Shelter Island lets you relax off the grid in a number of soul-satisfying ways. Spend the day getting lost on a bike, kayaking in secret coves or hiding behind a beach read. Or venture out to a 2,000-acre wildlife preserve or back in time to a historic former slave plantation.
Shelter Island is a sparsely-populated 12-square-mile township wedged between the North and South Forks. The more adventuresome can sail or paddle a kayak to Shelter Island, but most visitors take the ferry from Greenport (North Ferry Co., 631-749-0139, northferry.com) or North Haven on the South Fork (The South Ferry Company, 631-749-1200, southferry.com).
The North Ferry docks at Shelter Island Heights, a historic hub of lodgings, restaurants and shops. Route 114 — also known as North Ferry Road and South Ferry Road — is the main drag. Sit down and dine at one of the smattering of local independent restaurants such as The Islander (631-749-1998, theislandersi.com), or pick up a chocolate croissant or artisanal cheese at the French-inspired Marie Eiffel Market (631-749-0003, marieeiffelmarket.com).
Shelter Island’s Victorian house-lined shady lanes – and 35 mph speed limit – invite a leisurely bike ride. Bring your bike on the ferries, or rent from Piccozzi’s Bike Shop (631-749-0045, jwpiccozzi.com). The tiny Shelter Island Craft Brewery serves post-ride snacks such as fresh craft beer and pretzels. (631-749-5977, shelterislandcraftbrewery.com). Side trips include the Sylvester Manor Educational Farm, a onetime slaveholding plantation reborn as a nonprofit organic farm and arts and education center. (631-749-0626, sylvestermanor.org). Fashion your own triathlon with a paddle at Shelter Island Kayak Tours (631-749-1990, kayaksi.com) or a hike at Nature Conservancy’s 2,039-acre Mashomack Preserve. (631-749-1001, nature.org)
Or just relax on a blanket at Crescent Beach or Wades Beach, exclusive spots for sunbathing and lifeguarded swimming. Beach stickers are available at Shelter Island Town Hall (from $25/day, 631-749-1166, shelterislandtown.us).