Chris Fenimore's Guide to the North Fork of Long Island

Chris Fenimore is a friend, a talented photographer and writer, perhaps most well-known in the menswear scene on account of his long-running ‘Five Fits With’ series for Esquire. (He also featured my wife, one of two women to appear in the series before it ended.)

Recently, Chris relaunched something similar for GQ, called Real-Life Wardrobe, with a cool, expansive scope of guests talking about clothes (and life) - from Earl Sweatshirt to Brunello Cucinelli.

I am particularly excited to share Chris’ guide to the North Fork of Long Island, where he lives, because it’s a place I’ve been meaning to visit for the last several years. I’ve known Chris to have great taste, especially when it comes to food and wine, and trust that his recommendations are very much in line with what we do here at A Small & Simple Thing. This is a great guide, and has me looking to book a visit soon.

If you like what you see, you can follow Chris on Instagram or subscribe to his newsletter.

And now, let’s hear from Chris:

As of this spring, I’ve lived on the North Fork of Long Island for 6 years. I’m from Brooklyn originally—the kind of New Yorker who assumed they would rent within the five boroughs till they die. I met my wife, Lindsey, a native North Forker, at a sweltering June wedding in 2018 and we were soon inseparable, save for the 90 miles between us.

Sometimes, she would drive to Brooklyn for dates. Or, I’d borrow a car or take a Hampton Jitney east to see her. I’d usually meet her on a Saturday evening at the vineyard where she was working, Lieb. While I waited for her shift to end, I’d watch the sun set over the vines with a glass of sparkling Pinot Blanc in hand. I wasn’t in Bensonhurst anymore, Toto.

This is when my relationship with the North Fork began. At the time, Lindsey was living in a one-bedroom bungalow, 100 feet from her grandmother’s house, on a private beach on the Southold Bay. I grew up going to a very littered, very crowded, and very loud Coney Island. It was an experience I cherish, but I quickly came to prefer this flavor of beaching. When the pandemic started, she convinced me to break my lease and move in with her and my stepdaughter.

We had a beautiful, pristine beach to walk on daily, and in the other direction, tranquil woods. I had never considered these luxuries as possibilities for myself. I had also never experienced fresh local produce, something so abundant and available here during most seasons.

I missed my friends and the things that make New York City so alluring—and still do—but I also came to see the benefits of living on the North Fork, especially during the warmer months. Life became easier once I stopped comparing the two. I’m still learning how to live here in the winter, when some of our favorite restaurants shut down most days, the farmstands close for the season, and the typically lush landscape turns lean.

Toward the end of 2021, before we got married, we bought a house in Cutchogue, where we live today with our two children. We are sandwiched between two of my favorite farms within a mile to the east and west. We walk our daughter to and from her fantastic public elementary school just three minutes away on foot. Today, I consider myself a North Forker. There are a host of gems that I love out here. Without getting carried away, here are some of my favorites, starting east in Greenport and working our way back west.

Bruce and Son – This is my favorite restaurant on the North Fork, but it’s also one of my favorite restaurants, full stop. Everything on the menu is healthy, local, and seasonal, rotating every month or two. The egg sandwich, also one of the best I’ve ever had, is always on the menu—a folded omelet with melty gruyere, sugared bacon, pickled onions, arugula, and dijonnaise - all on a brioche bun. I’ve been ordering their carrot “lox” sandwich these days. Chef Bollman smokes thinly shaved carrot to resemble salmon. It is mind-blowing and delicious. The restaurant is on Greenport’s lively Main Street, so you can walk your meal off once you’re done.

Brix & Rye/1943 Pizza Bar – This speakeasy-style cocktail bar is a Greenport staple. I’ve had countless dates here with my wife. This place is special to me, and everyone who works here, from the owner to the host, have become friends. They also serve perfect brick-oven pizza from 1943 Pizza Bar. I highly recommend the restaurant, too, which is upstairs, but we much prefer to eat in the romantic, dimly lit bar below. The night before our wedding, we had their pizza truck parked in our driveway. Matt, the owner, was cranking out beautiful (and necessary) pie variations all night.

The Halyard – Located in Greenport at the iconic Sound View, a waterfront hotel built off of the Long Island Sound, this is one of the North Fork’s fancier restaurants, though the setting is still relaxed. Book a table around sunset, and you’ll understand why everything costs a bit more here. The food and drinks are fantastic, so you’re getting what you pay for.

Little Creek Oyster Farm and Market – Do you like beer? And oysters? And fancy hot dogs? This is a completely unpretentious experience in a unique space in Greenport, with an interesting food menu, and many variations of grilled and raw oysters to enjoy with local beers and wines. They’ve got a full bar. If you’re on vacation, the siren song of the Painkiller might call to you as it has to me on many a hot summer afternoon.

Beall & Bell – My wife and I have purchased several large furniture pieces from this renowned antique shop, including our dining table and a large hutch for our kitchen. It’s on Main Street in Greenport, and they’ve got hundreds of items in an expansive, idiosyncratic space—even things as small as desk tchotchkes and oil paintings, so you can bring them back with you in your bag.

One Kourt Studio – This is one of the best wine shops, not just on the North Fork, but anywhere, focusing on interesting, passionate producers who often deal in small batches. Tyler, the owner and proprietor, prioritizes sustainable, organic, and biodynamic practices. He has a host of price points, styles of wine, and regions represented. He’s also got a great array of interesting liqueurs—vermouth, amaro, chartreuse, rum—you name it. He’s always ready to answer your questions, show you his new favorites, or just shoot the shit.