City Guides: Things to do While Boating in Gloucester, Massachusetts
Sitting along Cape Ann’s rocky shores, northeast of Salem and near Rockport, Gloucester is one of America’s oldest seaports. Maritime history, art and coastal charm come beautifully together. From its working harbor and pristine beaches to art galleries, waterfront dining and whale-watching excursions, Gloucester offers the perfect mix of tradition and adventure. Whether you arrive by car or by private boat slip rental, this Bay State city will reel you in with its authentic New England spirit.
Gloucester Harbor and the Fishermen’s Memorial
The heart of the city beats at Gloucester Harbor, where fishing boats, schooners and yachts glide past centuries of history. Stroll along the Stacy Boulevard Esplanade to visit the Fishermen’s Memorial, known locally as The Man at the Wheel. This bronze statue honors generations of Gloucester fishermen who have braved the Atlantic. It’s one of the most photographed spots in town. Nearby, plaques list the names of those lost at sea, a poignant reminder of the city’s maritime roots.
Good Harbor Beach
When summer rolls in, locals and visitors flock to Good Harbor Beach. This stunning stretch of white sand is perfect for swimming, sunbathing and tide pooling. At low tide, you can even walk across the sandbar to Salt Island, a small rocky outcrop with panoramic views of the coastline. The surf is gentle enough for families but lively enough for boogie boarders. The sunsets are pure magic.
Hammond Castle Museum
Overlooking the Atlantic on the rocky cliffs of Magnolia, Hammond Castle Museum feels like something out of a European fairytale. Built in the 1920s by inventor John Hays Hammond Jr., this medieval-style castle houses fascinating artifacts, a Roman-style courtyard and exhibits celebrating Hammond’s scientific contributions. The sweeping ocean views from the castle’s terrace are worth the trip from private boat lifts for rent.
Rocky Neck Art Colony
Gloucester has long been a haven for artists, and Rocky Neck Art Colony is its creative heart. One of the oldest continuously operating art colonies in the U.S., this charming waterfront neighborhood is lined with galleries, studios and cafes. Browse paintings inspired by the sea, meet local artists and stay for lunch overlooking Smith Cove and its array of fishing boats and sailboats.
Maritime Gloucester
At Maritime Gloucester, visitors can dive into the region’s nautical heritage through hands-on exhibits, an aquarium and historic vessels. Located right on the working waterfront, it’s both a museum and a living reminder of Gloucester’s role as America’s oldest seaport. Don’t miss the chance to board the Schooner Ardelle, a locally built wooden schooner offering scenic harbor sails.
Whale Watching Adventures
Gloucester is one of the best whale-watching destinations in New England. It has easy access to Stellwagen Bank and Jeffrey’s Ledge — two feeding grounds filled with humpbacks, finbacks and minke whales. Local operators like Cape Ann Whale Watch and 7 Seas Whale Watch offer unforgettable excursions where sightings are almost guaranteed. The thrill of seeing a whale breach against the Atlantic backdrop is something you’ll never forget.
Stage Fort Park
For history and relaxation combined, visit Stage Fort Park, the site of Gloucester’s founding in 1623. Today, it’s a beautiful public space with walking trails, picnic areas and small beaches like the cozy cove of Half Moon Beach. It’s an ideal spot for a laid-back afternoon of ocean breezes and harbor views from a private boat dock for rent.
Are you looking for a spot to store your yacht, sailboat or trawler? Check out boat docks in New England or boat slips near me to find a home away from home for your boat.
