Overview
Gloucester is a city in Massachusetts. One of the country's oldest settlements, established in 1623, it serves as America's oldest seaport. Although the sea is contributing less to the city's economy, Gloucester is still a true New England fishing center as immortalized in the movie The Perfect Storm. Rocky Neck, the longest continually operating art colony in North America, is also in Gloucester.
4 things to do · 12 places to eat · 13 places to stay
Updated from Wikivoyage on 1 October 2026 · Something wrong or missing? Improve it on Wikivoyage
Best things about Gloucester
Hammond Castle
Castle overlooking the Atlantic Ocean since 1929, now a museum open to the public, once served as John Hayes Hammond, Jr's laboratory and home, inventor and pioneer of remote control. Hammond held over 400 patents and bu…
Wingaersheek Beach
Cape Ann Whale Watch
Offering guaranteed whale sightings on all tours. Departing twice daily for over 35 years, Cape Ann Whale Watch sails aboard "The Hurricane II", made famous in the 1991 movie The Perfect Storm.
Coastal Fishing Charters
In business since the 1980s offering bluefin tuna fishing charters aboard a classic 35-ft (11-m) boat. Featured in reality TV series Wicked Tuna.
Plan your trip
Best time to visit & weather
Most comfortable: May–Sep. Summer highs reach about 80°F; winter lows dip to about 18°F. Cold months (Jan, Feb) can bring snow and ice; check road conditions. Wettest: Oct and Dec. (climate data from nearby Beverly)
Blue bars: average daily high and low (°F). Purple columns: average monthly rain and melted snow (inches).
Getting there
- From you: to see whether to drive or fly, and how long it takes.
- BOS Boston Logan International Airport, Boston — 25 mi away (major hub). Directions
- PSM Portsmouth International Airport at Pease, Portsmouth — 33 mi away. Directions
From Boston take I-93 or Route 1 to Route 128. It's about 35 mi (56 km).
Full “Get in” guide ↓Budget & where to stay
No prices are listed for this place yet. See the Sleep guide ↓ for options.
Sample 1-day itinerary
Day 1
- Morning Hammond Castle, Wingaersheek Beach
- Lunch Sugar Magnolias
- Afternoon Cape Ann Whale Watch, Coastal Fishing Charters
- Dinner Charlie's Place
Stops are grouped by area so each day needs little backtracking. Check opening hours before you go.
Food for you
Cuisine (tap to filter)
What to ask about, for your diet
Diet labels come from each listing's description and cuisine; “likely” means the cuisine usually has good choices, not a promise. Check with the restaurant. Open the food finder
Photos
Map
Every listing with a location. Tap a pin for its Google Maps link.
Understand
With a population of about 30,000 people, this is the only real city you'll find on Cape Ann.
Gloucester is America's oldest seaport. Established in 1623, the city's roots are tied to the sea. Even with the decline of fishing due to heavy federal regulations, the city has an active waterfront. It also hosts great museums and sites. The Cape Ann Museum has the largest collection of Fitz Henry Lane paintings in the country, Hammond Castle, built by John Hayes Hammond, the father of remote control, Beauport, built by Henry Sleeper and a National Historic Landmark, the Sargent House, home of Judith Singer Sargent, one of the country's first feminists and the Gloucester Maritime Heritage Center, telling the story of the fishing industry and featuring the oldest continuously working railways in the country. Gloucester's City Hall was built in 1871 and has examples of the finest WPA murals in Massachusetts. Gloucester also features a diverse selection of fine restaurants and a delightful downtown.
Local information
- Gloucester city council website
Get in
By car
From Boston take I-93 or Route 1 to Route 128. It's about 35 mi (56 km).
By train
The MBTA commuter rail runs from North Station in Boston to Gloucester via the Newburyport/Rockport line. The trip takes about an hour and costs $7.25 one-way.
By bus
Cape Ann Transportation Authority, (CATA), phone: +1 978-283-7916, runs buses on Cape Ann including special routes during the summer.
Get around
- Gloucester Visitor Information Center, off Rt. 127 at Stage Fort Park, Phone: +1 978-281-8865. Seasonal. Get a free brochure on the Gloucester Maritime Trail which describes four self-guided walks.
See
- Fisherman's Memorial Statue, Stacy Blvd. Iconic statue of a typical storm-dressed "Old Salt" at the wheel commemorating the over ten thousand Gloucester fishermen who have been lost at sea.
- Rocky Neck Art Colony, Rocky Neck Av. off East Main. The oldest art colony in America, with galleries of local artists, bars and restaurants.
Do
Gloucester was voted "Top 5 whale watching destinations in the World" by the World Wildlife Fund as several species of whales migrate to the shores of Gloucester every year to feed on the abundant natural resources. Whale watching enthusiasts can expect to potentially see humpback whales, northern right whales, minke whales, blue whales, fin whales, sperm whales, pilot whales among other whale species.
Do Hammond Castle
Castle overlooking the Atlantic Ocean since 1929, now a museum open to the public, once served as John Hayes Hammond, Jr's laboratory and home, inventor and pioneer of remote control. Hammond held over 400 patents and built a weather chamber in his home where he tried to control rain, snow, sleet and wind inside his lab.
- Stage Fort Park The site of the city's first establishment, with giant bronze plaque to prove it, the fort retains the original cannons used for defense pointing towards Gloucester Harbor. A good place to enjoy a picnic, have a swim at two of the parks beaches, or wander through the maze of stone step remains of the original fort. Gloucester's Visitor and Welcoming Center is also found here.
Do Wingaersheek Beach
Events
- St. Peter's Fiesta This five-day festival began in 1927 and is organized by the Italian American community in Gloucester. It honors St. Peter, the patron saint of fisherman, and locals come out to pay their respects and pray for the safe return of all fishermen. The Fiesta features all the carnival rides, street performers and food stalls you'd expect from any classic summer festival. The real highlight, however; is the Greasy Pole contest. An idea imported from Sicily, a 45-foot pole is suspended over the ocean, and slathered in all manner of greasy, slippery substances imaginable. A flag is attached to the end, then contestants try to walk across. Whoever grabs the flag first is declared the winner for that day. Winners don't get much, outside of bragging rights and free drinks for the night. Yes, alcohol is involved, injuries occur, and the Coast Guard is on hand for safety. The contest runs daily throughout the festival with Sunday being considered the championship round.
Buy
The main downtown area of Gloucester holds a number of local shops and restaurants for many tastes. Although the downtown area has lost the department stores it used to have, many new shops and eateries have opened. The area is a pleasant walk around, and it's easy to drop in and visit shops for Souvenirs, such as the Weathervane and the House of the Raven. The area is changing daily, into a more tourist friendly venue for visitors attracted to a still operational fishing port. Although the city has suffered from the loss of the fishing industry, residents have moved towards recognizing other avenues that the city can survive economically, including tourism, while still maintaining the active fishing community. The main street area has begun sprouting condos downtown, and a new retail spot has arisen in the former Browns Mall with a kitchen specialty store and a few bookshops and antique stores.
For more typical needs beyond souvenirs and an enjoyable downtown section, there are two main plazas in town, one on Eastern Avenue, and one on Bass Avenue which hold supermarkets and drug stores, along with other outlets.
Eat
Breakfast
Eat Sugar Magnolias
This is one of the most popular places for breakfast in town, fresh, interesting takes on breakfast foods.
Eat Charlie's Place
Serves a nice breakfast, inexpensive.
Eat Two Sisters Coffee Shop
Have some nice Swedish Nisu bread.
Lunch & dinner
Eat Causeway Restaurant
Not fancy, huge portions, lower than average prices.
Eat Destino's Subs & Catering
Some of the best subs in town, grab a cheesesteak.
Eat Sclafani's Bakery
Famous for their Italian subs on fresh baked bread (lunch only).
Eat Maria's
Tasty local sit down pizza place with thin crust pizza.
Eat Sebastian's Pizza
Really great local pizza.
Eat Virgilio's Bakery
Try the St. Joseph sandwich, also a great selection of Italian grocery products.
Splurge
Eat Passports
Extremely popular restaurant located downtown.
Eat Duckworth's Bistrot
Upscale restaurant located in East Gloucester.
Eat Franklin Cape Ann
Gloucester branch of a Boston restaurant, great bar for cocktails.
Sleep
Stay Lanes Cove House Bed & Breakfast and Vacation Homes
A beautiful restored 1800s Victorian, with 3 lovely guest rooms. a roomy upscale vacation home for families, and a trendy small apartment for a couple.
Hotels and motels
Stay Colonial Inn
Stay Good Harbor Beach Inn
Stay Sea Lion Motel
Stay Wingaersheek Motel
Campground
Go next
A trip to Rockport makes a nice day.
Nearby
Rockport
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Ipswich
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Beverly
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Marblehead
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Salem
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My experience
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