"Shelter Island, in the language of its original inhabitants, the Manhansets, meant “an island protected by islands.” It lies between the North and South Forks of Long Island, which was declared a peninsula after a court fight in 1985. But geological particulars aside, the sentiment and the feeling of protection from overcrowding and rough seas remains to this day. Its recorded history dates to the 17th century and the Caribbean sugar trade. It is reachable only by ferries, from Greenport on the North Fork and North Haven on the South Fork, private boats and seaplanes. The island — about 12.5 square miles of wetlands, forests, beaches, golf courses, marinas and homes ranging from modest cottages to the grandest of mansions — is home to about 2,400 year-round residents, according to the 2010 census — a number that grows to 12,000 by various estimates in the summer. Still, with one-third of the island set aside as a nature preserve, it remains a bucolic place beloved by long-timers and newcomers alike."
Lodging: Seven, a bed-and-breakfast, is just up the hill from Crescent Beach at 7 Stearns Point Road. Once a farmhouse, built in 1902, it features kinetic sculptures and a contemporary art collection. Double rooms start at about $355 a night during the summer season; sevenonshelter.com.
"Take a hike at Mashomack Preserve, which is protected from development by the Nature Conservancy. The preserve has more than 2,000 acres of forests and wetlands, threaded with trails that range from 1.5 miles long to nearly 11. There is a renovated manor house, scene of social events in the summer, and a variety of environmental programs for adults and children."
"For many visitors, the two-story party scene at Sunset Beach, the hotel and restaurant on Shore Road, is not to be missed. Some arrive by boat — or more accurately, by yacht — from the Hamptons, anchoring off the beach for late-night mingling over food and drinks. During the day, under colorful umbrellas, hotel or restaurant guests can order drinks, play beach volleyball or get a massage on the beach. For information on seaplane flights from Manhattan, visit shorelineaviation.com."
"Take in a concert at the Perlman Music Program. The center — on land that was once Dr. Pettit’s Camps and then the Peconic Lodge — was created in 1994 by Toby Perlman, the wife of the violinist Itzhak Perlman. It provides a summer of intensive musical training for talented, young string musicians. Evening performances of classical music are popular among locals and visitors alike. Mr. Perlman himself makes occasional appearances. Most of the events are free or a small donation is suggested."
"For some, the lovely, protected beaches are the real reason to come here. Pick up sandwiches at the Marie Eiffel market across from Piccozzi’s Bike Shop and head to Wades Beach on the south side of the island. Shelter Island Kayak, which has been operated by Jay and Patti Damuck for 25 years, offers two-hour kayak tours from Coecles Harbor through nearby waterways ($60 for adults). They will also transport kayaks and paddleboards to the beach of your choice with a little advance notice. (Kayak rentals are $30 for a two-hour minimum; paddleboards, $30 an hour.) Wades, with picnic tables, lifeguards and a restroom, is a family favorite. The adjoining Dickerson Creek is a treasured spot for clamming at low tide and watching the tiny fiddler crabs burrow into the sand. (If you want to dig for edible clams, you’ll need a shellfish permit from the town hall.) Across the way is a hook of land known as Shell Beach, accessible by water or by the narrow, sandy Oak Tree Lane."
"Find a seat on the porch of the Shelter Island Country Club and enjoy views of Peconic River and Dering Harbor from one of the island’s highest points. The country club, also known as Goat Hill, is a public nine-hole golf course established in 1901 ($25 for nine holes, weekends). The restaurant, now renamed the Flying Goat, and bar are favorite gathering places for locals."