Guidebook for Gloucester
Food Scene
Closest grab and go restaurant to the house (15 min walk, 3 min drive). BE WARNED: the slices are daunting can easily feed two people. Add an aranchini (rice ball) to your meal as well, you won't be disappointed.
Captain Hooks
406 Washington StClosest grab and go restaurant to the house (15 min walk, 3 min drive). BE WARNED: the slices are daunting can easily feed two people. Add an aranchini (rice ball) to your meal as well, you won't be disappointed.
This is the best local place to stock up on lunch items for the day. Subs are substantial and delicious.
Destino's
129 Prospect StThis is the best local place to stock up on lunch items for the day. Subs are substantial and delicious.
This is the quick local breakfast spot for sandwiches, baked goods, and coffee. You will never want to go to Dunks again.
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Jim's Bagel & Bake Shoppe
34 Railroad AveThis is the quick local breakfast spot for sandwiches, baked goods, and coffee. You will never want to go to Dunks again.
This is our go to for nice sit down dinners - sushi, seafood, and other American eats.
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Minglewood Harborside
25 Rogers StThis is our go to for nice sit down dinners - sushi, seafood, and other American eats.
Charlie's Place
83 Bass AveDo not go anywhere else in town for Lobster Rolls.
The most Gloucester-esque restaurant you can imagine with plenty of seafood offerings and marshland views.
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Lobsta Land Restaurant
84 Causeway St The most Gloucester-esque restaurant you can imagine with plenty of seafood offerings and marshland views.
Best place in town for a sit down breakfast. Do not order more than one pancake.
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George's Coffee Shop
178 Washington StBest place in town for a sit down breakfast. Do not order more than one pancake.
Arts & Culture
This is the oldest Art Colony in the United states, featuring local artist galleries and sit-down restaurants.
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The Cultural Center at Rocky Neck
6 Wonson StThis is the oldest Art Colony in the United states, featuring local artist galleries and sit-down restaurants.
Shopping
This is the most scenic/popular shopping area on the island. The entire street is scattered with stores and places to eat. Parking can be tricky on weekends.
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Bearskin Neck
Bearskin Neck This is the most scenic/popular shopping area on the island. The entire street is scattered with stores and places to eat. Parking can be tricky on weekends.
Tons of restaurants as well as mom and pop shops to buy souvenirs.
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Main Street
Main StreetTons of restaurants as well as mom and pop shops to buy souvenirs.
Sightseeing
This is the most breathtaking road in Gloucester which most often miss. Beautiful coastline with waves crashing on the rocks.
Atlantic Road
Atlantic RoadThis is the most breathtaking road in Gloucester which most often miss. Beautiful coastline with waves crashing on the rocks.
Free parking where you can walk along the breakwater and get the best views of the harbor.
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Eastern Point Lighthouse
Free parking where you can walk along the breakwater and get the best views of the harbor.
This road has great views of Gloucester harbor and is where you will find the famous Fisherman's Memorial Statue.
Stacy Boulevard
Stacy BoulevardThis road has great views of Gloucester harbor and is where you will find the famous Fisherman's Memorial Statue.
Parks & Nature
This park has $5 parking, rock trails, and awesome views of the Atlantic Ocean.
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Parco Statale di Halibut Point
Gott AvenueThis park has $5 parking, rock trails, and awesome views of the Atlantic Ocean.
Most popular beach on the island. Get here before 9:30am to guarantee parking or take a cab. $25 per car.
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Spiaggia di Good Harbor
Most popular beach on the island. Get here before 9:30am to guarantee parking or take a cab. $25 per car.
Perfect beach for little kids since the beach has no drop off and there are rocks to explore/play on. You can kayak here or pay for parking.
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Spiaggia di Wingaersheek
Perfect beach for little kids since the beach has no drop off and there are rocks to explore/play on. You can kayak here or pay for parking.
Dogtown
There are plenty of flat, tree-lined trails to go hiking on.
Island with twin light houses you can climb to the top of. Shuttles leave daily out of Rockport Harbor.
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Thacher Island
Island with twin light houses you can climb to the top of. Shuttles leave daily out of Rockport Harbor.
Drinks & Nightlife
This bar has is situated on an outdoor deck with live music and a rum shack. People of all ages attend and is always lively on a Friday or Saturday, day or night, leading to its nickname "the black hole."
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Mile Marker One Restaurant
75 Essex Ave This bar has is situated on an outdoor deck with live music and a rum shack. People of all ages attend and is always lively on a Friday or Saturday, day or night, leading to its nickname "the black hole."
Essentials
Market Basket
400 Somerville Ave All encompassing grocery store with good prices.
Buy all your alcohol related goods here or else pay full price!
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Liquor Locker
287 Main StBuy all your alcohol related goods here or else pay full price!