Top 15 Attractions and Activities in Gloucester, MA

Dubbed “America’s Oldest Seaport”, Gloucester was first settled by Europeans more than 400 years ago and has since served as a significant center for the fishing industry.

Beginning in the 19th century, the evocative seascapes of Cape Ann began to attract artists such as Winslow Homer, and today, the longest-operating art colony in the United States can still be found here at Rocky Neck.

Contemporary Gloucester is recognized as an internationally sought-after summer vacation destination, favored for day trips that are just over 30 miles from downtown Boston.

In addition to its charming downtown area, Gloucester offers exceptional whale watching opportunities and a rich maritime heritage. Moreover, it boasts stunning white sandy beaches that must be experienced firsthand.

1. Good Harbor Beach

At locations like Good Harbor Beach, it is evident why artists have been drawn to Gloucester for over 170 years.

This beach is arguably the finest on the North Shore, featuring gently rolling waves and a wide, smoothly sloping expanse of white sand.

Offshore, the granite formation of Salt Island is visible, and during low tide, visitors can walk across the sand to reach it. When the tide rises, the conditions are ideal for swimming, wading in the surf, and bodyboarding.

Like Gloucester’s other premier beaches, Good Harbor Beach employs lifeguards from Memorial Day Weekend through Labor Day, and guests are permitted to swim at their own risk during other times of the year.

Although open to the public, Gloucester has recently implemented an online parking reservation system for non-residents.

2. Fisherman’s Memorial Monument

A picturesque boulevard curves around the harborfront on the west side of downtown Gloucester, providing a fitting location for contemplation.

Established in 1923 in celebration of Gloucester’s third centennial, the Fisherman’s Memorial Monument pays tribute to fishermen lost at sea.

This iconic structure, created by English sculptor Leonard Craske (1880-1950), depicts a man in oilskins at the helm, apparently navigating through tumultuous waters.

On a crescent of granite in front, plaques are inscribed with the names of Gloucester fishermen who have perished at sea over the years, including women, children, dockworkers, engineers, and vacationers.

3. Hammond Castle Museum

One intriguing figure from Gloucester was the inventor John Hays Hammond Jr. (1888-1965), who is often referred to as “The Father of Remote Control”.

Beyond being credited with over 800 domestic and international patents, Hammond was an avid traveler with a keen interest in historical architecture.

In the 1920s, he commissioned the Allen & Collens architectural firm to design the whimsical Hammond Castle, which served as both his home and laboratory.

This castle, perched on a cliff with views of the harbor, incorporates elements inspired by a 13th-century castle, a 13th-century French Gothic cathedral (Chartres), and a 15th-century chateau.

In addition to being a workspace, this enchanting site housed Hammond’s extensive collection of artifacts spanning from Ancient Rome to the Renaissance.

Today, this captivating complex is accessible to the public daily during the summer season and on weekends during November and December. Visitors can enjoy picturesque coastal views, explore room after room of historic treasures, and learn about Hammond’s various inventions.

4. Historic Downtown Gloucester

Tracing the Inner Harbor along the winding Main St, downtown Gloucester presents a charming yet vibrant atmosphere.

In a city renowned for its fishing industry, visitors will find numerous exceptional seafood restaurants; however, the dining options extend well beyond seafood alone.

Coffee shops and casual dining establishments are intermingled with antique stores, art galleries, boutiques, museums, and other cultural landmarks, such as the Cape Ann Community Cinema.

A comprehensive way to explore downtown’s history is via the Gloucester HarborWalk, a trail featuring 42 granite story posts throughout the historic center and along the waterfront.

To experience Gloucester’s community spirit, one should attend one of the Downtown Block Parties, which temporarily close Main Street for three summer evenings in July, August, and September.

5. Whale Watching

Gloucester’s geographic location, just a few miles from the Stellwagen Bank National Marine Sanctuary, and even nearer to critical feeding grounds like Tillies Bank and Jeffreys Ledge, make it an optimal location in Massachusetts for whale watching.

The most frequently sighted species include humpback whales, which can grow up to 60 feet long, along with the smaller Minke whales (approximately 20 feet) and the impressive fin whales, known for being the second-largest species after blue whales, reaching lengths of over 80 feet.

Whale sightings are nearly assured between May and October, with primary operators including Cape Ann Whale Watch (415 Main St) and 7 Seas Whale Watch (63 Rogers St).

6. Wingaersheek Beach

Wingaersheek Beach, located in western Gloucester along the northern coast of Cape Ann, is an exceptional public beach.

This beach follows the Annisquam River at its mouth for slightly over half a mile, offering warm, sheltered waters that are ideal for children.

Along the sandy shoreline, there are rocky outcrops that are easily accessible for climbing, as well as tidepools for children to explore.

At low tide, a vast sandbar emerges, extending hundreds of yards into the water. Lifeguards patrol the beach daily from Memorial Day weekend to Labor Day, and similar to Good Harbor Beach, parking reservations are necessary for non-residents.

7. Stage Fort Park

Stage Fort Park, situated at the Western Harbor, was originally established as a fishing outpost in 1623 by the Dorchester Fishing Company.

The area housed a fort from 1635 to 1898, which was rebuilt for tourism in 1930 and equipped with cannons, some historic and others replicas.

Today, Stage Fort Park is home to the Gloucester visitor center and serves as a recreational space, featuring various sports facilities, picturesque harbor views, and extensive beachfront.

One of the best public beaches in Gloucester, Half Moon Beach, is located here in a secluded cove, offering shallow, gentle waters and lifeguard services daily from Memorial Day weekend to Labor Day.

8. Eastern Point Lighthouse

Perched on a promontory on the eastern side of Gloucester Harbor, this active lighthouse was constructed in 1832 and was once occupied by painter Winslow Homer in 1820.

Owned by the U.S. Coast Guard, Eastern Point Lighthouse is not open to the public; however, its location makes it a worthwhile destination.

A 2,250-foot granite jetty, which shelters the harbor entrance, is accessible to the public and features its own light at the end.

From this vantage point, visitors can survey the harbor, gaze across the channel towards notable residences such as Hammond Castle, and view the skyline of Boston to the southwest.

9. Seafood

Gloucester’s longstanding ties to the fishing industry date back 400 years and remain strong today, with an annual catch valued at tens of millions of dollars and several wholesalers operating in the town.

There is no finer place to relish seafood freshly sourced from the Atlantic Ocean, a core aspect of Gloucester’s identity, leading to the establishment of the self-guided Seafood Trail.

This curated selection includes restaurants, museums, and activities designed to connect visitors with the local fishing community.

Dining options range from upscale to casual, including 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, Henry Davis Sleeper (1878-1934), one of the nation’s premier interior designers, constructed this Shingle Style residence in Eastern Point as a venue for entertaining and showcasing his design talents.

Beauport boasts a stunning location, set on a rocky ledge overlooking the harbor, and has been featured in numerous early home design and architecture publications during the early 20th century.

The interior retains Sleeper’s artistic essence; no two of the 40 rooms are alike, each enriched by his extensive collection of decorative arts, which includes items ranging from china to folk art to colored glass.

A visit to Beauport provides insight into Sleeper, his housekeeper Mary Wonson, and the array of intriguing individuals who have passed through these doors.

11. Cape Ann Museum

Since the 19th century, Cape Ann has maintained a close association with the arts.

Rocky Neck in Gloucester Harbor has been home to an art colony for more than 170 years, attracting notable figures such as Edward Hopper and Winslow Homer. In the mid-20th century, the Folly Grove Designers, a collective of block printers, gained prominence in Gloucester.

This artistic heritage is showcased at the Cape Ann Museum, featuring 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 explores various facets of the area’s history, showcasing rich collections related to granite quarrying, as well as the maritime and fishing industries.

12. Maritime Gloucester

Located along the harborfront near Gloucester Center, Maritime Gloucester serves as a museum dedicated to preserving the town’s rich maritime heritage.

Acquired in 2000, Maritime Gloucester occupies a previously neglected industrial site, which hosts treasures such as the oldest operating Marine Railway in the United States.

Visitors can view several historic wooden boats, as well as the dory shop where traditional fishing vessels are crafted by hand.

With a modest admission fee, guests can explore gallery spaces dedicated to the 842-square-mile Stellwagen Bank National Marine Sanctuary, maritime science education, maritime art, and the outdoor Seapocket Aquarium, which features interactive touch tanks.

13. Ravenswood Park

For a serene retreat, visitors can escape to this 600-acre wooded area, managed by the Trustees of Reservations.

Ravenswood Park comprises a collection of woodlots that were acquired by shipowner and merchant Samuel Sawyer (1815-1899), who bequeathed the land to the town for conversion into a park after his passing.

The reservation features more than ten miles of broad, predominantly level carriage paths, with varied topography providing expansive views of Gloucester Harbor.

The landscape is dotted with substantial granite boulders, while low-lying areas contain swamps and vernal pools.

14. Cultural Center at Rocky Neck

The Rocky Neck Art Colony (RNAC) continues to flourish and is housed within an evocative Carpenter Gothic meetinghouse constructed in 1877.

Purchased by the colony in 2012, this venue features two levels of galleries showcasing exhibitions curated by the RNAC’s Cultural Center Exhibitions Committee.

Regularly, there is a full calendar of themed and solo exhibitions lasting approximately five weeks, culminating in an annual juried show for RNAC members at year’s end.

This unique building also serves as a venue for talks, workshops, concerts, and a range of other events.

15. Fishermen’s Wives Memorial

For centuries, the fishing community in Gloucester was supported by the resilient women who remained on the shore, tirelessly ensuring the continuity of life.

In recognition of their contributions, the Gloucester Fishermen’s Wives Association (GFWA) established this poignant memorial, contrasting the more renowned Man At the Wheel, depicting a woman gazing towards the harbor entrance, with a boy by her side and an infant in her left arm.

This monument, dedicated in 2001, is located at the northern end of Stage Fort Park at 107 Western Ave.