Things to Do in Gloucester (MA)

Dubbed “America’s Oldest Seaport”, Gloucester was first settled by Europeans more than 400 years ago, and for all this time has been a center for the fishing industry.

From the 19th century, the moody seascapes at Cape Ann began to attract painters like Winslow Homer, and the longest-operating art colony in the United States can still be found here at Rocky Neck.

Modern Gloucester is a world-renowned summer vacation destination, and a favored place for day trips just over 30 miles from downtown Boston.

To go with a quaint downtown area, some of the best whale watching in the world, and authentic maritime heritage, Gloucester is blessed with white sandy beaches that have to be seen to be believed.

1. Good Harbor Beach

At places like Good Harbor Beach it’s easy to see what has brought artists to Gloucester for the last 170+ years.

This is most likely the best beach on the North Shore, with low rolling waves and a vast and gently pitching curve of white sand.

Just offshore is the granite mass of Salt Island, and the water recedes so far at low tide that you can walk to it across the sand. When the tide is up conditions are perfect for swimming, wading in the surf and bodyboarding.

As with Gloucester’s other premier beaches, Good Harbor Beach has lifeguards on duty from Memorial Day Weekend to Labor Day, and of course is open for you to swim at your own risk at other times of the year.

Although the beach is public, Gloucester has recently introduced an online parking reservation system for non-residents.

2. Fisherman’s Memorial Monument

A stately boulevard arcs around the harborfront on the west side of downtown Gloucester, and the promenade is an apt place for some contemplation.

Erected here in 1923 on Gloucester’s 3rd centennial is the Fisherman’s Memorial Monument, dedicated to the fisherman lost at sea.

This iconic work, by the English sculptor Leonard Craske (1880-1950), depicts a man in oilskins at the helm, evidently trying to steer through rough seas.

On a crescent of granite in front are plaques with the names of Gloucester fishermen lost at sea over the years, along with other drownings, in a list including women, children, dockworkers, engineers and vacationers.

3. Hammond Castle Museum

One interesting character from Gloucester was the inventor John Hays Hammond Jr. (1888-1965), remembered as “The Father of Remote Control”.

As well as being credited with more than 800 domestic and foreign patents, Hammond was an extensive traveler and had an eye for historic architecture.

In the 1920s he commissioned the Allen & Collens architectural firm to build the whimsical Hammond Castle as his home and laboratory.

Perched on a cliff overlooking the harbor, there are sections inspired by a 13th-century castle, a 13th-century French Gothic cathedral (Chartres) and a 15th-century chateau.

As well as being a place of work, this was all a fitting canvas for Hammond’s large collection of artifacts from Ancient Rome through the Renaissance.

Today this spellbinding complex is open to the public daily throughout the summer season, and on weekends in November and December. You can soak up the coastal views, see room after room of historic treasures and peruse Hammond’s many inventions.

4. Historic Downtown Gloucester

Tracing the Inner Harbor along the meandering Main St, Gloucester has a downtown area that is at once quaint and vibrant.

In a city famed for fishing you can bet that there are world-class seafood restaurants here, but that isn’t the limit of downtown’s dining selection, far from it.

Coffee shops and casual eateries are interspersed with antique stores, galleries, boutiques, museums and other cultural mainstays like the Cape Ann Community Cinema.

One way to get to grips with downtown’s present and past is on the Gloucester HarborWalk, a trail with 42 granite story posts throughout the historic center and along the waterfront.

If you’d like to witness Gloucester’s community spirit in full bloom be here for one of the Downtown Block Parties, shutting down Main Street for three summer nights, in July, August and September.

5. Whale Watching

Gloucester’s location, within miles of the Stellwagen Bank National Marine Sanctuary, and even closer to key feeding grounds, like Tillies Bank and Jeffreys Ledge, makes it the best place in Massachusetts, and one of the best places in the world for whale watching.

The most commonly sighted species are humpbacks, growing up to 60 feet, but you’ll also stand a great chance of seeing Minke whales (20 feet), and enormous fin whales, which are second only to blue whales in size, and have been known to reach more than 80 feet.

Sightings are pretty much guaranteed between May and October, and the main operators are Cape Ann Whale Watch (415 Main St) and 7 Seas Whale Watch (63 Rogers St).

6. Wingaersheek Beach

There’s an extraordinary public beach in western Gloucester on the northern coast of Cape Ann. Wingaersheek Beach traces the Annisquam River at its mouth for just over half a mile, giving it warm, sheltered waters that are perfect for children to splash in.

Halfway along the sandy shoreline there’s a set of granite outcrops that are easy to climb and have tidepools that kids will love to explore.

Meanwhile low tide exposes a huge sand bar that reaches out for hundreds of yards. The beach is patrolled by lifeguards every day from Memorial Day weekend to Labor Day, and as with Good Harbor Beach, parking reservations are required for non-residents.

7. Stage Fort Park

In the Western Harbor, Stage Fort Park is the site of a fishing outpost, established as early as 1623 by the Dorchester Fishing Company.

There was a fort here 1635 to 1898, and this was rebuilt for tourism in 1930, and armed with cannons, some of which are historic and some reproductions.

Stage Fort Park is now home to the Gloucester visitor center, and is a place for recreation, with a variety of sports facilities, dreamy harbor views and extensive beachfront.

One of the best public beaches in Gloucester Half Moon Beach, is right here, in a craggy and secluded cove, with shallow, rippling waters and lifeguards on duty daily from Memorial Day weekend to Labor Day.

8. Eastern Point Lighthouse

On a promontory on the east side of Gloucester Harbor there’s an active lighthouse, built in 1832 and occupied for a time by painter Winslow Homer in 1820.

Eastern Point Lighthouse is owned by the U.S. Coast Guard and is closed to the public, but it’s the location that makes a visit so worthwhile.

Shielding the entrance to the harbor here is a 2,250-foot granite jetty that is open to the public and has its own light at the end.

From here you can survey the harbor, look across the channel to grand residences like Hammond Castle, and gaze southwest to the Boston skyline.

9. Seafood

Gloucester’s connections to the fishing industry go back 400 years and are still strong, with an annual catch worth tens of millions of dollars, and several wholesalers based in the town.

You could not hope to find a better place to enjoy seafood direct from the Atlantic, and it’s such a part of Gloucester’s identity that the town has created the self-guided Seafood Trail.

This is a curated assortment of restaurants, museums and activities to help you get in touch with the industry in Gloucester.

For dining, a few spots running the gamut from high-end to laidback are Gloucester House Restaurant (63 Rogers St), The Dining Rooms at The Castle (141 Essex Ave), Turner’s Seafood Market & Fish n’ Chips Shoppe (4 Smith St), The Studio (51 Rocky Neck Ave), Causeway Restaurant (78 Essex Ave) and Seaport Grille (6 Rowe Sq).

10. Beauport, the Sleeper-McCann House

In 1907, one of the country’s first professional interior designers, Henry Davis Sleeper (1878-1934) built this Shingle Style house in Eastern Point as a place for entertaining and a showcase for his skills.

Beauport has a magical setting, posted on a rocky ledge overlooking the harbor, and appeared in numerous early home design and architecture publications in the first decades of the 20th century.

The interior is still suffused with Sleeper’s creative flair—no two of the 40 rooms are alike, and all are enriched with his massive collection of decorative arts, from china to folk art to colored glass.

Visiting Beauport you’ll get to know Sleeper, his housekeeper, Mary Wonson, and the many interesting characters who came through these doors.

11. Cape Ann Museum

Cape Ann has been closely associated with the arts since the 19th century.

Rocky Neck in Gloucester Harbor has been the site of an art colony for more than 170 years, bringing the likes of Edward Hopper and Winslow Homer, while in the mid-20th century the Folly Grove Designers, a group of block printers, rose to prominence in Gloucester.

This heritage is documented at the Cape Ann Museum, with works by Winslow Homer, Fitz Henry Lane, Cecilia Beaux, John Sloan, and a collection of sample books and display hangings by those printers.

The museum also covers other facets of the area’s history, with rich collections for granite quarrying, and the maritime and fishing industries.

12. Maritime Gloucester

On the harborfront by Gloucester Center you’ll come across the campus for a museum preserving the town’s rich maritime heritage.

Purchased in 2000, Maritime Gloucester is on a previously neglected industrial property, including forgotten treasures like the oldest operating Marine Railway in the United States.

You can cast your eye over several historic wooden boats, and the dory shop where these traditional fishing vessels are made by hand.

Requiring a small admission fee, there are gallery spaces dedicated to the 842-square-mile Stellwagen Bank National Marine Sanctuary, maritime science education, maritime art, as well as the outdoor Seapocket Aquarium, which has interactive touch tanks.

13. Ravenswood Park

For some quiet time you could escape to this 600-acre wooded property managed by the Trustees of Reservations.

Ravenswood Park was purchased as a patchwork of woodlots by the shipowner and merchant Samuel Sawyer (1815-1899), and was left to the town to be turned into a park when he died.

The reservation has more than ten miles of broad and mostly level carriage paths to travel, with some interesting changes in topography that give far-reaching views over Gloucester Harbor.

The landscape is dotted with granite boulders, reaching impressive sizes, and low-lying areas have swamp and vernal pools.

14. Cultural Center at Rocky Neck

The Rocky Neck Art Colony (RNAC) continues to thrive, and has an evocative home, at a Carpenter Gothic meetinghouse built in 1877.

This was purchased by the colony in 2012, and now has two levels of galleries, displaying exhibitions curated by the RNAC’s Cultural Center Exhibitions Committee.

There’s a tightly packed calendar of themed and solo exhibitions that tend to run for about five weeks, while the annual juried show for RNAC members takes place at the end of the year.

The unique building is also a stage for talks, workshops, concerts and a variety of other activities.

15. Fishermen’s Wives Memorial

For hundreds of years, Gloucester’s fishing community was held up by the resilient women who were given no choice but to remain on land and keep everything together.

In tribute, the Gloucester Fishermen’s Wives Association (GFWA) erected this affecting memorial as a counterpoint to the more famous Man At the Wheel, depicting a woman looking out to the entrance of the harbor, with a boy at her waist and an infant in her left arm.

This monument was dedicated in 2001, and stands at the north end of Stage Fort Park at 107 Western Ave.