Shelter Island Driving Tour
~12 mi
Total Distance
~90 min
With Stops
10
Points of Interest
0
Traffic Lights
Before You Start
This loop begins at the North Ferry landing on Shelter Island and works clockwise around the island before ending at the South Ferry dock. You can just as easily start from the South Ferry side and follow the route in reverse.
The entire island runs on two-lane roads with a 30 mph speed limit. There are no traffic lights, no highway ramps, and no rush hour. Pull over anywhere that catches your eye — you will not hold up traffic.
Gas up before you board the ferry. There is one gas station on the island at the corner of Route 114 and North Midway Road.
The Route
10 Stops Around the Island
Stop 1
North Ferry Landing
Your tour begins the moment you drive off the ferry from Greenport. Turn right onto Route 114 and head toward Shelter Island Heights. The road is lined with old-growth trees and stone walls — a preview of what the rest of the island looks like.
Stop 2
Shelter Island Heights
This Victorian neighborhood was built as a Methodist campground in the 1870s and is now on the National Register of Historic Places. Walk the narrow lanes to see 141 original gingerbread-style cottages. Visit the Union Chapel, known for its striking marine mosaic windows by William Cole Brigham.
Stop 3
Crescent Beach
Continue north to this protected bay beach — one of the best on the island. Calm, shallow water makes it ideal for families and paddleboarding. Lifeguards are on duty in summer, and there are restrooms and a snack bar. No dogs from Memorial Day through Labor Day.
Stop 4
Dering Harbor
Head south along Shore Road for postcard views of the harbor. Dering Harbor is one of the smallest incorporated villages in New York. Pull over near The Chequit — the historic inn overlooks the water and has been welcoming guests since the 1870s.
Stop 5
Havens House
Built in 1743, this is the oldest surviving house on the island. Over the centuries it served as a store, tavern, school, post office, and town meeting hall. Now operated by the Shelter Island Historical Society, it is listed on both the State and National Registries of Historic Places.
Stop 6
Sylvester Manor
A 243-acre working farm that has been continuously operated since 1651 — making it one of the oldest in the country. Walk the grounds to see the 1737 Manor House, a restored 19th-century windmill, and the Afro-Indigenous Burial Ground. Seasonal farm stand with fresh produce.
Stop 7
Mashomack Preserve
The crown jewel of Shelter Island. This 2,039-acre nature preserve covers nearly a third of the island and is managed by The Nature Conservancy. Ten miles of coastline, tidal creeks, mature oak forests, and nearly 200 bird species. Choose from four marked trails ranging from 1.5 to 11 miles.
Stop 8
Shell Beach
A quiet, unspoiled stretch of shoreline on the island’s southeast side. True to its name, the beach is carpeted with shells. It is also an important nesting habitat for piping plovers and least terns — keep an eye out for marked nesting areas. No dogs Memorial Day through Labor Day.
Stop 9
Wades Beach
On the island’s southern shore, Wades Beach has the softest sand and gentlest waves on Shelter Island. Lifeguards are on duty in season. The open-air pavilion makes a good spot for a picnic. From here it is a short drive to the South Ferry dock.
Stop 10
South Ferry Landing
The tour ends at the South Ferry dock on the island’s southern tip. If you are heading to the Hamptons, the South Ferry crosses to North Haven near Sag Harbor. If you are heading back to the North Fork, simply drive north on Route 114 — the same road you started on — back to the North Ferry. The cross-island drive takes about 10 minutes.
Driving Tips
Speed limit: 30 mph island-wide. Some residential lanes drop to 20 mph.
Fuel: One gas station, at Route 114 and North Midway Road. Fill up on the mainland if you can.
Parking: Free everywhere. Beach lots fill up on summer weekends by late morning — arrive before 10 am.
Biking: Route 114 is also NY State Bicycle Route 114. Expect cyclists sharing the road, especially on weekends.
Cell service: Coverage is spotty on the eastern half of the island. Download directions before you go.
Groceries and supplies: The town center near the intersection of Route 114 and Grand Avenue has a handful of shops and a general store.
Getting to Shelter Island
Every visitor arrives by ferry. Check the schedules and fares before you go.
