Escape to Shelter Island: 5 Insider Tips

Tucked between the North and South Forks of Long Island’s fabled East End, Shelter Island  was a safe haven for generations of seafarers who sought refuge from the ravages of the North Atlantic.

Today it’s a haven from the havoc of modern life with a very family oriented and pet-friendly vibe.  Shelter Island has yet to install a traffic light but there is no mistaking its laid-back summer sophistication.  Here are some tips as you plan your escape …..

First, to get your bearings: The main town is Shelter Island Heights, near the North Ferry across from Greenport. It is the original community and known for its Victorian architecture. At the other end of the island, about seven miles away, is the South Ferry linking Shelter Island to the South Fork of Long Island, just outside Sag Harbor.

Screen Shot 2016-07-05 at 11.40.28 AM









1. Food & Shelter:  Happily, these essentials are plentiful on Shelter Island. Small hotels and B&Bs reflect the look and feel of the island. With a limited number of rooms, they tend to be booked fully on summer weekends. Consider September when the crowds are gone!IMG_0231

I like, in particular, the historic Chequit,
named to the Conde Nast Traveler’s “Hot List” for 2016. It’s in Shelter Island Heights, a short drive (or long walk) from the North Ferry.The in-house Red Maple restaurant is excellence in casual fine dining. Have whatever fish they’re serving – it was swimming off Montauk that morning.


The Euro-chic Sunset Beach hotel brings a bit of St.Tropez ooh-la-la to Shelter Island, leveraging its location by providing a sea view and a small private deck for each of its twenty rooms.

IMG_0291The bar and restaurant extend the Euro-chic ambiance with aprés-beach cocktails and dinner overlooking…. yep, a beautiful sunset sinking into the water. Don’t miss the upstairs deck at 6 P.M. for Mojitos and people-watching. Move on to the sand-floor bistro for moules, frites and a rosé; you’ll leave feeling you’ve been to the Côte d’Azur.

If your tastes veer toward  New England-coast-shingled-house, The Ram’s Head Inn will make you feel a lot further than 90 miles from New York City. Its bluff-top setting is on the “far” side of Shelter Island is gorgeous. An attentive staff will help make your stay as active as you want, and lovely on-premise dining means you never have to leave.

Looking for a B&B?  I highly recommend Seven, a sophisticated  boutique B&B outside Shelter Island Heights. It’s luxury wrapped around a charming early 19th-century farmhouse with an impressive modern art collection on the walls. The perfect weekend get-away spot, close to everything yet not hemmed in by anything.

Of course, for a longer stay a house rental is probably your best bet. The usual suspects, AirBnB and VRBO/Home Away, are good resources.

Other dining spots of note which specialize in locally sourced, seasonal ingredients and are very, very good: Vine Street Cafe,  and 18 Bay.

A spot where seemingly the entire summer community convenes for a sandwich, take-away food or picnic fare – is  Marie Eiffel’s Market in the Heights.IMG_0302







IMG_0195An iced coffee on the market’s back deck, on a summer’s day, overlooking Dering Harbor. Could this be perfection?













There are many more options along the casual dining spectrum, including the  60’s era lunch counter/soda fountain at the Shelter Island Heights Pharmacy.  Best. Breakfast. In.Town.  On many levels…..

Before that iced coffee, check out the breakfast.

2. Beaches and Boat Ramps:  There are 5 “official” town beaches on Shelter Island and each requires a parking permit purchased for the day, week or month.  Two of the beaches (Wades and Crescent) are “bathing” with lifeguard stations and comfort facilities. One hidden gem is Fresh Pond which is a lovely place for a paddleboard or a kayak.

This slideshow requires JavaScript.


Note: The parking permit workaround is the lovely strip of beach at the end of Bootleggers Alley…. no parking permit required. And, there’s a boat ramp – here are others around the island.

Screen Shot 2016-07-09 at 11.04.48 PM IMG_0252

Bootleggers Alley is not an “official” beach so it offers no amenities other than peace and quiet and the general absence of crowds.





Our friend Digby is on regular patrol at Bootleggers Alley, along with his pals.













3. The Cure for Island Fever: Unlike other island destinations in the Northeast (think Martha’s Vineyard, Nantucket, Block Island), Shelter Island is readily accessible to the “mainland” should the island’s 8,000 acres prove too confining.

However, the traffic on the South Fork, especially toward the Hamptons, can be brutal. That said, going to Sag Harbor mid-week shouldn’t ruin the vacation karma.  I like The American Hotel (especially in the “off-season”)  or the porch of Baron’s Cove  for dinner.














In Greenport, favorite restaurants are Scrimshaw and Noah’s.  The huge plus of going to Greenport for dinner is leaving the car at the Shelter Island ferry lot; the restaurants there are walkable from the Greenport dock.

4. Beyond Beaches — Things to Do Across the Fun Spectrum:

Biking, Kayaking 


Piccozzi’s, in Shelter Island Heights, which doubles as the gas station among other enterprises, does a brisk bike rental business with a fleet of well-maintained bikes. They also offer a repair service – the only one, to my knowledge, on the island.




Shelter Island is wonderful for kayaking;  rent all the equipment you need to go off on your own or take part in arranged tours –  a great experience for all ages!



The Shelter Island Golf Club – or “Goat Hill” to the locals, is a public, 9-hole course just outside the Heights.  It is beautifully situated upon the highest point with stunning views. There is a lovely clubhouse, open April – October so even non-golfers can enjoy the 360º view over lunch or a drink.




For miniature golf aficionados, check out The Whale’s Tale because who doesn’t want ice cream at the end of a round??

Perlman Music Program Concerts


The Perlman Music Program, founded by Itzhak Perlman’s wife to cultivate gifted young string players, is the cultural heart of Shelter Island. Weekly concerts in July and August showcase the work of students, faculty and visiting artists.










Shelter Island Baseball



The pride of Shelter Island summer baseball and the 2015 Hamptons Collegiate Baseball League Champions. It’s a go-to event with hot dogs, soda, and eager college talent hoping to be spotted by Major League scouts. These are serious players and a ton of fun to watch.



Shelter Island’s Legacy

Sylvester Manor Educational Farm – Sylvester Manor is where the past and present come together to celebrate, educate and plan for the future. The rich warp and weave of the Sylvester family, who settled on Shelter Island in the mid-17th century, reflects the history and evolution of our country over the centuries.

Now, the 10th generation descendant of the founding family has transformed this former “provisioning plantation” into a non-profit organization guided by a mission to “cultivate, preserve, and share these lands, buildings, and stories- inviting new thought about the importance of food, culture, and place in our daily lives.”  Check out the events throughout the summer and fall.

Mashomack Preserve


About a third of Shelter Island is undeveloped and managed by the  Nature Conservancy’s  Mashomack Preserve . It includes miles of paths for year-round hiking, birding, or just getting in the groove with nature.   The marshes, wetlands, and beaches have remained untouched in the 400 years since Shelter Island’s first European settlers took up residence.

Warning: deer ticks, which can carry Lyme Disease, abound in Shelter Island’s beach grass and in wooded areas. Take caution especially during warm weather. Ticks are the serpents in our Eden. 





5. And now for the book recommendation

As you know, I’m all about reading up on a place before you visit, to enrich the travel experience and provide a cultural or historic context. The Manor: Three Centuries at a Slave Plantation on Long Island by local landscape historian Mac Griswold paints a picture of the history of Sylvester Manor that reflects the larger American narrative, and the role of place in that narrative. Highly recommended.

Do you have a favorite Shelter Island story?  Please share in the comments!



©3 Score & More, 2016



3 Replies to “Escape to Shelter Island: 5 Insider Tips”

Comments are closed.

%d bloggers like this: