Fifty years ago I thought I'd live on Shelter Island one day. That never happened but I do sail around it almost eight months a year. Therefore the island the locals call "The Rock" has a special place in my heart. I remember my first ride on a South Ferry and the excitement I had as a young teen getting out to feel the breeze as we went from North Haven to South Ferry. I still feel like a kid every time I ride that ferry to this day.
For a while (three years) I actually had a Friday weekly delivery route all over Shelter Island. I recall being the only vehicle on the South Ferry as it was snowing heavily in the winter and yes, I have experienced the horror of arriving and seeing a long line of cars in peak summer. But once on the ferry I feel like I am going to someplace special because it is. I always find solace of spirit when I am on "The Rock." There is a real magical shelter for one's soul on Shelter Island.
The highest spot on Shelter Island is only 56' above sea level. The island is all of a total of 29.11 sq. milesou of which more than half is water (16.92 sq. miles). The views along its coast include Bug Lighthouse, Greenport/Orient/Southold/Sag Harbor/North Haven/Cedar Point/East Hampton and Gardiner's Island. The beauty of any one of these views is compounded by the beauty of its unique historic and quaint harbors, such as West Neck Harbor, Coecles Harbor and Dering Harbor.
What I found amazing are these facts. Within the roughly less than 2,500 full time population of Shelter Island are still reportedly "numerous" Shelter Island residents with family roots dating to families on Shelter Island during the American Revolution. Even more amazing is there are actually some summer residents who are "5th generation seasonal visitors!"
My favorite tourist thing on Shelter Island is a Saturday night at Sunset Beach
, the trendy outdoor bohemian resort/restaurant/bar/nightspot. Very pricey with $17 mixed drinks but what a place to spend at least one summer weekend evening having fun kicking back. For more of a blue-collar experience there is the Dory on Route 114 in Dering Harbor. This place is as real a watering hole as one can be. The burgers are good and the place is affordable. There are many wonderful restaurants in season on the island, and my favorite is the Ram's Head Inn. It has amazing space with atmosphere, grace along with great views of Coecles Harbor. I think the Marie Eiffel Market (Dering Harbor) produces the best lobster roll on the East End, and yes, I have run in many of the Shelter Island Runs, now celebrating their 40th year. In fact, I may have the overall worst career time record for a person who ran in eight or more events over two decades. I still have a few of the tee-shirts!
What I love to do is drive to Shelter Island via the ferries (North Ferry) from Greenport or (South Ferry) from North Haven. I used to drive out of my way to take my children on the ferries to experience that short ride! Now I actually sail to Shelter Island. I sometimes dock at the town dock in Dering Harbor or tie on to the Rams Head Inn
dock in Coecles Harbor, and occasionally I throw out the anchor at Crescent Beach and swim to the Sunset Beach Resort for a cocktail.
I believe the most romantic spot in all the Hamptons is a long walk down Ram Island Drive between Upper Beach and Lower Beach looking out at the historic Bug Lighthouse separating Gardiner's Bay from Orient Harbor. With no artificial lighting, the sky on clear nights is a star gazer's dream where you can see the Milky Way and even galaxies with the naked eye. I love experiencing the thrill of a shooting star there. I rarely walk there on a clear night and not see one. In September that "Harvest
Moon" rise is worth catching once in your life time from that spot.
If you haven't been on "The Rock" in the off season, it's really quiet, peaceful and provides a nice shelter from the craziness life throws at folks. I love the place, no man may be an island, but Shelter Island is the place for this man to go when he seeks some unique shelter and solace.