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. With a population of about 30k, this is the only real "city" you'll find on Cape Ann.

Get in

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.

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.

• Cape Ann Whale Watch, 415 Main St, ☏ +1 978 283-5110, toll-free: +1 800 877-5110, whale.watch@verizon.net. 7AM-7PM daily. 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. $48.00. 
• 1 Hammond Castle, 80 Hesperus Ave, ☏ +1 978 283-2080. 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. (updated Jan 2018)
• 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.
• Coastal Fishing Charters, 417 Main St, ☏ +1 508 284-2909, toll-free: +1 800 877-5110. 7AM-7PM daily. 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. 
• 2 Wingaersheek Beach. 24 hours daily. (updated Jun 2022)

Events

• St. Peter's Fiesta: Last weekend in June annually. 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, where the Green Life Natural Living Store, and a kitchen specialty store are new additions to the retail scene. There is a sporting goods store called Palazolas, as well as a few bookshops, and antiques 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.

• House of the Raven (House of Raven), 141 Main St., ☏ +1 978-281-1624. M-F 10:10AM-5:30PM, Sa till 5PM. Custom picture framing on-site. Master framer with 30 years experience. Fine gold, sterling silver jewelry, gifts, cards, and souvenirs. 

Eat

• Latitude 43, 25 Rogers St, ☏ +1 978-281-0223. 11:30 AM- 1 AM. Coastal cuisine with a modern twist. Award-winning sushi in a sunken in sushi pit. 

Breakfast

• Sugar Magnolias, 112 Main Street (downtown), ☏ +1 978 281-5310. This is one of the most popular places for breakfast in town, fresh, interesting takes on breakfast foods. 
• Morning Glory, 25 Western Ave, ☏ +1 978 281-1851. Has an outdoor deck overlooking the harbor on Stacy's Boulevard. 
• Charlie's Place, 83 Bass Avenue, ☏ +1 978 281-5002. Serves a nice breakfast, inexpensive. 
• Two Sisters Coffee Shop, 27 Washington Street, ☏ +1 978 281-3378. Have some nice Swedish Nisu bread. 

Lunch & dinner

• Causeway Restaurant, 78 Essex Avenue, ☏ +1 978 281-5256. Not fancy, huge portions, lower than average prices. 
• Destino's Subs & Catering, 129 Prospect Street, ☏ +1 978 283-3100. Some of the best subs in town, grab a cheesesteak. 
• Sclafani's Bakery, 49 Washington Street, ☏ +1 978 283-6622. Famous for their Italian subs on fresh baked bread (lunch only). 
• Charlie's Place, 83 Bass Avenue, ☏ +1 978 281-5002. Nice place to get an inexpensive casual sit down lunch. 
• Maria's, 35 Pearl Street, ☏ +1 978 283-7373. Tasty local sit down pizza place with thin crust pizza. 
• Sebastian's Pizza, 56 Washington Street, ☏ +1 978 283-4407. Really great local pizza. 
• Virgilio's Bakery, 29 Main Street, ☏ +1 978-283-5295. Try the St. Joseph sandwich, also a great selection of Italian grocery products. 

Splurge

• Madfish Bar & Grille, 77 Rocky Neck Ave, ☏ +1 978 281-4554. On the water in Rocky Neck, Also a great bar w/ live Reggae band on Sunday nights in the summer. 
• Studio Lounge & Deck, 51 Rocky Neck Ave, ☏ +1 978 283-4123. Outdoor Deck, right on the harbor. 
• Passports, 110 Main Street, ☏ +1 978 281-3680. Extremely popular restaurant located downtown. 
• Duckworth's Bistrot, 197 East Main Street, ☏ +1 978 282-4426. Upscale restaurant located in East Gloucester. 
• Franklin Cape Ann, 118 Main Street, ☏ +1 978 283-7888. Gloucester branch of a Boston restaurant, great bar for cocktails. 

Drink

• Latitude 43, 25 Rogers St, ☏ +1 978-281-0223. 11:30AM- 1AM. 
• Cape Ann Brewing Co., 11 Rogers St, ☏ +1 978-282-7399. Su-Th 11AM- 11PM, F-Sa 11AM-midnight. 

Sleep

• Lanes Cove House Bed & Breakfast and Vacation Homes, 6 Andrews St (Rte 95 North, to 128 North, to Grant Circle. Take the 3rd exit to 127 North and follow that for 4.5 miles. Bear left on Andrews St.), ☏ +1 978 282-4647. Check-in: 3PM, check-out: 11AM. 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. $120 per night. 

Hotels and motels

• Atlantis Oceanfront Motor Inn, 125 Atlantic Rd, ☏ +1 978-283-0014, toll-free: +1-800-732-6313, fax: +1 978-281-8994. Nice views, terrace or balcony, pool. $$$. 
• 1 Bass Rocks Ocean Inn, 107 Atlantic Rd, ☏ +1 978-283-7600, toll-free: +1 888-802-7666, info@bassrocksoceaninn.com. Check-in: 3PM, check-out: noon. $$. (updated Jun 2016)
• Blue Shutters Beachside Inn, 1 Nautilus Rd, ☏ +1 978 283-1198. $$. 
• Cape Ann Marina Resort, 75 Essex Av, ☏ +1 978 283-2116. 
• Cape Ann Motor Inn, 33 Rockport Rd, ☏ +1 978 281-2900. 
• Captains Lodge Motel, 237 Eastern Av, ☏ +1 978 281-2420. 
• Colonial Inn, 28 Eastern Point Rd, ☏ +1 978 281-1953. 
• Fairview Inn, 52 Eastern Point Rd, ☏ +1 978 281-1758. 
• Good Harbor Beach Inn, 1 Salt Island Rd, ☏ +1 978 283-1489. 
• Sea Lion Motel, 138 Eastern Av, ☏ +1 978 283-7300. 
• Twin Light Manor, 107 Atlantic Rd, ☏ +1 978 283-7500. 
• Vista Motel, 22 Thatcher Rd, ☏ +1 978 281-3410. Check-in: 2:00 p.m., check-out: 11:00 a.m.. Located on a high knoll overlooking Good Harbor Beach. (updated Feb 2021)
• Wingaersheek Motel, 46 Concord St, ☏ +1 978 281-0100. 

Campground

• Cape Ann Campsite, 80 Atlantic St, ☏ +1 978 283-8683. 230 sites. 

Go next

A trip to Rockport makes a nice day.

Routes through Gloucester

END ← Rockport ←	N  S	→ Manchester → Beverly
END ←	N  S	→ Manchester → Peabody
Georgetown ← Essex ←	W  E	→ END
Beverly ← Manchester ←	SW  NE	→ Rockport → END