Bicyclists love Shelter Island for its laid-back New England atmosphere and gently rolling, tree-shaded byways -- many ending at vest-pocket beaches. To avoid the long weekend ferry lines, savvy day-trippers leave their car in North Haven or Greenport, walk their bikes aboard the boat (or rent them on the island), then meander around on two wheels.
The 8,000-acre island -- whose irregular shape one resident described as a Rorschach inkblot gone mad -- is even more compact than its official dozen square miles when you eliminate marshes and other areas not suitable for bicycling (including the huge Mashomack Preserve, which does, however, provide bike racks).
The preserve offers nature lovers 20 miles of inland trails on 2,039 acres, plus a five-mile round-trip coastal route for canoers and kayakers.
Elsewhere on Shelter Island, sunset viewing is a major evening activity -- and typically, there aren't too many planned daytime events either.
There's a scattering of shops, galleries and places to stop for a meal, snack or picnic fixings. But the overall snail's pace is just fine with the locals -- and with visitors drawn by the island's simple charms.
Your itinerary should include lovely Dering Harbor -- New York's smallest incorporated village (at last count, 28 households on 200 acres) -- and sprawling Big Ram Island, en route to which you'll see huge osprey nests on platforms the phone company built for them atop its poles along the causeway. You also can visit a centuries-old Quaker cemetery off North Ferry Road.
On summer weekends, visitors can tour a couple of historical society properties -- Havens House, the home of William Havens, a member of the First Continental Congress, and the Manhanset Chapel Museum, with changing exhibits in an old chapel -- both in The Center, which is one of the island's two main communities.
Shelter Island's other main community, The Heights, has the island's oldest public building. It's the Chapel in the Grove, noted for its marine mosaic windows. It was built from 1875 to 1876 for guests of a fashionable hotel that was the center of a religious community. The gingerbread-trimmed houses on the streets between the chapel and the harbor also were part of the complex, and were built in the form of a cross.
The earlier history of Shelter Island's is still being probed, and visitors occasionally are invited to view the archeological dig at a 250-acre private estate, once the core of a 17th century plantation that covered the entire island, supplying provisions for two Barbados sugar plantations (and getting from them slave labor).
Last stop: Crescent Beach -- for a soul-melting sunset and, in season, inspiring free tent concerts and recitals almost every evening by gifted students and faculty members at the summer home of the Perlman Music Program (co-founded by Toby Perlman, whose husband, violinist Itzhak Perlman, provides almost full-time mentoring). The 38 students are accepted starting at age 11 and can return annually until they reach 18. In addition to contributing their instrumental specialties -- violin, viola, cello or piano -- to an orchestra, all program members also are part of the school's chorus -- including Perlman.
