Shelter Island
Beaches
***Beach stickers are strictly enforced Memorial Day - Labor Day***
They can be obtained at Town Hall (38 N Ferry Rd) for weekly or monthly use. Fees are roughly $50/$90 - check website or call 631 749 0400. Beach stickers can only be purchased M-Sa. On Saturday the Town Hall closes around 12:00/1:00.
Beautiful beach near by. Perfect for kids. If you walk along the beach you get out to the peninsula across from our house, great spot to crabbing (or just watching them)
Has restrooms.
12 locals recommend
Wades Beach
114 S Midway RdBeautiful beach near by. Perfect for kids. If you walk along the beach you get out to the peninsula across from our house, great spot to crabbing (or just watching them)
Has restrooms.
This beach is perfect for boat/people watching. It’s a spit of land with water on both sides. The inlet side is super calm and great for kids because you can walk out quite far and the water is only up to your knees.
7 locals recommend
Shell Beach
This beach is perfect for boat/people watching. It’s a spit of land with water on both sides. The inlet side is super calm and great for kids because you can walk out quite far and the water is only up to your knees.
Busiest and the most social beach on the island. One of only two on the island with bathrooms and lifeguard on duty. Great for spending the day or going down to watch the sunset in the evening. Across the street form he beach is the famous sunset Beach Hotel and Restaurant.
14 locals recommend
Crescent Beach
Busiest and the most social beach on the island. One of only two on the island with bathrooms and lifeguard on duty. Great for spending the day or going down to watch the sunset in the evening. Across the street form he beach is the famous sunset Beach Hotel and Restaurant.
Good for walks and the longest stretch of beach. Surprisingly calm and good for swimming. Views of North fork and Orient Lighthouse.
Hay Beach Road
Hay Beach RoadGood for walks and the longest stretch of beach. Surprisingly calm and good for swimming. Views of North fork and Orient Lighthouse.
Food scene
Great food and service. Their tuna tartar tacos is delicious. Steaks are great, deserts super yummy! We recommend getting a reservation on the weekends.
61 locals recommend
Vine Street Café
41 S Ferry RdGreat food and service. Their tuna tartar tacos is delicious. Steaks are great, deserts super yummy! We recommend getting a reservation on the weekends.
Shelter Island Seafood
87 North Ferry RoadGreat place for picking up seafood to grill at home.
Breakfast and coffee with a view! Food to go, perfect for easy meals at home, we usually grab a couple of pizzas to make on the grill at home.
41 locals recommend
Marie Eiffel Market
184 N Ferry RdBreakfast and coffee with a view! Food to go, perfect for easy meals at home, we usually grab a couple of pizzas to make on the grill at home.
The Chequit
23 Grand AveAmazing Sushi
The food is good, relaxing spot by the water, live music throughout the summer
34 locals recommend
SALT Waterfront Bar & Grill
63 S Menantic RdThe food is good, relaxing spot by the water, live music throughout the summer
White Oak Wine Stand (2 Manwaring Rd.) is next to the nursery.
Has a small selection of wine’s produced by a local family. On weekends they have tastings and music. A very sweet spot to relax.
By the wine stand you also have King Andrew Cheese for
a freat selection of cheeses, jams, crackers - everything for your charcuterie board. In the summer he is there daily.
White Oak Farm and Gardens
74 North Ferry RoadWhite Oak Wine Stand (2 Manwaring Rd.) is next to the nursery.
Has a small selection of wine’s produced by a local family. On weekends they have tastings and music. A very sweet spot to relax.
By the wine stand you also have King Andrew Cheese for
a freat selection of cheeses, jams, crackers - everything for your charcuterie board. In the summer he is there daily.
Kyles (27 N. Ferry Rd. / (631) 749-0579)
Quirky bakery and restaurants open around 8am for bakery. Sometimes serves breakfast and lunch.
8 locals recommend
Kyle's
27 N Ferry RdKyles (27 N. Ferry Rd. / (631) 749-0579)
Quirky bakery and restaurants open around 8am for bakery. Sometimes serves breakfast and lunch.
The Eccentric Bagel
25 West Neck RoadFor your morning bagel fix, there's now a bagel shop on the island!
Bright, fresh Mexican food. Take-out and there are a couple tables out back. There is also a brewery next door that will allow you to sit at their outside tables to eat if you are having a beer.
16 locals recommend
Maria's Kitchen
55 N Ferry RdBright, fresh Mexican food. Take-out and there are a couple tables out back. There is also a brewery next door that will allow you to sit at their outside tables to eat if you are having a beer.
Tuck Shop
75 N Menantic RdIce cream and soft serve. Open late.
This is a bit of a dive, but a fun experience. Does mostly take out, but has a few seats. Great fried chicken and fish. They also have a fish market.
22 locals recommend
Commander Cody's Seafood
41 Smith StThis is a bit of a dive, but a fun experience. Does mostly take out, but has a few seats. Great fried chicken and fish. They also have a fish market.
Activities
Hiking
79S. Ferry Rd. / 631-749-1001)
Spans 1/3 of the island. There are 1, 3, 6, and 11 mile circuits to walk on. Just know that there are ticks (make sure to protect yourself). It’s nice to make a little contribution as admission to the preserve. If you take the 6 mile, there is a beach where you can stop for a picnic.
70 locals recommend
Mashomack Preserve
79 S Ferry RdHiking
79S. Ferry Rd. / 631-749-1001)
Spans 1/3 of the island. There are 1, 3, 6, and 11 mile circuits to walk on. Just know that there are ticks (make sure to protect yourself). It’s nice to make a little contribution as admission to the preserve. If you take the 6 mile, there is a beach where you can stop for a picnic.
You can rent bicycles at Piccozzi’s. Biking is a popular activity on the island, but know that the island has many hills, so it’s not always the easiest ride.
Piccozzi's Bicycle Rental and Repair
175 North Ferry RoadYou can rent bicycles at Piccozzi’s. Biking is a popular activity on the island, but know that the island has many hills, so it’s not always the easiest ride.
Work out options on the Island:
Yoga
A few places offer yoga on the Island during the summer. Call for schedules.
- Dering Harbor Inn - 13 Winthrop Rd / (631) 749-0900
- Yoga in the Barn at the Haven’s Barn - 16 South Ferry Road. Visit website for schedule www.heidifokineyoga.com
Pilates
SI Pilates and Barre (8 Grand Ave/631-749-5042)
General Fitness
Dering Harbor Inn (13 Winthrop Rd / (631) 749-0900)
The inn houses a gym where you can pay per time you visit.
Tennis
A great tennis pro named Moussa Drame offers classes and clinics at the Dering Harbor Inn. 13 Winthrop Rd. / (631) 749-0160
Free SI town courts - first comes first serve (36 Duvall Rd.)
Barre
Shelter Island Barre Studio (57 N. Ferry Rd./ 917-620-4155)
78 locals recommend
Shelter Island
Work out options on the Island:
Yoga
A few places offer yoga on the Island during the summer. Call for schedules.
- Dering Harbor Inn - 13 Winthrop Rd / (631) 749-0900
- Yoga in the Barn at the Haven’s Barn - 16 South Ferry Road. Visit website for schedule www.heidifokineyoga.com
Pilates
SI Pilates and Barre (8 Grand Ave/631-749-5042)
General Fitness
Dering Harbor Inn (13 Winthrop Rd / (631) 749-0900)
The inn houses a gym where you can pay per time you visit.
Tennis
A great tennis pro named Moussa Drame offers classes and clinics at the Dering Harbor Inn. 13 Winthrop Rd. / (631) 749-0160
Free SI town courts - first comes first serve (36 Duvall Rd.)
Barre
Shelter Island Barre Studio (57 N. Ferry Rd./ 917-620-4155)
Shelter Island Whale's Tale
3 Ram Island RdMini golf and ice cream
Paddle Bording on the Island
-Learn to SUP SI - Private lessons. has a couple of boards available for lessons. Call Scott 516-428-2742
-Venture Out – Rentals at Sunset Beach - 631- 317-7466
78 locals recommend
Shelter Island
Paddle Bording on the Island
-Learn to SUP SI - Private lessons. has a couple of boards available for lessons. Call Scott 516-428-2742
-Venture Out – Rentals at Sunset Beach - 631- 317-7466
Shopping
Saturday Farmers Market. Open from 9-12. Great stop for local produce and other things.
6 locals recommend
Havens House
16 S Ferry RdSaturday Farmers Market. Open from 9-12. Great stop for local produce and other things.
Best farm stand on Shelter, they have veggies right from the field, but also flowers, bread, organic meat, eggs, baked goods etc. Open most days during the summer (sometimes closed on Tuesdays).
The Farmstand at Sylvester Manor
21 Manwaring RdBest farm stand on Shelter, they have veggies right from the field, but also flowers, bread, organic meat, eggs, baked goods etc. Open most days during the summer (sometimes closed on Tuesdays).
Manikas Liquor Shop
179 N Ferry RdMost comprehensive wine / liquor store on the island
Finley's Fiction
8 Grand AvenueFor your summer reads. Adult and Children’s Books / Gifts / Toys
Jack's Marine
188 North Ferry RoadGreat toy store, summer goods, fishing gear. Only place on the island that sells bait.