Rachel’s Guide to Gloucester
Food scene
Short & Main
36 Main StA little pricey but amazing atmosphere and best pizza in town!
Beachy patio area, amazing smoothies, vintage clothing - good vibes all around!
Castaways Vintage Cafe
65 Main StBeachy patio area, amazing smoothies, vintage clothing - good vibes all around!
Seasonal restaurant conveniently located on the water with a unique Mediterranean menu
10 locals recommend
Yella on the Water
25 Western AveSeasonal restaurant conveniently located on the water with a unique Mediterranean menu
Markouk Bread
338 Main StGreat Lebanese for quick takeout order for your beach day or night in!
Sugar Magnolias
112 Main StDon't miss this unique breakfast menu!
Breakwater Poke Company
7 Pleasant StreetNew Poke place for another fast but quality dining option!
My personal favorite seasonal restaurant. Located on the charming rocky neck area of Gloucester. Beautiful deck, amazing seafood!
28 locals recommend
The Studio
51 Rocky Neck AveMy personal favorite seasonal restaurant. Located on the charming rocky neck area of Gloucester. Beautiful deck, amazing seafood!
Do not miss this hole in the wall spot. The most delicious ice cream spot on the north shore. Ice cream sandwiches, ice cream stuffed cannolis, the most unique flavors you could think of!
10 locals recommend
Holy Cow Ice Cream Cafe
80 Pleasant StDo not miss this hole in the wall spot. The most delicious ice cream spot on the north shore. Ice cream sandwiches, ice cream stuffed cannolis, the most unique flavors you could think of!
Do not miss this authentic Italian bakery in Gloucester's West End! Perfect beach sandwiches on a homemade roll. Worth the wait!
36 locals recommend
Virgilio's Italian Bakery
29 Main StDo not miss this authentic Italian bakery in Gloucester's West End! Perfect beach sandwiches on a homemade roll. Worth the wait!
Causeway Restaurant
78 Essex AveGreat fresh local seafood and impressive portions!
Tonno Restaurant
2 Main StGreat spot for fresh seafood right on Gloucester's main street!
Not technically Gloucester but Rockport is a must stop destination while on Cape Ann and this is THE spot to grab dinner while you're there!
46 locals recommend
Feather & Wedge
5 Main StNot technically Gloucester but Rockport is a must stop destination while on Cape Ann and this is THE spot to grab dinner while you're there!
Oak to Ember
The newest and coolest restaurant in Gloucester! Great farm to table option.
Tacos Lupita
1802 65th StCheap, authentic, and delicious Mexican food. Need I say more??
I can’t say enough about this little gem on Rocky Neck. My favorite food spot in the area! Amazing menu/chef, stunning views. Portions are on the smaller side so get an app, dessert, and spend your slow evening in this beautiful place!
12 locals recommend
Rudder Restaurant
73 Rocky Neck AveI can’t say enough about this little gem on Rocky Neck. My favorite food spot in the area! Amazing menu/chef, stunning views. Portions are on the smaller side so get an app, dessert, and spend your slow evening in this beautiful place!
Absolutely nothing like it. Worth the drive over to the only restaurant in quant Annisquam for this small but high quality menu. Make a reservation ahead of time it can book up. Only open seasonally.
10 locals recommend
Talise
33 River RdAbsolutely nothing like it. Worth the drive over to the only restaurant in quant Annisquam for this small but high quality menu. Make a reservation ahead of time it can book up. Only open seasonally.
Salted Cod Arthouse
Unique wine bar perfect for grabbing a drink or coffee and exploring Rocky Neck
Sightseeing
Cape Ann Museum
27 Pleasant StGreat rainy day activity!
Eastern Point Lighthouse
Beautiful drive and scene!
Great 360 views of the water, playground for kids, a cute beach (Half Moon), and various events like the weekly farmer's market.
45 locals recommend
Stage Fort Park and Beach
24 Hough AveGreat 360 views of the water, playground for kids, a cute beach (Half Moon), and various events like the weekly farmer's market.
Great option to mix it up when you've been at Good Harbor for days!
66 locals recommend
Wingaersheek Beach
Great option to mix it up when you've been at Good Harbor for days!
Another great rainy day spot! Interesting history and beautiful location right on the water.
55 locals recommend
Hammond Castle Museum
80 Hesperus AvenueAnother great rainy day spot! Interesting history and beautiful location right on the water.
Well known for its quarries and stunning views. An easy walk/hike for anyone!
115 locals recommend
Halibut Point State Park
Gott AvenueWell known for its quarries and stunning views. An easy walk/hike for anyone!
Whale watching
27 Rogers StA favorite for tourists visiting Gloucester!
Nothing like a good massage to make you feel like you're truly on vacation! Don't miss this gem right downtown.
Saltwater Massage Studio
65 Pleasant StNothing like a good massage to make you feel like you're truly on vacation! Don't miss this gem right downtown.