In the middle of the bay between the North  and South Forks  is Shelter Island, a quiet retreat of wooded hills, uncrowded beaches, and expensive vacation homes, some of which date back to the Victorian era. Shelter Island has an exclusive air about it, due partly to its moneyed population and partly to the fact that it can be reached only by ferry. The high cost of the very short ferry ride—$9–10 one-way—also helps keep out the hoi polloi.
The island’s first European resident was Nathaniel Sylvester, one of four businessmen who bought the island in 1651. Thanks to Sylvester, the island subsequently became a haven for Quakers fleeing persecution in Massachusetts. Sylvester gave the Quakers shelter—hence the island’s name—and allowed them to practice their religion.
For the day visitor, Shelter Island is the sort of place that’s fun to explore without any particular destination in mind. Many of the roads wander past sun-splashed meadows and bays, dark woods, and historic homes.
Near the North Ferry dock is Shelter Island Heights, filled with steep streets and Victorian-era gingerbread cottages. Across the bay from the Heights is Dering Harbor, boasting a number of impressive mansions along Shore Road. Dering Harbor is the smallest incorporated village in New York State , holding just 32 houses and less than 30 year-round residents (some homes are occupied only in the summer, when the population swells to about 90).
History buffs might also want to stop at Havens House (16 South Ferry Rd./Rte. 114, 631/749-0025, http://shelterislandhistory.org , 1–5 p.m. Fri.–Sun. June–Sept., admission by donation), a 1743 home on the National Register of Historic Places. The five-room house, run by the Shelter Island Historical Society, is outfitted with period furnishings and features a nice collection of antique dolls and toys.
Shelter Island does have one major treasure: Mashomack Preserve (79 S. Ferry Rd., 631/749-1001, 9 a.m.–4 or 5 p.m. daily, adults $2, children $1), operated by the Nature Conservancy. Occupying nearly a third of the island, the preserve spreads out over 2,000-plus acres of oak woodlands, marshes, freshwater ponds, tidal creeks, and shoreline. Within its confines is one of the East Coast’s largest concentrations of nesting osprey, along with everything from ibis and hummingbirds to harbor seals and terrapins. Nature trails and hikes 1.5–11 miles in length meander through the preserve. The entrance to the preserve is located about a mile from the South Ferry dock.
Built on bluffs overlooking Coecles Inlet is the 1929 Ram’s Head Inn (Ram Island Dr., 631/749-0811, www.shelterislandinns.com/ramshead , $150–350 in summer, with breakfast, about a third less off-season), boasting its own private beach, small boats, tennis courts, restaurant, and wide porch complete with wicker furniture. Most of the 17 rooms are filled with lots of light and simple antiques. Lunch and dinner (average entrée $20) consist of seasonal, local ingredients served in a high-ceilinged room hung with paintings.
In Shelter Island Heights is the friendly, turn-of-the-century House on Chase Creek (3 Locust Ave., 631/749-4379, www.chasecreek.com , $110–215 d summer, $65–175 d off-season), offering three comfortable guest rooms. Also in town, find the Dory (Bridge St., 631/749-8871), serving simple seafood dishes on an outdoors deck during the summer.