Sightseeing
Cape Ann is the Whale Watching Capital of the East Coast and you will soon find out why ... from the boat trip to the crew, and the magnificent experience typically found on a whale watch.
41 locals recommend
Cape Ann Whale Watch
415 Main StCape Ann is the Whale Watching Capital of the East Coast and you will soon find out why ... from the boat trip to the crew, and the magnificent experience typically found on a whale watch.
Eastern Point Lighthouse
Walk the Stone Pier called the Breakwater to the end! enjoy sunrise and sunset from this point.
29 locals recommend
Gloucester Fishermen's Wives Memorial
107 Western Ave Walk the Stone Pier called the Breakwater to the end! enjoy sunrise and sunset from this point.
The Cultural Center at Rocky Neck
6 Wonson StGloucester City Hall
9 Dale AveDrive or bike ride over to this beautiful seaside village of Rockport, Massachusetts, where you can enjoy many shops, artist galleries, special views, the famous Motif #1 and nearby beaches.
31 locals recommend
Bearskin Neck
Bearskin NeckDrive or bike ride over to this beautiful seaside village of Rockport, Massachusetts, where you can enjoy many shops, artist galleries, special views, the famous Motif #1 and nearby beaches.
Boston
Boston is wicked awesome. So much to see and do.
Amazing, and quintessential experience for the tourist or game goer, visit America's favorite ballpark and feel the history of America's favorite passtime! Grab a beer and a Fenway Frank and enjoy the games, the views, in the midst of the lore and legend of Fenway.
815 locals recommend
Fenway Park
4 Jersey StAmazing, and quintessential experience for the tourist or game goer, visit America's favorite ballpark and feel the history of America's favorite passtime! Grab a beer and a Fenway Frank and enjoy the games, the views, in the midst of the lore and legend of Fenway.
One of 14 Presidential Libraries in the USA, this stunning IM Pei building is inspiring for all ages.
129 locals recommend
John F. Kennedy Presidential Museum & Library
Columbia PointOne of 14 Presidential Libraries in the USA, this stunning IM Pei building is inspiring for all ages.
Newer to Boston's collection of experiences, this modern building and digital experience, the Edward M. Kennedy Institute for the United States Senate is designed to bring the history of the United States Senate alive – using technology to engage and inspire like never before. The Institute features a representation of the United States Senate Chamber, interactive exhibits, and a reproduction of Senator Kennedy’s office. To experience the Senate Chamber, Chamber Surround, temporary exhibits and Senator Kennedy’s office, please plan for a 1.5 to 2 hour visit.
Edward M. Kennedy Institute for the United States Senate
210 Morrissey BlvdNewer to Boston's collection of experiences, this modern building and digital experience, the Edward M. Kennedy Institute for the United States Senate is designed to bring the history of the United States Senate alive – using technology to engage and inspire like never before. The Institute features a representation of the United States Senate Chamber, interactive exhibits, and a reproduction of Senator Kennedy’s office. To experience the Senate Chamber, Chamber Surround, temporary exhibits and Senator Kennedy’s office, please plan for a 1.5 to 2 hour visit.
Arts & Culture
Cape Ann Museum
27 Pleasant StGloucester Stage Company
267 E Main StRockport Music-Shalin Liu Performance Center
37 Main Stgreat for all ages! take a look inside Gloucester's heritage with a focus on maritime history and happenings.
17 locals recommend
Maritime Gloucester
23 Harbor Loopgreat for all ages! take a look inside Gloucester's heritage with a focus on maritime history and happenings.
Shopping
Main Street
Main StreetLiquor Locker
287 Main StAll you need options in wine, beer and spirits.
gourmet foods meets a world of wine; also offers an innovative tasting experience.
7 locals recommend
Savour Wine & Cheese
76 Prospect Stgourmet foods meets a world of wine; also offers an innovative tasting experience.
The Cave
44 Main StEccentric shop and world of cheese, wines, crackers, and bites!
Common Crow Natural Market
200 Eastern AveAmazing organic market ahead of its time
Market Street
Market StreetEverything from Whole Foods to outlet shopping!
Northshore Mall
210 Andover StLiberty Tree Mall station
Eastern Avenue & Barn Lane station
Gloucester Crossing Road
Gloucester Crossing RoadMarket Basket
400 Somerville AveMarshalls
211 Gloucester Crossing RdThree Lantern Marine and Fishing
7 Parker StFood Scene
Rudder Restaurant
73 Rocky Neck AveBlue Collar Lobster Co at The Gloucester House Restaurant
63 Rogers StSugar Magnolias
112 Main StGreat breakfast and lunch
Walk to breakfast May - October --- amazing menu and offerings with a great view!
Atlantis Oceanfront Inn Hotel In Gloucester, MA
125 Atlantic RdWalk to breakfast May - October --- amazing menu and offerings with a great view!
Favorite coffee shop with eat in tables, and wireless + a lot of locals hanging around!
7 locals recommend
Cape Ann Coffees
86 Bass AveFavorite coffee shop with eat in tables, and wireless + a lot of locals hanging around!
Halibut Point
289 E Main StGreat grub and grilled items. Love chowder ~ ask for the 1/2 and 1/2 for a real treat!
Fun local spot run by a local couple with great food and atmosphere.
8 locals recommend
Stones Pub & Eatery
242 Main StFun local spot run by a local couple with great food and atmosphere.
Katrina's
14 Rogers StValue for $ ... and great nightlife after main dinner period.
timeless menu, with the most wonderful popovers, great selection of beer!
23 locals recommend
Passports
110 Main Sttimeless menu, with the most wonderful popovers, great selection of beer!
If your hungry, you won't be ... true to advertising in every plate!
19 locals recommend
George's Coffee Shop
178 Washington StIf your hungry, you won't be ... true to advertising in every plate!
Potentially one of the best restaurants in the world, if you can get in, take the reservation and enjoy this charming, boutique dining and culinary experience.
34 locals recommend
Duckworth's Bistrot
197 E Main StPotentially one of the best restaurants in the world, if you can get in, take the reservation and enjoy this charming, boutique dining and culinary experience.
Drinks & Nightlife
Cape Ann Brewing Company & Brewpub
11 Rogers StBeauport Hotel Gloucester
55 Commercial StDrift
3 Main StThe Rhumb Line Bar & Restaurant
40 Railroad AveMinglewood Tavern
25 Rogers StPratty's CAV
10 Parker StBeauport Hotel Gloucester
55 Commercial StThe Rhumb Line Bar & Restaurant
40 Railroad AveEntertainment & Activities
Not to be missed! Great family business - The Ellis and Captain Tom will surely show you a great time aboard this magnificent schooner, homebuilt in Essex County, and sailing the Gloucester waters for 15+ years!
15 locals recommend
Schooner Thomas E. Lannon
63 Rogers StNot to be missed! Great family business - The Ellis and Captain Tom will surely show you a great time aboard this magnificent schooner, homebuilt in Essex County, and sailing the Gloucester waters for 15+ years!
The Cape Ann Cinema and Stage
37 Rogers StParks & Nature
absolutely stunning scenery within the park and out to sea!
115 locals recommend
Halibut Point State Park
Gott Avenueabsolutely stunning scenery within the park and out to sea!
Experience a bit of history in Gloucester, overlooking the harbor. Peer down the barrels of the cannons from the American Revolution, or scale the rustic boulders, sit on Pavilion Beach or walk the trails.
45 locals recommend
Stage Fort Park and Beach
24 Hough AveExperience a bit of history in Gloucester, overlooking the harbor. Peer down the barrels of the cannons from the American Revolution, or scale the rustic boulders, sit on Pavilion Beach or walk the trails.
Niles Beach station
Great sunsets, lovely smaller beach
Wingaersheek Beach
Special beach with miles of sea and sand
best beach in the world, with a creek, a swim and walk to island, fantastic shoreline and frequent surfing conditions
118 locals recommend
Good Harbor Beach
best beach in the world, with a creek, a swim and walk to island, fantastic shoreline and frequent surfing conditions
Ravenswood Park offers 600 acres for solitude and quiet contemplation of nature. Whether you prefer to surround yourself with snow-covered hemlocks, experience spring emerging in a burst of color and aroma, or escape the summer’s heat – you’ll find a refuge here. With 10 miles of carriage paths and trails that meander through the park, you can find plenty of room to picnic, bird watch, walk, cross-country ski, and simply appreciate the outdoors. Children love the Ledge Hill Trail – a 2-mile round-trip walk among magical-looking, fern-covered boulders.
26 locals recommend
Ravenswood Park
Ravenswood ParkRavenswood Park offers 600 acres for solitude and quiet contemplation of nature. Whether you prefer to surround yourself with snow-covered hemlocks, experience spring emerging in a burst of color and aroma, or escape the summer’s heat – you’ll find a refuge here. With 10 miles of carriage paths and trails that meander through the park, you can find plenty of room to picnic, bird watch, walk, cross-country ski, and simply appreciate the outdoors. Children love the Ledge Hill Trail – a 2-mile round-trip walk among magical-looking, fern-covered boulders.
Six miles of footpaths, bridle paths, and farm roads (easy walking and great for jogging strollers), some of which are part of the Bay Circuit Trail, crisscross the farm. Rolling grasslands, grazing livestock, stone walls, and historic farm buildings are part of this 1,000 acre pastoral landscape – a rare glimpse into New England’s agricultural past. A gift of Colonel Francis R. Appleton, Appleton Farms is one of the oldest continuously operating farms in the country.
22 locals recommend
Appleton Farms
Massachusetts 1ASix miles of footpaths, bridle paths, and farm roads (easy walking and great for jogging strollers), some of which are part of the Bay Circuit Trail, crisscross the farm. Rolling grasslands, grazing livestock, stone walls, and historic farm buildings are part of this 1,000 acre pastoral landscape – a rare glimpse into New England’s agricultural past. A gift of Colonel Francis R. Appleton, Appleton Farms is one of the oldest continuously operating farms in the country.