Shelter Island guidebook

Lily
Shelter Island guidebook

Food scene

Great Mexican take out (or sit outside in the backyard), smoothies, etc. A short walk from the rental.
16 locals recommend
Maria's Kitchen
55 N Ferry Rd
16 locals recommend
Great 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.
34 locals recommend
SALT Waterfront Bar & Grill
63 S Menantic Rd
34 locals recommend
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.
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.
61 locals recommend
Vine Street Café
41 S Ferry Rd
61 locals recommend
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.
Italian fare in the Heights
10 locals recommend
Isola
15 Grand Ave
10 locals recommend
Italian fare in the Heights
Go for a cocktail and watch the sunset!
19 locals recommend
Ram's Head Inn
108 S Ram Island Dr
19 locals recommend
Go 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 Road
Sit outside with a bottle of Rose. Don't miss live music & King Andrew Cheese mobile cheese shop.
Great take out seafood and fried chicken!
22 locals recommend
Commander Cody's Seafood
41 Smith St
22 locals recommend
Great 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.
93 locals recommend
Sunset Beach
Shore Rd
93 locals recommend
Very pricey but if that doesn't scare you, then it's worth it for a sunset cocktail or dinner on Crescent beach.
Fantastic take-out or casual dine in pizza!
Slice pizza
3 North Ferry Road
Fantastic take-out or casual dine in pizza!
More affordable diner food option on the Island
10 locals recommend
The Islander
63 N Ferry Rd
10 locals recommend
More affordable diner food option on the Island
Coffee and pastry spot
22 locals recommend
Stars Cafe
17 Grand Ave
22 locals recommend
Coffee and pastry spot
Great ice cream!
8 locals recommend
Tuck Shop
75 N Menantic Rd
8 locals recommend
Great ice cream!
Only grocery store on the island. Open until 8pm.
28 locals recommend
IGA Shelter Island
75 N Ferry Rd
28 locals recommend
Only 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 Avenue
More casual sister restaurant at the Chequit. Good spot for dinner or hang at the bar and watch football.
Sushi/Japanese restaurant in the Chequit Hotel.
Weakfish at The Chequit
23 Grand Avenue
Sushi/Japanese restaurant in the Chequit Hotel.
Great bagels. Try the rosemary and salt!
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.
17 locals recommend
The Pridwin
81 Shore Rd
17 locals recommend
Beautiful remodeled hotel with bar and restaurant. Go for a cocktail, sit on the lawn and watch the sunset.
Upscale bistro. Very good rotisserie chicken.
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.
18 locals recommend
Sylvester Manor Educational Farm
80 N Ferry Rd
18 locals recommend
There 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.
70 locals recommend
Mashomack Preserve
79 S Ferry Rd
70 locals recommend
A must-do/see on the island! Check out the trails - some of which go to the beautiful Manor House.

Activities

Mini golf and ice cream
9 locals recommend
Shelter Island Whale's Tale
3 Ram Island Rd
9 locals recommend
Mini 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)
12 locals recommend
Wades Beach
114 S Midway Rd
12 locals recommend
About 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).
14 locals recommend
Crescent Beach
14 locals recommend
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).
Our favorite beach! Beautiful views. Dog friendly. No lifeguards on duty.
Menhaden Lane Beach
Menhaden Lane
Our favorite beach! Beautiful views. Dog friendly. No lifeguards on duty.
Beautiful and quiet strip of beach.
Shell Beach
Beautiful and quiet strip of beach.