Shelter Island is a rocky, hilly, 8,000-acre parcel of land located between the North and South forks of Long Island that is accessible by train, bus, or car, followed by a 10- to 15-minute ferry ride. Route 114, a country road that runs between the North and South ferries, bisects the island.
Most Shelter Island neighborhoods don’t have real boundaries, but each has its own personality. Some have deeded beach rights, a property owners’ organization and even water or sewer service. But most of the 2,400 year-round residents identify first as islanders no matter what neighborhood they call home.
Shelter Island Heights
This cluster of charming Victorian and farmhouse-style homes on tiny lots extending from the North Ferry landing and bounded by Chase Creek, Dering Harbor and Greenport Harbor was conceived as a planned community when it was built in the 1870s. Featuring homes with porches, gingerbread woodwork, tiny yards and looping streets laced with walking paths, the Heights was designed for vacationers who arrived on the island by foot. Restaurants, shops, a pharmacy and hardware stores are all within easy walking distance of most homes in the Heights. A beach club, tennis courts and public golf course are an integral part of the neighborhood and are all easy to reach by foot.
As you approaching Shelter Island on the North Ferry, it’s hard to miss the group of enormous mansions lining the eastern shore of the Village of Dering Harbor. One of the smallest villages in New York State, Dering Harbor was formed in 1916. With just a handful of year-round residents, it is very, very small — and the homes are very, very big. Some look as though Stanford White might have designed them. In fact, White did once design a Dering Harbor home, but the owner, who wanted more space for recreation, tore it down decades ago.
Situated in front of the American Legion Hall on Route 114 is a traffic circle, and radiating from that circle is an area known as “The Center.” Many year-round islanders live here, where they are within walking distance of the Shelter Island School, post office, public library and Town Hall. A grocery store, liquor store, fitness center, bank and ball fields that host collegiate-league baseball in the summer and school sports the rest of the year are all within a quarter-mile of each other. Some of the island’s best casual restaurants are in this area, including a diner called The Islander and a Mexican place called Maria’s Kitchen. Meanwhile, 18 Bay is an ambitious restaurant that draws diners from all over the East End. The Presbyterian church also hosts a year-round musical program of concerts. Houses in The Center are mostly small and located on modest lots that, by Shelter Island standards, are reasonably priced.
At the southern end of Menantic Road is a group of four scenic streets lined with water view homes on large lots. Developed by builders from Montclair, N.J., the neighborhood became known as Montclair Colony. Nearby is the Island Boatyard and SALT, a restaurant with a lively bar and lovely dining area right on the water.
Hilo Shores was developed on a series of steep hills near West Neck Bay. Named for the terrain, many of the homes have lovely views of the Bay and the hills make for a charming series of twists and turns on roads through the wooded neighborhood.
Westmoreland is a peninsula with an airstrip on one side and West Neck Creek and West Neck Bay on the others. It is an idyllic neighborhood of very large lots and lovely homes, which have somehow retained a yesteryear vibe of farming and country living. Westmoreland Drive cuts right down the middle of it. Along the way, horses graze on green fields, and the airstrip — which is really just a very long field of grass and wildflowers — runs beside fine homes and plenty of open space.
Silver Beach is a large, almost completely flat area including everything beyond Westmoreland between West Neck Creek and Shelter Island Sound. This neighborhood is largely free of the “McMansions” that have gone up elsewhere on the island in recent years, with spacious homes appropriately sized for their lots. Silver Beach is blessed with excellent beaches: one at the end of Bootleggers Alley that’s great for walking and beachcombing, and another called Shell Beach, a strip of land that extends for a mile into West Neck Harbor. Shell Beach is the best place on Shelter Island to find seashells and see piping plovers, endangered shore birds that nest there.
Big and Little Ram islands
Owned for many years by the Tuthill family, these hilly islands are connected to each other, and the rest of Shelter Island, by two scenic causeways. Ospreys nest atop telephone poles, seals sun themselves on rocks near the shore, and views can be taken in south over Coecles Harbor and north across Gardiners Bay. Largely undeveloped until the 1950s, both islands are now lined with large homes on large lots, many with jaw-dropping water views. The Ram’s Head Inn has commanded the top of the first hill on Big Ram Island since 1929. The only commercial business on the Rams, it’s the most scenic spot on Shelter Island for a sunset drink on the lawn or a celebratory dinner.
A sign near the intersection of Gardiners Bay Drive and Ram Island Road now welcomes you to Hay Beach, but in the late 19th century this was an industrial site known as “Bunker City” where menhaden — a small, oily fish that is remarkably odiferous when heated — was processed into oil and fertilizer. The site of some of the most architecturally significant homes on the island, Hay Beach contains a web of roads through heavily wooded properties. Homes on the water side of Gardiners Bay Drive have magnificent views east to Gardiner’s Island, with Montauk visible on clear days.
The beach at the end of Menhaden Lane, usually called Hay Beach, is arguably the prettiest on the island and is much loved by open-water swimmers, who splash up and down the length of the beach on warm afternoons. Another beach at the Hiberry Lane town landing is quiet and great for sunbathing.
Heading south on Midway Road leads to family-friendly Wades Beach, and from there everything south of Midway is the neighborhood of Shorewood. Artemus Ward Sr. was a well-known and wildly successful businessman in the early 20th century who owned 275 acres here. The remnants of barns and gardens from his estate are still visible. This quiet and lovely neighborhood is heavily wooded; houses near the shore from Wade’s Beach around Wards Point have views south across to the South Fork and Noyak.
South Ferry Hills
At the southern end of Route 114, as the road approaches the South Ferry, a sign at Thompson Street marks the entrance to South Ferry Hills, an enclave of appealing homes on modest-sized lots. The hilly terrain offers glimpses of water and of the 2,000-plus acres of Mashomack Nature Preserve, located just north of the neighborhood. A community beach and boat launch at the very end of Thompson Road has a private and secluded feel, though people from all over the island come here to relax.