My First Tumbleweed Tuesday

Yesterday was my first Tumbleweed Tuesday, an annual holiday on Shelter Island, far out near the eastern tip of Long Island. Businesses close for at least a day, and locals, many of whom work two jobs in tourism throughout the summer, get their island back.

Shelter Island is only 29 square miles, a tad smaller than the island at the opposite end of Long Island, Manhattan, but has just 2,000 year-round residents. That balloons in summer to many thousands more, with all the people with summer houses, along with tourists and day trippers.

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Tumbleweed Tuesday.

I came here around 4th of July to manage the dining room at an historic hotel called The Chequit. I’ve been a waiter for many years, and looking for the right time to make a move to management, and jumped in here with the tourist season already underway. (Hence the long silence here on More Has To Happen.)

Having spent just a night on the island back in late June when my wife and I came to look the job over, I knew I was entering a place with a unique social landscape, shall we say. Because the restaurant I was managing was historically a beloved dive bar that went upscale a few years ago, when the hotel above it was bought and renovated, I was on the receiving end of lots of advice from “locals” about how I should run things.

I say “locals” because that means many things to many people. Every day middle-aged guys came to me and gushed about how great The Chequit’s bar was in the 1980s when they had their first underage drink there. The fact that they’d stopped going there twenty years ago rarely softened their firm belief that it should stay exactly as they remembered it. I suppose if I went back to New Brunswick, New Jersey, where I went to college, and found an osteria where Patty’s Pizza used to be, I’d feel a little heartbroken too, but I wouldn’t go inside and tell the manager about it.

When dealing with locals, I learned to discriminate between the true local and the person who tells you that they’re a local a little too freely.

I think I made some lifelong friends this summer. Shelter Islanders like to say, “It’s becoming like the Hamptons,” meaning it’s seeing more of the Wall Street money that took East Hampton and the sleepy towns around it and turned them into a summer-long eugenics experiment for the wealthy. When a true Islander tells me he’s sad to see people like me selling $100 bottles of wine, I tell him a., I wish I’d sold more of them, I can’t get these people to spend enough; and b., he’s right.

All was forgiven on Tumbleweed Tuesday though. Salt, one of the competing restaurants, hosted a party on Crescent Beach, and lots of restaurant workers who’d come out from the city to make some cash over the summer were drunk as sailors. Summer parking rules were no longer in effect, and lots of pickup trucks lined the road. I saw off duty law enforcement officers sipping beers with their extended families. I took a long swim, past the buoys, and indulged a little myself.

There is pressure, but also comfort, in working for a place with so much history. You get the sense that even if you mess up your job completely, people will still come back next year. The days will get shorter, then longer again, and someone will do your job, and make some slightly different decisions, but fish will get fried, and money will get made, and those remaining will sit on the beach the first Tuesday in September and say that the water is still pretty warm.

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Crescent Beach, Shelter Island, September 5th, 2017.

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