Overview
Shelter Island is an island and town in Suffolk County in New York. It is between the two forks on Long Island and in total is 6.5 sq miles and was founded by the Sylvester family.
3 sights · 12 places to eat · 8 places to stay
Updated from Wikivoyage on 1 October 2026 · Something wrong or missing? Improve it on Wikivoyage
Best things about Shelter Island
Mashomack Nature Preserve
There is a nice nature preserve that would be a great place to see. It is part of the Nature Conservancy and comprises 1/3 of the island.
Kissing Rock
Also, there is a huge, well-known rock located at the end of Crescent Beach that was redecorated immediately after 9/11.
The Ram's Head Inn
Was the site of the Shelter Island Conference on the Foundations of Quantum Mechanics in 1947. Many famous physicists attended, including Oppenheimer and Feynman. A small plaque commemorates the event.
Plan your trip
Best time to visit & weather
Most comfortable: May–Oct. Summer highs reach about 83°F; winter lows dip to about 15°F. Cold months (Jan, Feb) can bring snow and ice; check road conditions. Wettest: Oct and Aug. (climate data from nearby Waterbury)
Blue bars: average daily high and low (°F). Purple columns: average monthly rain and melted snow (inches).
Getting there
- From you: to see whether to drive or fly, and how long it takes.
- HVN Tweed New Haven Airport, New Haven — 31 mi away. Directions
- WST Westerly State Airport, Westerly — 34 mi away. Directions
- BDL Bradley International Airport, Hartford — 63 mi away (major hub). Directions
In order to get onto this island, you must take either:
Full “Get in” guide ↓Budget & where to stay
- Places to stay listed here: about $235–$235 a night (typical $435), from 2 listed prices.
- Estimated daily budget per person (room, two meals, local transport and an activity): budget ~$280, mid-range ~$510, comfortable ~$400.
Options are grouped as Hotels, Bed and breakfasts in the Sleep guide ↓.
Sample 1-day itinerary
Day 1
- Morning Mashomack Nature Preserve, Kissing Rock
- Lunch Bob's Fish Market
- Afternoon The Ram's Head Inn
- Dinner The Chequit Inn
Stops are grouped by area so each day needs little backtracking. Check opening hours before you go.
Food for you
There are plenty of restaurants where you may want to grab a bite to eat.
Cuisine (tap to filter)
What to ask about, for your diet
Diet labels come from each listing's description and cuisine; “likely” means the cuisine usually has good choices, not a promise. Check with the restaurant. Open the food finder
Photos
Get in
In order to get onto this island, you must take either:
- North Ferry, +1 631-749-0139. Take the Long Island Expressway (I-495) east to the last exit, exit 73. The off-ramp will lead you directly to Suffolk County Route 58 east. After about three and one half miles, County Road 58 will merge into Route 25 east. Continue on Route 25 east for about 20 miles to Greenport. Watch for signs marked "To Route 114 South." These signs will direct you to turn right onto Sixth Street. Drive one block and make your next left on Wiggins Street ("To 114 South"). At the end of Wiggins Street, ferry traffic makes a hard right turn and continues turning right to enter the final staging area. The ferry line takes you away from the ferry, around a loop, and back in line facing the ferry dock and passenger terminal.
Place South Ferry
Take Queens/Midtown tunnel. Take I-495 east to Exit 70. Turn right at the "yield" sign to Route 27 east. Continue on 27 through the town of Bridgehampton. At traffic light, turn left onto County Road 79 through Sag Harbor (4 miles) to stop sign at flag pole. Go left over bridge on 114 north for 3 miles to the South Ferry.
- Westmoreland Airport (49NY), +1 516-354-5310. A small, 1400ft private airstrip for emergency use only.
Get around
The main means of getting around on the island is by car. But you may also walk or ride a bike.
See
See Mashomack Nature Preserve
There is a nice nature preserve that would be a great place to see. It is part of the Nature Conservancy and comprises 1/3 of the island.
See Kissing Rock
Also, there is a huge, well-known rock located at the end of Crescent Beach that was redecorated immediately after 9/11.
- During the summer, once a week, the Perlman Music Camp, founded by world-known violinist Itzhak Perlman, puts on a performance. The students are gifted young people and occasionally Itzhak Perlman conducts the students.
See The Ram's Head Inn
Was the site of the Shelter Island Conference on the Foundations of Quantum Mechanics in 1947. Many famous physicists attended, including Oppenheimer and Feynman. A small plaque commemorates the event.
Do
- This island has many beautiful beaches. Spending a day at the beach would be great to do.
- Also, there are two golf courses and one mini-golf course if you enjoy shooting a game of golf.
- There are also retreats available for groups through St. Gabes and Quinipet.
- Ride bicycles
- Go birdwatching at the nature preserve.
- Rent horses Paard Hill, run by Ellen Lear, daughter of TV Producer Norman Lear, operates these stables which offer lessons for all levels.
- Play a game of tennis at the tennis courts is also an option.
Buy
There are quite a few little shops on the island that are worth checking out. There are some antique shows, gifts shops, specialty shops, and a few delis, etc. There is a newly owned IGA supermarket at 75 North Ferry Road, that offers home and boat delivery. Catering also available 631-749-0382. If needed there are also two banks and two post offices.
Shop
Black Cat Books is a wonderful and classy used bookstore on 114 around the middle of the island. It has a sprawling black couch to rest on and plenty of fiction, art, photo books and more. A great break for those biking across the island on the Hamptons-Greenport route.
Shop Jacks Marine (True Value)
This is a Toy store for all ages. It has been on Shelter Island for over 60 years.
Eat
Eat The Chequit Inn
Good food. Wonderful patio. Great place to meet for a drink. Decent people watching. Great place to stay if you're carless. Azaleas.
There are plenty of restaurants where you may want to grab a bite to eat.
Eat Pat and Steve's
Simple meals. Nothing fancy.
Eat Pridwin
Rustic food and rooms. Cabins ideal for young families. Wonderful salt pool. Spectacular sunsets.
Eat Ram's Head
Lovely place. Perfect for a quiet weekend. Excellent food and service. Superb bartender. Simple but fine accommodations.
Eat Shelter Island Pharmacy
You mean the soda fountain?
Eat Bella Vita
Fantastic Brooklyn-style pizza.
Eat Maria's Kitchen
Organic Mexican stuff
Eat Sunset Beach
A late night spot near the Pridwin. Be cool.
Drink
There are quite a few places to get a drink. All the hotels have a bar and you can also get drinks at The Dory.
Sleep
Hotels
Stay The Chequit Inn
Stay Pridwin
Stay Ram's Head
Bed and breakfasts
Stay Belle Crest Bed and Breakfast
Stay Beach Tree House
Stay The Candlelight Inn
Go next
Villages and Hamlets
- Dering Harbor
- Shelter Island Heights
Nearby
Southold
City / town · 51 listings · 4 mi away
Sag Harbor
City / town · 2 listings · 6 mi away
East Hampton
City / town · 8 listings · 11 mi away
Southampton
City / town · 4 listings · 13 mi away
Old Saybrook
City / town · 40 listings · 16 mi away
Old Lyme
City / town · 21 listings · 17 mi away
Clinton
City / town · 10 listings · 18 mi away
Riverhead
City / town · 21 listings · 19 mi away
My experience
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