Gloucester, Massachusetts, looks and feels like a cozy maritime-themed screensaver because, in some ways, it is. The small New England town sits on the peninsula of Cape Ann, surrounded on three sides by sunlight reflecting off glistening ocean water. Simply put: Gloucester has long been an artist’s dreamscape.
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?
Known as one of New England’s most iconic coastal destinations, Gloucester is the crown jewel of Cape Ann—a rocky 30-mile peninsula 45 minutes north of Boston. It’s America’s oldest seaport, and its deep harbor, capable of hosting larger ships, is at the heart of its maritime history. Travelers still love the authentic ambiance of Gloucester’s working waterfront. Nearby, you’ll find endless things to do in Gloucester, including the area’s famous beaches, whale watching excursions, and renowned art galleries—perfect for couples, families, and solo adventuring.
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
Boston’s proximity to Gloucester inspires easy getaways, especially with a straightforward driving route via I-93 North to I-95 North, with Rt. 128 North as the final leg of the trip. Those looking for a more scenic drive can prioritize Route 127 North, a coastal drive through the idyllic New England towns of Beverly, Manchester-by-the-Sea, and Rockport.
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
Parking in Gloucester, MA
Non-resident parking is managed through the parking apps Flowbird (general parking) and Blinkay, which the town requires for non-resident beach parking at Good Harbor Beach, Wingaersheek Beach, and Stage Fort Park. The upside is that advance reservations are accepted. The downside is that visitors sometimes flag glitches with Flowbird’s app, but the town does a good job of sharing parking news via its social media channels.
Related: This Is the Most Underrated Beach Town in America—And It’s Affordable Too
17 Unique Things to Do in Gloucester, MA
1. 7 Seas Whale Watch
With sea captains dating back four generations, 7 Seas Whale Watch offers daily Gloucester-based whale watch experiences from mid-April through mid-October. Guests often see Humpback, finback, and minke whales, and even dolphins, plus the company’s convenient parking is a noteworthy bonus.
2. Good Harbor Beach
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
Although Gloucester boasts museums including the Cape Ann Museum, Beauport, Sleeper-McCann House, and the Sargent House Museum, Maritime Gloucester remains an itinerary standout due to its hands-on discovery exhibits, rich maritime history, and educational aquarium. Maritime Gloucester also hosts the popular Annual Gloucester Schooner Festival each summer.
4. Hammond Castle Museum
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
Speaking of swoony coastal photo opportunities, the Gloucester Fisherman’s Memorial is as iconic as it gets in New England. Sculpted by artist Leonard Craske in 1925 to honor Gloucester’s 300th anniversary, it pays homage to local fishermen lost at sea, including those further memorialized in the film The Perfect Storm (2000).
6. Dogtown Hiking Trails
An 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
Looking for the best weekend getaways in New England? They almost always include seafood. In Gloucester, buy seafood pulled from the sea just hours or minutes before it hits the shaved ice displays of Gloucester Harbor’s many seafood markets, like Cape Ann Fresh Catch—a community supported fishery.
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
Most folks in the Boston area just refer to it as Gloucester’s Greasy Pole contest, but this famous event is part of the five-day St. Peter’s Fiesta. The tradition involves contestants trying to walk, crawl, or scramble across a 40+ foot-long greasy pole, which stretches out over the water—all in hopes of grabbing the flag at the far end for lifelong bragging rights.
9. Farmer’s Markets and Local Grocers
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
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 Artemis is a 64′ Sundeer Ketch that has sailed the globe and now wows guests in Gloucester via private sailing charters. The boat rental site Boatsetter also offers a variety of for-rent boating and sailing options in the Cape Ann area, from a 25-foot fishing boat to a splurgy Gloucester yacht experience.
12. Cape Ann Harbor Tours
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
Among the Main Street shops, goodlinenes studio is a beacon of eco-friendly, thoughtfully designed products. The shop’s in-house line of linen goods remains a top seller, but owner JoAnne Chirico reminds folks that “one of the most sustainable actions is reuse, and Main Street in Gloucester has many [resale] shops…” She recommends Dogtown Books, Edward Beattie Antiques, and the cool vintage clothing at Bananas.
15. Art in Gloucester, MA
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?
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
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
Though Gloucester has plenty of local institutions like The Causeway (think large portions of seafood caught by the owner’s family) and The Gloucester House, which popularized fried calamari, there are always new restaurants joining the ranks, like harborside hot spot Oak to Ember. Here, the smolder of fire welcomes guests as the live-fire grill and smoker char the local fish and daily specials.
Related: 11 Can’t-Miss Things to Do on Cape Cod, According to a Local Travel Expert
Where to Stay in Gloucester, MA
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
Though these highlights round out a proper Gloucester, MA weekend getaway, there’s one exception you should consider. Rockport Music’s Shalin Liu Performance Center, just a few miles north, is a worthy addition to any Gloucester itinerary. The seaside performance center has a mammoth glass wall, overlooking the ocean, adding incredible drama to its many shows and festivals. And yes! It’s also close to one of the many Cape Ann Transportation Authority bus stops.
Related: 11 Can’t-Miss Things to Do on Cape Cod, According to a Local Travel Expert
