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Activities and Attractions

Shelter Island Activities and Attractions

You have journeyed from a busy lifestyle and arrived at our wonderful home which is in a secluded setting. You can relax and recharge by lounging at the heated pool, playing croquet on the lawn or walking along the beach nearby.

But when you feel ready to explore, there is more than enough to do “on-island” but where to start? Here is a small list of activities we would recommend:

MASHOMACK PRESERVE – This preserve has been consistently rated as one of the top attractions on Shelter Island. This Nature Conservancy site of approximately 2,100 acres is a must-see with its variety of activities: kayaking, walking trails and bird watching.  Click here to learn more from

SYLVESTER MANOR – This is one of Long Island’s oldest and most historic estates and is on The National Register of Historic Places. Founded by Nathaniel Sylvester in the 1600’s, the current manor house was built by his grandson, Brinley, in 1737. It was until recently the home of the heiress Alice Fiske but upon her death it became The Sylvester Manor Educational Farm. In addition to education and preservation, The Manor offers a complete summer schedule of concerts, dinners and Shakespeare performances.

BEACHES – There is an enormous choice of beaches, starting with “Bootlegger’s Alley”, which is a short stroll from our home. A slightly longer walk away is Sunset Beach and slightly further away is Wade’s Beach, to name but a few. Public beaches have restricted parking access to those other than Shelter Island residents but rental of our home comes with a parking permit.

TENNIS – Shelter Island offers ample opportunity for play: Mousse Drame’ Tennis and Shelter Island Tennis Club (open to the public), both within walking distance of our home. There are also several other public venues on the island.

GOLFING – Shelter Island Golf Club (aka “Goat Hill”) is open to the public; there is also miniature golf at “The Whale’s Tale” in the center of the island. In addition, in Greenport there is also “Island’s End Golf & Country Club” which is open to the public.

SAILING – The Shelter Island Yacht Club has a Youth Sailing Program that is exceptional and offered in 4 or 8 week programs. Camp Quinipet also has a Community sailing program.

BIKING – Hop on a bike and head towards such wonderful destinations as The Heights, Dering Harbor or Ram Island… all full of historical and charming architecture. The island is gently rolling so very conducive to biking.

DINING – When you need a break from relaxed and casual dining on our terrace, there is an abundance of dining options:

  • SUNSET BEACH – chic and sophisticated food in an outdoor setting with, you guessed it, a great spot on the island to see magnificent sunsets.
  • THE PRIDWIN – A visit to Shelter Island won’t feel complete without a visit to the historic Pridwin Beach Hotel where you will get a taste of local music and bands. Wednesdays are a heck of a special where you can get unlimited food and drinks for just $35. Located just a stone’s throw away from Sunset Beach, the gracious old-styled front porch of The Pridwin offers wonderful views of the sunset.
  • SWEET TOMATOES – located in The Heights, this locally-owned restaurant offers traditional Italian cuisine featuring wood brick oven pizzas.
  • THE CHEQUIT – Almost next door to Sweet Tomatoes is The Chequit, which is a charming Victorian Country Inn.
  • SALT – A new addition to Shelter Island in the last few years is Salt Waterfront Bar & Grill, is located at the Island Boatyard. Fun, lively with great food and music.
  • “THE PHARMACY” – How about a hearty traditional breakfast at an old-fashioned pharmacy soda fountain in the center of The Heights.

The above are only a representative sampling of the many dining choices on Shelter Island.


SAG HARBOR – A short ride on the South Ferry will get you to the mainland and nearby Sag Harbor. While known as part of “The Hamptons”, Sag Harbor is different – an old whaling village that is quaint and low-key but with interesting shops, galleries and restaurants. More cultural choices can be found at Bay Street Theater and in book readings at Canio’s. Interesting places to explore include the Whaling Museum and the first Customs House in the US. If you want to explore further, any road heading south from Sag Harbor will take you to Montauk Point which houses the oldest lighthouse in the state, authorized by George Washington in 1792. Southern roads will also take you to all the “Hamptons” towns… E Hampton, Bridgehampton, Wainscott, S Hampton and W. Hampton.

GREENPORT – Take the North Ferry to Greenport, another old whaling village which has a definite New England feel to it. Lots of great restaurants but a perennial favorite is Claudio’s which has great seafood and in the summer, serves at two outdoor venues on a dock overlooking the marina; it is very lively on summer weekends. Head west out of Greenport to visit the numerous vineyards on the North Fork. Head northeast out of Greenport to catch the Orient Point Ferry across Long Island Sound to New London, CT and the rest of New England.

These are just a few attractions and activities you should look into. When visiting Shelter Island, you will quickly find a variety of wonderful activities on and off-island that will keep you coming for years to come.

A NOTE TO PARENTS: My three children spent their summers on Shelter Island and I can’t think of a safer or more wholesome place for children to spend their summer holidays. There are no traffic lights on the island, just a few stop signs and everyone on the island is very mindful of bikers. The island is small so most children from the age of 10-12 take their bikes everyplace. In addition to the activities of tennis, golf and sailing there are other activities offered to day campers ages 4-12 at Camp Quinipet, 5 minutes by car from our home.