shelter island, bootleggers alley, beach
The beach at Bootleggers Alley.

Summer Getaway: Shelter Island

June 01, 2009
by Sarah Amandolare
Shelter Island is a natural haven on New York’s Long Island. Outdoor enthusiasts flock to Shelter Island’s beaches and nature preserve, while active travelers can glimpse the scenery from the seat of a bike or in a kayak. Learn why this dreamy waterside destination is such a coveted summertime spot.

Shelter Island's History

About a century ago, farming was the main source of income for most Shelter Island residents; fishing was also a livelihood, according to With only 2,500 full-time residents, the land was what mattered most: “8,000 acres of land, marsh, and mist nestled between the North and South Forks of Long Island.”

The “sheltering effect” is due to Gardinerís Island located to the east. Learn more about Shelter Island’s first settlers and land division, and how life there has progressed over the past several decades.

How to Get to Shelter Island

New Yorkers are in luck, as Shelter Island is easily accessible by ferry from two locations on Long Island: Greenport, at the north end, and Sag Harbor, at the south end of the island. To reach the ferries, take the Long Island Railroad from Penn Station in Manhattan. Those travelers who will be flying in from out of state must still take a ferry to reach Shelter Island. The north end is more convenient, located within walking distance of a relatively bustling stretch of eateries and shops, including Piccozzi’s, a garage and bike rental shop.

Getting Around by Bike and Car

The name Shelter Island suggests something small and secluded; the secluded part is true, but the island is actually quite large, covering 8,000 acres.

To get around easily, it’s advisable to have a car; you can bring it with you on the ferry ride over. However, on a daily basis, a bike is just as essential, as it allows you access to side streets leading to quiet beaches, and generally allows for a more intimate perspective of the landscape.

Use Google Maps to plot your course, and glean cycling suggestions from Newsday’s Lauren McSherry: She presents a long and short route and describes stops along the way, such as Bootleggers Alley and the historic Shelter Island Heights area.

According to McSherry, Bootleggers Alley refers to the island’s “long history of smuggling,” which harkens back to the 1600s when sugar merchants from Barbados bought the island and began harvesting oak trees for use as rum-shipping barrels. Bootleggers Alley was also in heavy use during Prohibition.

Shelter Island Nature

Biking offers great views of Shelter Island’s lush, green landscape, but there’s even more to see at Mashomack Nature Preserve, an area covering one-third of the island. The preserve has been protected by The Nature Conservancy for more than 25 years, and features unusual ecosystems: “interlacing tidal creeks, mature oak woodlands, fields, and freshwater marshes,” in addition to 10 miles of coastline. The preserve is favored by ospreys that build massive nests high in the treetops.

Kayaking is another interesting and active way to see Shelter Island’s natural abundance. The Coecles Harbor Marine Water Trail, which has been in use since 2001, mimics “a hiking trail” and “has a map at its trail head,” according to the Shelter Island Reporter. Along the trail, markers with The Nature Conservancy’s oak leaf emblem lead the way.

Learn about kayak rentals, and guided and self-guided tours from the Shelter Island Kayak Tours Web site. Tours are led by Jay Damuck, an experienced kayaker who “caters to each paddlers personal pace and schedule,” according to the site. Beginners are welcome, and fishing and bird watching are enjoyed along the route.

After a long day of biking and kayaking—and hopefully some beach time—relax for the night at a historic Shelter Island inn, such as the Ram’s Head or Chequit Inn.

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