Sixty-Something: Unique Shelter Island Stands Alone

Every summer, I make a few visits to Shelter Island – both by sailing there and by taking the South Ferry or North Ferry with my car. Part of my first full-time, paying job in the Hamptons was delivering a weekly free magazine to Shelter Island once a week for almost four years. A magazine that had my articles. I still remember that snowy February Friday morning I was the only vehicle on the South Ferry both coming and going. Driving between the coldest, whipping wind, forming ice everywhere and the wicked snowy roads conditions was an adventure. Yet, the memory of that whole day is my favorite. You see at almost every drop off location during that storm was someone who said, “Good morning.” With many offering coffee. Yes, everywhere looks new and different with a foot of snow.

However, my last two visits to Shelter Island was this week. One by sailboat and one by car, both on 80-plus weather days with fantastic soothing sea breezes. You see there is something special about a small Island only accessible by ferry or some other kind of boat.

Many say Montauk is the “Unhamptons.” Well, Shelter Island is something much more because it is pure Americana. It is as if Norman Rockwell designed every home, building, and inn – because everywhere you look you see majestic historical homes that give you the feeling you have both gone back in time and are visiting somewhere with a huge soul. It is true that Shelter Island has been a summer vacation home Mecca for over a hundred years, and in August on weekends it gets “busy,” but that ferry acts as a gatekeeper to screen out annoying folks and people who don’t like to be inconvenienced. It is a place for quiet serene moments and for extremely high quality time with families, or even by oneself. For the locals, it is so much more – it is their home, to protect, and safeguard.

Although many hot spots were still maneuvering to adhere to the ever changing safety protocols to prevent the Coronavirus, it was tragic to drive down to Crescent Beach, known to many as Sunset Beach, on a hot, sunny August Sunday and see the Sunset Inn boarded up. I have had so many wonderful experiences there over the last thirty years that seeing it boarded up like a condemned property was sad. I am sure it will be back next summer serving wonderful international meals and mixing up some of the best mojitos on earth.

The author with his Marie Eiffel Market lobster roll. (Courtesy Photo)

However, open for business was Marie Eiffel Market. I believe at this venue the best lobster roll on the East End is prepared and sold on a very tasty very French “brioche.” Of course I sampled one.

Dering Harbor is a post card view in every direction, every day of the year. Sailing into Dering to tie up at the town dock is a ritual I have now done a few times every summer for seventeen years. This last weekend, the harbor was buzzing with multiple size sailboats and power boats, along with a few kayakers and paddle board enthusiasts. In every direction you look, you see beautiful boats. However, that February snowy day, only a single commercial fishing boat was in that whole harbor.

Last week, I achieved a first. I literally sailed without motor from my Three Mile Harbor slip to the Shelter Island Rams Head Inn dock at the end of Coecles Harbor never using my motor! Coecles Harbor has an entry of about twenty yards wide at high tide and other than dead center past the green buoy, it can be only a foot deep. To sail in safely, you need the right wind, the right tide, and a lot of nerve. Coecles Harbor, Shelter Island is a favorite day trip or overnight destination for many boaters.

Lastly, I cannot write about Shelter Island without mentioning I love small car ferries! I love standing amongst the cars feeling the boat vibrate from the powerful engine that fights all winds, all currents and all weather dozens of times every day all year round. When it leaves the dock, I become but a boy enjoying the short ride to a magical place.