Sheltered Islander: 7 Simple Rules for Shelter Island Living

Sean Connery on Shelter Island
Sean Connery on Shelter Island, Photo: Clive Brunskill/Getty Images Entertainment/Thinkstock, Oliver Peterson

Nothing stays the same, does it? I remember when nobody knew where Shelter Island was, not even people in Southold. All the housing was affordable because nobody wanted to live on an island. It was just families who worked here, and our population of “artsy people.”

There was an incident once when Frank Sinatra wanted two locals to move their boats because his boat needed three spaces. He yelled, “I’m Frank Sinatra, move your boats.” The response, “Not here you ain’t. You’re just a tourist, you move YOUR boat.”

Celebrities are not uncommon here. But locals never bother them. It’s just one of our rules. About 15 years ago I saw Sean Connery waiting in line at the pharmacy. One of the items in his basket was Advil. I maintained my cool until I got back to the car, then I cried—007 can’t need Advil, he just can’t…

Nobody knew about the Island until the Clintons said they were thinking of moving here. All anybody could think of was, the Secret Service will commandeer the ferry every time they want to go somewhere. Then East Hampton, with malicious aforethought, put a moratorium on building new houses. So they sent buyers here. It was all part of their plan to turn us into North Hampton, or worse, Hampton Island. We know a hostile takeover when we see it.

Many of you won’t like it here. But if you wanna live here, we have rules.

1. No small, yippy dogs. Dogs must be Labradors, or similar breeds. No dogs with dyed fur. If you have a pink poodle, you can’t live here.

2. Your house must be painted an approved color—grey, nautical blue, ocean green or white. You may choose any shade of black or white for the trim and shutters.

3. Bring two cinder blocks and a ball of twine. Place the cinder blocks on your garbage cans each night. Tie the twine to a cinderblock, weave it through the house and tie the
end to your big toe in bed. This is your raccoon alarm. The rest will be self-explanatory.

4. We have many farm stands that work on the honor system. Once, when I was short on cash, I left an IOU with all my info at Kilbs farm stand. I was going to leave one of my children as collateral, but I didn’t have enough rope in the car that day.

5. When interacting with any Island merchant, please remember, we don’t give a rat’s ass how they do it in the city. Don’t even ask.

6. Don’t drive expensive cars here. The seagulls are diabolical. I once saw a pretty little red car parked between two Island trucks. There was a big dent on the hood with broken clamshells surrounded by seagull poop, all drying in the sun.

7. If you’re a celebrity, check your ego on the ferry. If 007 had to stand in line, what chance could you have?

Lastly, we don’t want to be “Hamptonized.” This island is for families, not the nouveau riche. We are building a Maginot Line of cannon right now aimed at East Hampton. We have thousands of rubber chickens stuffed with fish guts, and we’re not afraid to use them. So you just reconsider that building moratorium!

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