Looking for an island excursion? Well, with just a ten-minute hop on the North Ferry out of Greenport to Shelter Island you’ll get just what you're looking for. But don’t be fooled, this piece of tranquility comes well equipt with great restaurants, quaint shops, historical landmarks, a nature preserve, inviting beaches, lively night life, French flair and even some celebrity spotting. We’ve explored the island from all points, both on land and by sea, and here’s what we uncovered.
Shelter Island has a long, rich history. The first summer vacationers arrived on the island in 1871 and formed a resort community known today as Shelter Heights. A stroll through the neighborhood and you’ll find that many of the original, gingerbread homes still remain and are part of the National Registry along with a nine-hole golf course, the Chequit Inn and the Union Chapel. If you’re looking for more authenticity visit the Sylvester Manor Educational Farm situated on 243 acres and dates back to the mid 1600’s. There are cultural events throughout the summer and a working organic farm open to the public. The Havens House, a 1743 farmhouse, now a museum run by the Shelter Island Historical Society, offers up summer activities ranging from Yoga in the Barn to Plein Air painting classes. Don’t miss the lively farmers market held every Saturday morning.
By land – Bike rentals can be had from Piccozzi’s Garage & Bike Shop, located in town, across from Dering Harbor. Please note: The terrain is varied so be prepared for a bit of cardio activity. There’s horseback riding available at Hampshire Farms Riding Center, specializing in English-style horseback riding (is there any other?) and Paard Hill which also offers lessons for all levels
By water – If paddleboarding’s your thing you can rent from Venture Out Sporting Goods. They’ll be happy to drop off and pick up your equipment from any beach, house or other location you might request. Or kayak your way around the island with Shelter Island Kayak Tours. Take a guided tour or venture out on your own just by following the five-mile buoy trail markers. Don’t miss the tiny, Taylor’s Island where you can explore its charming circa-1900 log cabin. Good to know: The island is also accessible by foot at low tide, from Mashomack Nature Preserve – but be sure to watch the changing tides!
Beaches and The Great Outdoors
Accessible only by an unpaved path called Oak Tree Lane you’ll find the secluded Shell Beach, a narrow curl of shoreline that juts into Shelter Island Sound. If you’re looking for where the locals go try Hay Beach off Menhaden Lane, where you’ll find islanders angling for local bluefish. Another favorite is the secluded Fresh Pond, a freshwater pond at the end of Fresh Pond Road, were locals like to go to cool off, though we've heard there are snapping turtles so beware. For non-stop action try Crescent Beach, also known as Sunset Beach where you’ll find water sport rentals and lively entertainment. But if you’re looking for a bit of tranquility head to the Mashomack Preserve, run by The Nature Conservancy. The preserve, which covers about a quarter of the island, has 10 miles of shoreline and 20 miles of hiking trails. Bring your binoculars, it’s the perfect spot for bird watching.
Marie Eiffel offers both a clothing store and home decor store located in Shelter Heights. It’s where you’ll find unique European designers and well chosen, gotta have, items for the home. There’s always a treasure to be found at Marika’s Antiques with an eclectic array of mid-century modern furniture, lamps, flea market finds and outdoor furniture and objects. Dabney Lee, new to Shelter Island, is an airy, new “pop-up” store located on Bridge Street. A great place for stationery, decorative items and accessories. PasParTou, also located on Bridge Street, offers a unique selection of home decor items, fashion accessories, cashmere sweaters, nautical-inspired clothing and vintage nautical items.
Where to Eat
Grab coffee and a breakfast burrito at local favorite, Stars Café, located in Shelter Heights. Reddings Market, located on Bridge Street, is the island’s go-to gourmet market, bakery and café. It’s a good place to fill up a picnic basket for a days outing. Looking for something campy and local then try Bob’s Fish Market, located on N. Ferry Rd. We go for their lobster rolls but if you’re looking to do some of your own cooking then stop in to their adjacent fish market for the local, daily catch. SALT, a casual dock-side restaurant located in Little Neck Harbor serves up their award winning clam chowder and our favorite fish tacos. Looking for the scene and to be seen? Then head to Sunset Beach Restaurant for a late dinner of French cuisine, a bottle of Andre Balazs' Reserve Rosé and plenty of action. Vine Street Café with its simple, farm chic décor, laid back atmosphere, daily specials and amazing wine list makes this a favorite dining spot for locals and visiting Hamptonites. Drop in at the historic Chequit Inn for a casual afternoon bite. Dine al fresco on their umbrella clad patio overlooking the picturesque Dering Harbor. And if you have a bit of a sweet tooth, it’s nothing but ice cream served up at the Tuck Shop located mid-island on N Menantic Road.
Entertainment and Culture
The Perlman Music Center, a summer camp run by violinist Itzhak Perlman. features free weekly concerts throughout the summer. Good people watching and celebrity spotting can be found at Sunset Beach, order up a caipirinha, sit back and enjoy the show. And if you’re looking for some joie de vivre then go for a night-cap along with a rousing game of Petanque at Le Maison Blanche, the island’s homage to everything French.
And on that note - Santé! Et bon voyage!