Around late January the holiday cheer begins to run thin. The harbor might be frozen over which means no boat. No boat!? Damn, I’m out of booze.

You’d think that by now a little planning would have been appropriate. Hell no. On the island, planning is just not part of the fun. In Dickie’s case, planning ahead wouldn’t matter and in fact could be fatal. Whether Dickie buys a bottle or a case, he just sits down and drinks it until it’s all gone. Five cases would be fatal and he knows it. Not to mention the loss of income thing, which isn’t high on the agenda, I know.

So now come the midnight raids on well-stocked summer houses, the other winter social event. The raids also provide a useful tempering device by adding a little bit of guilt to the mix. A few summer folks know about the raids but don’t have the heart to take the stuff when they leave for the winter. It’s cheaper than a caretaker. In fact there are no caretakers. The houses will be taken care of, never mind the muddy footprints. There is almost no worry that summer folks will show up before spring, as it’s pretty bleak in the winter and whatever niceness was displayed during the summer has been completely wiped away like theatre makeup.

The place is ours now, just the way we like it. “Leave your wallets and go home!” Bung has that sign in his basement but has never had the courage to bring it out. The boat ride at this time of year is scary at best. Worst-case scenario: taking the mail boat out to the island, having the wind come up and the boat stay over. We’ll put captain Ray up but you are on your own and camping; there is no mercy. We do have an island fail-safe for this situation. If somebody shows up at the boat who shouldn’t be showing up at the boat, Captain Ray calls the post office (the only trustworthy phone on the island) and Dottie gets the word out to whom it may concern. So if Bung is supposed to be working on Sally Smith’s house and Sally Smith shows up at the mail boat for a day trip, by god, Bung is going to be working on Sally Smith’s house. In fact, we may all be putting in the half day at Sally Smith’s until the boat hits the dock. We know he’s been sending her bills since September and we’ll all be looking to get bailed out in the spring. If there’s booze to be replaced quickly, the rob-Matthews-to-pay-Robbins rule is invoked.

At a certain point the ice doesn’t matter any more and the race is on to spring, a little more exciting than gazing across the steel gray frozen sound, dreaming of tropical bars, Bermuda shorts and bikinis. Last year Dickie slipped on the ice in his fuzzy slippers while trying to get up the hill to the Pierce house. Broke his ankle. The Coast Guard came and got him in the morning and he was back on-island the next day in a full cast. The Coasties wouldn’t take him to a liquor store so he took to night crawling right away, using his dog Mischief as a crutch.

This goes on all winter. The menu opens with the really fine whiskies and cognacs and by March or April it’s down to the fruit brandies. Once in a while a summer person will notice that, say, charter boat captain Willie Noise only drinks peach brandy as his summer refreshment, and we’ll agree that it’s a little odd. But we also know that he’s been drinking it since February and has just gotten used to it.

Now you may wonder why I have so much knowledge on the subject. There are two possibilities. One is that I’m right there in the thick of it, or — and you may not have thought of this — my mother might own a liquor store not far from the ferry landing and when spring pops around I am going to be a very popular guy. Both would be true. I wouldn’t be having any fun otherwise and besides it helps build trust if they’ve bumped into me a couple of times in the middle of the night with Beaujolais breath. We try not to bump into each other, but it’s inevitable, not much conversation, just a grunt will do, it’s all a bit embarrassing. There’s trouble in paradise.

Sometimes in March, a natural ruse will bring signs of an early spring and with it will come an insidious, creeping panic. In about two days the worrying will start. On day three when things start to bud out a little, work begins on houses. On day five the lists come out of all the booze taken over the winter. I reluctantly fill orders, knowing full well that in a few more days it’s going to turn cold and the raids will start all over again.

In a normal winter, without a freshet, the activity would taper off with the supply into mid-May and everything would calmly move back to normal. But now it’s a new year and the race is on again to empty every bottle by May.

Once in a spring conversation with Bill Pierce I asked how his house had fared through the winter. “Great!” he said. “And every one of my liquor bottles was full — but not a single brand that I drink.”

Will Monast and his wife Leslei live in West Tisbury. They washed ashore after spending 25 years on Cuttyhunk raising four children, but that’s another story.