Shelter Island guidebook
Food scene
Great Mexican take out (or sit outside in the backyard), smoothies, etc. A short walk from the rental.
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Maria's Kitchen
55 N Ferry RdGreat Mexican take out (or sit outside in the backyard), smoothies, etc. A short walk from the rental.
Dine outdoors at the Restaurant, or grab a casual drink / bite from the food truck at the Shipwreck bar -- one of our favorite activities on a Thursday or Friday night. Live music most evenings in the Summer.
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SALT Waterfront Bar & Grill
63 S Menantic RdDine outdoors at the Restaurant, or grab a casual drink / bite from the food truck at the Shipwreck bar -- one of our favorite activities on a Thursday or Friday night. Live music most evenings in the Summer.
One of our favorite restaurants on the island for a special occasion. A little pricy but the food is excellent (highly recommend the Calamari Salad!). Reservations recommended.
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Vine Street Café
41 S Ferry RdOne of our favorite restaurants on the island for a special occasion. A little pricy but the food is excellent (highly recommend the Calamari Salad!). Reservations recommended.
Isola
15 Grand AveItalian fare in the Heights
Ram's Head Inn
108 S Ram Island DrGo for a cocktail and watch the sunset!
Sit outside with a bottle of Rose. Don't miss live music & King Andrew Cheese mobile cheese shop.
White Oak Wine Garden
2 Manwaring RoadSit outside with a bottle of Rose. Don't miss live music & King Andrew Cheese mobile cheese shop.
Commander Cody's Seafood
41 Smith StGreat take out seafood and fried chicken!
Very pricey but if that doesn't scare you, then it's worth it for a sunset cocktail or dinner on Crescent beach.
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Sunset Beach
Shore RdVery pricey but if that doesn't scare you, then it's worth it for a sunset cocktail or dinner on Crescent beach.
Slice pizza
3 North Ferry RoadFantastic take-out or casual dine in pizza!
The Islander
63 N Ferry RdMore affordable diner food option on the Island
Stars Cafe
17 Grand AveCoffee and pastry spot
Tuck Shop
75 N Menantic RdGreat ice cream!
IGA Shelter Island
75 N Ferry RdOnly grocery store on the island. Open until 8pm.
More casual sister restaurant at the Chequit. Good spot for dinner or hang at the bar and watch football.
The Tavern at The Chequit
23 Grand AvenueMore casual sister restaurant at the Chequit. Good spot for dinner or hang at the bar and watch football.
Weakfish at The Chequit
23 Grand AvenueSushi/Japanese restaurant in the Chequit Hotel.
The Eccentric Bagel
Great bagels. Try the rosemary and salt!
Beautiful remodeled hotel with bar and restaurant. Go for a cocktail, sit on the lawn and watch the sunset.
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The Pridwin
81 Shore RdBeautiful remodeled hotel with bar and restaurant. Go for a cocktail, sit on the lawn and watch the sunset.
Léon 1909
Upscale bistro. Very good rotisserie chicken.
Sightseeing
There are lovely trails through this historic Farm. There's also a farm stand that sells local produce, eggs, meats, cheeses.
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Sylvester Manor Educational Farm
80 N Ferry RdThere are lovely trails through this historic Farm. There's also a farm stand that sells local produce, eggs, meats, cheeses.
A must-do/see on the island! Check out the trails - some of which go to the beautiful Manor House.
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Mashomack Preserve
79 S Ferry RdA must-do/see on the island! Check out the trails - some of which go to the beautiful Manor House.
Activities
Shelter Island Whale's Tale
3 Ram Island RdMini golf and ice cream
Beaches
About 1.5 miles from the house. Family-friendly beach with lifeguards. Parking permits available via the Town App (see signs at beach)
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Wades Beach
114 S Midway RdAbout 1.5 miles from the house. Family-friendly beach with lifeguards. Parking permits available via the Town App (see signs at beach)
Great for watching the sunset. A family-friendly beach with a lifeguard area and food truck. Parking permits available via the Town App (see signs at the beach).
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Crescent Beach
Great for watching the sunset. A family-friendly beach with a lifeguard area and food truck. Parking permits available via the Town App (see signs at the beach).
Menhaden Lane Beach
Menhaden LaneOur favorite beach! Beautiful views. Dog friendly. No lifeguards on duty.
Shell Beach
Beautiful and quiet strip of beach.