Add to that the freshly caught lobsters and authentic coastal ambiance, and there’s no denying that Gloucester is one of the best coastal towns in New England. It has almost everything necessary to create the perfect coastal getaway, with one exception (which luckily, is just a few miles away).
Where Is Gloucester, MA and Why Visit?
Eastern Point Lighthouse in Gloucester, MA remains a tourist favorite.In an area so culturally aligned with the ocean, it’s no surprise that sustainable travel ideas in Gloucester are around every corner—from bait-to-plate seafood to car-free access to the area’s many activities.
How to Get to Gloucester, MA
By highway, coastal roads, or train, Gloucester is a quick trip from Boston.Or ditch the car altogether by taking the commuter rail from Boston. Gloucester is the 11th stop from North Station on the Newburyport/Rockport line, and the Cape Ann Transportation Authority offers $3 day passes for the many Cape Ann bus routes. As an alternative, enjoy Gloucester’s idyllic water shuttle service or rent a set of wheels from Gloucester E-Bike for the ultimate sustainable Gloucester getaway.
Related: The Most Charming Towns in New England to Visit This Summer, According to Travel Expert Samantha Brown
Locals recommend making Good Harbor Beach parking reservations well in advance.Parking in Gloucester, MA
Related: This Is the Most Underrated Beach Town in America—And It’s Affordable Too
Maritime Gloucester hosts the popular Annual Gloucester Schooner Festival each summer.17 Unique Things to Do in Gloucester, MA
1. 7 Seas Whale Watch
Allow half a day in Gloucester to go on 7 Seas Whale watching adventure.As one of the most beloved beaches along the New England coastline, Good Harbor Beach is a not-to-be-missed addition to any Gloucester, MA weekend getaway. Its gentle waves and silky-smooth sand make for the perfect coastal beach day, but low tide also offers the opportunity to walk across a sandbar to visit Salt Island.
3. Maritime Gloucester
A seaside castle—what could be better? Hammond Castle Museum, an old-world European-style castle built by John Hays Hammond Jr. starting in 1924, took four years to construct, and its unique architecture, indoor pools, and medieval artifacts are as Instagram-worthy as they are fascinating. It's one of the coolest castles in the U.S., and a must-see attraction in Gloucester.
5. Gloucester Fisherman’s Memorial
Gloucester Fisherman’s Memorial was sculpted by Leonard Craske in 1925 to honor Gloucester's 300th anniversaryAn abandoned 17th-century settlement, Dogtown—once known as Commons Settlement—is a popular hiking spot, in part due to its beguiling history and inspirational word-boulders. Visitors are welcome to explore, but local organizations also offer occasional walking tours that provide historical background and answer the popular question: Is Gloucester’s Dogtown a ghost town?
7. Local Seafood Shacks and Sustainable Dining
Local nonprofit Gloucester Fresh is a one-stop resource for seafood sustainability information. It also showcases markets and restaurants that serve fish from Gloucester’s boats—like lobster in the rough favorite Blue Collar Lobster.
8. Gloucester’s Famous Greasy Pole Contest
Gloucester's Greasy Pole contest is reason enough to plan a Gloucester getaway.Locals and visitors alike flock to Gloucester’s many farmers’ markets and locally minded grocers like Common Crow Natural Market. Cedar Rock Gardens, Marshall’s Farmstand, and Annisquam Farmers Market all have their unique offerings, plus Backyard Growers hosts an annual festival featuring farm-fresh goodies, libations, and the best of Gloucester’s foodie scene.
10. Meet Gloucester’s Hardworking Fishermen
Captain Mike Frontiero, owner and captain of the Dunlin lobster boat, is one of Gloucester's fishermen.Depending on the year, as few as 35 Gloucester-based boats can haul in over 4 million pounds of cod, haddock, flounder, and other groundfish, according to Gloucester Fresh. Most of the fishermen live in and around Gloucester, and frequent local watering holes, fish markets, and restaurants—or even own them. So, the chances of meeting them when out and about are good—even Captains Dave Marciano, T. J. Ott, and Dave Carraro—stars of the 2021 season of the National Geographic show Wicked Tuna.Ask about a day in the life of a fisherman or debate the idea of “Maine lobster,” about which Mark Ring, Captain of the Stanley Thomas, says, “There’s always been the misconception about Maine lobster, but […] it’s the same lobster from Jersey to Labrador. So, Maine can call it a Maine lobster, but [Gloucester] lobster is the same…only, we think it’s better.”
11. Sailing the Harbor and Beyond
The Cape Ann area offers visitors opportunities for sailing, chartered fishing, kayaking, and more.Lighthouses, lobstering, and the ceremonial scattering of ashes in Gloucester are all theme options for the tours offered by Cape Ann Harbor Tours. The organization also offers the popular water shuttle, providing transport to many of the area’s popular sights and hotels, including the Rocky Neck Art Colony, Gloucester’s West End, Solomon Jacobs Park, and more.
13. Shopping on Main Street, Gloucester
Gloucester’s shopping scene offers quaint streets with oodles of boutiques—from coastal New England chic to the eclectic finds at The Brass Monkey. Globally inspired musical instruments, clothing, and handbags are always in stock at Floating Lotus, and pets reign supreme at Happy Tails Shoppe. Leave time for Pop Gallery, where the owner gives vintage clothing a new life with screen-printed coastal motifs.
14. Coastal Thrifting and Antiques
Spend the day shopping for coastally inspired gifts, antiques, and vintage finds.The Rocky Neck Art Colony is one of the oldest continually operated artist colonies in the United States and is home to dozens of artists, galleries, and art experiences. In terms of festivals, autumn’s Cape Ann Plein Air attracts artists from around the country. But if you’re looking for a hands-on art experience in Gloucester, MA, Calvo Wood Carving School offers many workshops.
16. What is Motif No. 1?
Motif No. 1, in Gloucester, MA, is as popular with artists as it is with visitors.Admittedly, it’s an odd name for a tourist attraction, but Gloucester’s Motif No. 1 is the most painted building in the world. This small red shack was initially built in the 1840s, and artists, including the famed marine artist Fitz Henry Lane, have long been attracted to its authentic seaside charm. It has since been reconstructed, but its coastal allure endures.
17. Visit Gloucester’s Film-Famous Bar
The Perfect Storm, starring George Clooney and Mark Wahlberg, tells the tragic story of Gloucester's swordfishing boat, the Andrea Gail.Though the film The Perfect Storm premiered in 2000, people still visit its famous bar, the Crow’s Nest, to see for themselves where the likes of Mark Wahlberg and George Clooney filmed scenes. The movie tells the story of the Gloucester fishing boat, the Andrea Gail, that was lost at sea after being caught in a historic storm.
Where to Eat in Gloucester, MA
Cape Ann restaurant,The Gloucester House, helped put fried calamari on the map.Related: 11 Can’t-Miss Things to Do on Cape Cod, According to a Local Travel Expert
Visitors looking to prioritize time along the working harbor can stay at Harborview Inn, a bed & breakfast with sweeping harbor views, or Beauport Hotel Gloucester—both are also close to the train station. It’s also worth exploring rentals in the heart of the Rocky Neck Art Colony, many of which are owned by local artists.
The One Thing You Couldn’t Ignore
The The Shalin Liu Performance Center at Rockport Music offers sweeping views of the ocean.Related: 11 Can’t-Miss Things to Do on Cape Cod, According to a Local Travel Expert
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