Off-season fun in Montauk

At the very end of Long Island you’ll find Montauk, the end of the line on the Long Island Rail Road; the train station might be familiar if you’re a fan of Eternal Sunshine of the Spotless Mind. In recent years, Montauk’s popularity has boomed, becoming an extension of the Hamptons in the summer. But in the off-season, it remains a secluded and mysterious town.

I have come here every year for the last five years — Montauk is famed for its incredible striped bass and largely untouched natural beauty. It’s affectionately known as a drinking town with a fishing problem, and that’s what we found: we planned to fish Monday to Saturday, but with bad weather setting in, the fishing was over by Tuesday and with the rest of the week looking impossible for getting out on the water, we had our fishing problem.

In the mornings we would leave at 6 a.m., stop at a deli for a bacon, egg and cheese bagel, a two-pint vat of coffee blended exquisitely with Cinnabon creamer, and a variety of colorful isotonic sports beverages to fortify us for a day on the water. Even when there was no fishing to be done, I found myself walking down the highway in the morning to embrace this fine breakfast tradition so hard to find outside America.

The walk into town from my motel was about three miles down a maze of avenues surrounded by thick woodland. Transportation here is almost entirely by car, and it’s both exciting and perhaps unwise to walk — but Citi Bike has yet to expand to this neighborhood and I was stuck.

Rows of immaculate gated mansions (the landscaping business here must be booming) sit alongside smaller, sometimes completely dilapidated cottages. The odd house is adorned with MAGA flags, turning the tranquility of this quaint setting into a sudden unease that I could just disappear and no one would ever find me.

The town itself is situated around a large roundabout, or “Carl Fisher Plaza.” Fisher was a brilliant entrepreneur who developed Miami Beach and the Indianapolis Speedway, then tried to repeat his success by building the “Miami of the North” here in Montauk. But the project collapsed during the 1929 financial crash, leaving the town largely a fishing destination until the 1960s, when the likes of Andy Warhol, the Rolling Stones and a small surfing community exploded. Now Montauk has many tourist shops selling all manner of beach equipment, a bespoke vape shop, naturally, and several nice coffee houses.

Thinking I might get a book or some sort of weekly British political and cultural news to fill my day, I went to the town bookstore and to my surprise, next to Matthew McConaughey’s Greenlights, was Tom Baldwin’s recent Keir Starmer biography. I suppose I got my hopes up a bit too high on the strength of this: when I rang local bars to find out about seeing the Anthony Joshua-Daniel Dubois fight, none of the proprietors had a clue what I was talking about.

Historically, most Montauk restaurants — with or without pay-per-view boxing — close up after Labor Day, marking the end of the busy summer season when Montauk’s population goes from about 4,000 year-round residents to roughly 30,000.

Luckily for us late-September visitors, despite our fishing problem it was still a drinking town. There were still a great number of places to drink, and eventually eat at, like the Dock, with its dark wooden interior, its walls and ceilings covered in Americana. Phones were once firmly banned here, and you would be berated via megaphone for using one. Now it seems they are merely frowned upon, as I watched the next table over making sure to capture the entirety of their dining experience. I had — but respectfully did not photograph — the Clams Casino, grilled clams covered with breadcrumbs, bacon and tabasco.

Marlena’s Pack Out is another great bar, a single-room bar on the edge of a marina — the kind of place where you open the door, everyone turns around, realizes they do not know you and you’re an out-of-towner, and immediately turns back around. The excellent yacht rock hits I put on the jukebox were politely turned down from behind the bar; I had clearly misjudged the appetite for Steely Dan.

A great place to watch a sunset and sign off on another day of excellent work was the Montauket. Not only does it have a very fine beer garden, here there seemed to be a unanimous appreciation of the musical stylings of Steely Dan and Tom Petty. Sunsets in Montauk are really so spectacular that almost everything looks great, including the parking lots.

Another excellent local attraction is the Montauk Brewing Company, which has grown to enormous success from its origins as a small beer garden. It offers several delicious and deceptively strong IPAs in plastic cups; the Montauk Wave Chaser is as delicious as it sounds.

When locals can be coaxed into actually speaking to you, you get incredible stories about the area. Along with a story about a wedding his family had been to in Newcastle, I was told by a fishing guide that I might enjoy reading about the abandoned Camp Hero radar tower. This led me to the “Montauk Project conspiracy,” a local legend involving parapsychology, repressed memories and alien abduction, which formed a large part of the premise of the Netflix show Stranger Things. When I looked it up Reddit took me straight to missing people, UFOs, time travel and experiments in psychological warfare, but it turns out you can just go and have a look at the Radar Tower.

Near the iconic lighthouse, whose museum I bypassed on my pressing quest, I followed a few winding dirt roads, occasionally passing ominous signs of military activity. Eventually I was led on tarmac paths to an enormous concrete structure surrounded by a large chain-link fence, which suddenly seemed like exactly the sort of place clandestine government operations would have occurred.

The legend of Frank Mundus is somewhat more historically verifiable: a local shark hunter, Mundus became the basis for the Quint character in Jaws. Mundus, who was said to paint his big toenails red and green to be sure of port and starboard, was a charter captain who found that there were more sharks than bluefish in the area, and adjusted his plans accordingly. A nearby marina displays a replica of one of his whoppers, a 3,427-pound Great White shark, which he caught with rod and reel for a world record that still stands.

Montauk has changed during the summer months, but in the off-season, it’s still the same special, strange and beautiful place it’s always been. I hope it stays that way — a great place to not go fishing.

This article was originally published in The Spectator’s January 2025 World edition.