Tucked neatly between the two forks of our Long Island, the North ending at Orient and the South ending at Montauk, is a hidden gem. The nearby getaway that is Shelter Island has remained one of Long Island’s best-kept secrets and it’s no wonder; Shelter Island, like many of the sections of Fire Island, is accessible only by riding a ferry. However, unlike Fire Island, visitors are able to bring their vehicle across with them. This allows Shelter Island to act as a conduit for the vacationer looking to get the most out of their trip, providing drivers a shortcut from one fork to the other as well as a stunning stop along your route.
The factors that have kept Shelter Island from becoming widely known have also allowed it to maintain the same tranquility and natural beauty it has enjoyed for hundreds of years. The five-mile-wide island also offers visitors an enticing array of activities, ranging from golf, tennis, biking, fishing, to dining in top-notch restaurants. It provides a peaceful atmosphere, though busier in the summer months, where one may explore art galleries and a spectacular nature preserve, or swim at some of the most magnificent beaches in the world. While it feels like it’s in the middle of nowhere, Manhattan is only a little more than two hours away.
Ferries travel to Shelter Island from two villages: Greenport on Long Island’s North Fork and Sag Harbor, on the South Fork. During the summer, ferries leave from each point every 10 to 20 minutes, though service also continues during the rest of the year. While cars are permitted on both ferries and are the best way for touring the island, pedaling a bicycle is another great way of getting around. On-road bike route 114 is a shared road that spans the north to the south ends of the island with connecting routes to other paths. It’s quite a walk on foot, but if hiking is your goal the nearby nature preserve has some scenic winding paths.
The island is a haven for ospreys, and osprey nests are such an important part of the scenery that some telephone poles have platforms to accommodate! One of the most outstanding natural sites in all of New York can also be found on this tiny island: Mashomack Preserve. This tranquil ecosystem is framed by ten miles of coastline and consists of nearly 2,100 acres, one third of Shelter Island. It Encompasses a diverse range of habitats, including interlacing tidal creeks, woodlands, fields and grassy meadows, pine swamp, and coastline, and also contains extensive salt marshes. In addition, 1,400 acres of upland oak and beech forest have been left to develop into an old-growth forest, a scarce habitat here in this part of the U.S. Animal species thrive here including two endangered birds, the piping plover and the least tern, as well as many rare plants.
The history of Shelter Island starts in 1652, when a sugar merchant from Barbados named Nathaniel Sylvester acquired sole title. By the mid-1700’s only 900 islanders populated the land, and it wasn’t until 1871 that Shelter Island’s present-day character began developing. The area in which they settled, Shelter Island Heights, became a charming resort community dotted with distinctive houses designed by prominent architects like Frederick Law Olmsted, the designer of Central Park. A second period of development, after 1880, resulted in larger homes in the Stick, Queen Anne, and Colonial Revival styles, featuring elaborate porches, scalloped shingles, and clapboard siding. While most are private houses that can only be viewed from the outside, the charm of Shelter Island’s communities make a walk, a drive, or a bike trip through its meandering streets a captivating experience.
The oldest building here, Chapel in the Grove, was constructed in a natural amphitheater in 1875. Its marine mosaic windows are the handiwork of local artist Walter Cole Brigham. Ecumenical services are still held in the chapel during the summer. An architect and builder, Gabriel Crook, built Crook House in the Greek Revival style between 1820 and 1849. Another well-known builder, Charles Washington Reeve, constructed Augustus Keller House, which has been used for filming many movies. The Gingerbread House is a dollhouse-like Victorian complete with a gabled tower, arches and curves, and of course gingerbread trim. A local man, Frederick Chase, built it for his daughter in 1875. Advertising executive Shorewood Ward built Artemas Ward House, bringing artisans over from Italy to create it.
Not surprisingly, Shelter Island’s natural beauty has inspired artisans and artists alike. Haps Ironworks features the metal sculpture of native artist and blacksmith Hap Bowditch, Jr., as well as paintings by Louise Tuthill Green. The Peggy Mach Gallery displays the paintings and sculptures of contemporary artists.
On Shelter Island, the catch phrase for shoppers is quality, not quantity. This naturalistic enclave is hardly a haven for commercialism, and the distinctive shops that dot the island have a special flavor all their own. For those who appreciate times gone by, Fallen Angel Antiques is a “must”. For more modern merchandise, visitors will enjoy browsing in Marika’s Eclectic Boutique, Cornucopia, and The Whale’s Folly. And for a fun and truly old-fashioned shopping experience, no place beats Bliss’ Department Store, a small town five-and-dime with creaking wooden floors that sells everything from needles and thread to overalls to beach chairs.
The island’s modest size imposes no limits in terms of the types of eateries available. Seafood is featured at restaurants like Bob’s Fish Market and Commander Cody’s Fish Shoppe. Creative cuisine is the specialty at Michael Anthony’s at the Dering Harbor Inn. Choices like sweet potato ravioli in ginger cream sauce with pine nuts make it a favorite with both locals and visitors. Le Maison Blanche began as a Victorian inn, originally built in 1886, and the Pridwin Hotel features a dramatic dining room that overlooks Peconic Bay. The elegant Ram’s Head Inn overlooks Coecle’s Harbor and Gardiner’s Bay, and the Victorian Chequit Inn, built in 1872, capture the hideaway’s rustic, seaside flavor. For a more casual dining experience, visitors may prefer More the friendly atmosphere of Alfred’s Port Tavern & Eatery, which features burgers, pasta, and seafood, or The Dory, with outdoor deck dining.
Given Shelter Island’s Victorian atmosphere, its numerous comfortable bed and breakfasts fit right in with the landscape. Their names alone conjure up images of white wicker furniture, ruffled curtains, and generous farm-style meals served in a sunny breakfast room: Azalea House, Beech Tree House, Candlelite Inn & Guest House, Belle Crest House, and House on Chase Creek, to name just a few.
The island’s hotels are just as charming. Rather than offering cookie-cutter glitz, they, too, are housed in wooden Victorian buildings, with charming features like large porches and fireplaces. The Chequit Inn and the Ram’s Head Inn echo the same informal feel as the restaurants they feature, while the Pridwin Resort Hotel on Shelter Island Bay has both rooms and efficiency apartments. The Dering Harbor Inn features cooperative apartments that are available for weekly or seasonal rentals, with amenities like a salt water pool, tennis courts, and a marina.
All in all, Shelter Island is worth the trip. It is just the right amount of secluded, and connects two of the most frequented sections of Long Island. Its serenity provides the perfect location for a day trip if you’re looking to escape, or even a lengthier stay to clear your head. The concentration of the island’s historical homes and shops make can make even the shortest walkabout a unique pleasure, offering sights you won’t catch anywhere else, so pay a visit some time and see what is happening on the five mile island.