Fork It: Let's Have A Weird Wine & Weed Weekend on Long Island
Ditching the basic beaches for ghosts, joints, and joyrides through Long Island’s weirdest corners
Hey everyone,
Can you believe it? I finally made it to the Hamptons, a place best known for high hedged gated communities and exorbitant wealth—two concepts that are both completely foreign to me as a human being, yet still in my wheelhouse as a service industry veteran journalist who’s stayed at a lot of really swanky luxury hotels? Life is weird! Does this make me “new money”?
Of all days to miss an anti-capitalist protest, I somehow picked No Kings Day to arrive—uninvited—at Ground Zero for the 1%. How gauche! I swear it wasn’t intentional! I just wanted a beach and some wine, maybe a little mini writer’s retreat and a break from this trash fire of a news cycle.
Should I be giving you the “Lifestyles of the Rich & Famous” version of this luxury-road-trip-on-a-budget tale or the “Everything you should do in the Hamptons that they don’t tell you about”? How about a little bit of both?
While I am the first to admit I am no Long Island expert (Teddy Minford wrote the sister companion to my Hudson Valley/Catskills guidebook on the Hamptons, Long Island, and Jersey Shore), I didn’t think it was fair to continue writing about our great state without giving it a little more attention and exploration—particularly to the finer parts often obscured from travel guides, including the weird, wild women and art freaks like Lee Krasner, Big Edie and Little Edie of Grey Gardens, and Julian Schnabel who added character to an otherwise unremarkable place—and the newcomers keeping things unexpectedly interesting.
For your skimming pleasure, this is segmented into three (!) parts:
The travelogue
The travel guide
Long Island beach reads
Enjoy!
PART I: The Travelogue
Love ‘em or hate ‘em, the Hamptons are exactly everything you’ve already known about them—and some of the things you might overlooked or forgotten about.
It’s true: this is a place where a $1.5 million property is considered quaint compared to its neighboring $39 million beachfront properties a few streets down—all of them quite boring from the outside and chronically under surveillance. Traffic is often impossible, but among the few where you’ll see people running errands in Bugattis and Maybachs. And it’s a place where money seems so irrelevant that people think they can get away with charging $14 for a latte. (Maybe trying to recover from that very public $200 million food hall flop?) Obviously, I had to see it for myself.
(Speaking of, if that $14 latte is where Zohran got the $30/hr minimum wage number, it certainly illustrates the disconnect).
But let’s be real: oligarch spotting was not why I was in the Hamptons. The trip was entirely self-motivated: I wanted to go on a writer’s retreat (without having to pay for one). Somewhere coastal but not international, regional without getting on a plane; a quiet backdrop perfect for a Mary Higgins Clark writing fantasy. While I was there, maybe I’d take in some art and the ocean, have some good eats, check out some of Long Island’s wine offerings, see if I wanted to make a whole summer of it, y’know.
Coastal writing retreats are a pretty standard benchmark of imagined writerly success if you grew up watching episodes of “Murder, She Wrote”—ending up in weird places like a curious outsider unafraid to chase a good story. I wanted to try it on for size.
As someone who is not originally from New York but written about it a time or thrice, I’ve always considered myself Long Island agnostic and openly ignorant. Everyone seems to have an opinion about this place, but I was there for the wining and dining with very little interest in ruining a meal by learning how the sausage was made. Between the current chaotic evil political climate and environmental one, I didn’t expect an easy weekend getaway, but decided to try anyway. Could my polite Midwesternisms carry me to a completely stress-free Hamptons weekend?
The Hamptons have the psychic vibe of Stepford Wives meets The Truman Show meets a bafflingly normative American suburban town, but with bajillionaires and weird empty real estate being used for influencer parties or being demolished in favor of new construction. It’s a little soulless, even though it has so much history—even if that history has always been historically inaccessible. I don’t know how much of that is changing, but then again, technically everywhere is changing.
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There’s a bizarre sense of deja vu here and the subtle reminders of being an outsider. If you have no business in the Hamptons, you’ll be the first to know without anyone even needing to say anything. For everyone else, it’s just, like, their normal town. I can see how people who live there might not even recognize any of this as abnormal because this is just day-to-day being surrounded by people who look and act like them—and explains why I felt so thrown off seeing a Home Goods store wedged between plastic surgeons and luxury patio furniture retailers.
It all just felt so unassuming amid this backdrop of multi-million-dollar countryside mansions and remarkable in how completely unremarkable it is. Aside from the absurd real estate prices, there’s nothing that differentiates this place from Anywhere, U.S.A. except the appeal of coastal proximity and its elite cultural legacy.
To the rest of the world, the Hamptons are where rich and glamorous New Yorkers go to feel unbothered—along with the people who admire them and want feel unbothered and glamorous, too. But it’s also filled with the sea and tribal people who were already there, plus all the curated aspects of community and culture afforded to those who can afford it. Plus, all those ghosts (the other reason I was there).
Because this part of Long Island is so impossibly expensive and intentionally challenging to navigate by design, most of my previous experiences have been limited to day trips—a day in Montauk here; a day in Fire Island there; an afternoon in Long Beach, eating sandwiches over a sunset in Port Washington; zipping around to the quirky goth coffee shop and record stores near West Hempstead.
Over the past few years, I’ve developed an affinity for day trips in the North Fork, particularly to Greenport for scenic tastings at the Kontakosta Winery followed by a rocky dip at 67 Steps Beach, strolls along the boutiques on Main Road, grabbing a lobster roll and trying to catch Matchbook Distilling during the handful of hours they are actually open, then watching the sunset over an ice cream cone before heading home. It’s a great afternoon that doesn’t require a $400/night hotel room—but does require some real dedication to organization. If you can pull it off, it’s very charming.
Like many New York towns that fell into disrepair or were known affectionally as a “shithole,” recent years have seen redevelopment efforts in the North Fork and elsewhere that resulted in much nicer cities with the price tag that reflects it. In some ways, that makes for interesting conversation with multi-generational locals who have witnessed these changes and now sit somewhere between the other side of the tracks and where the grass is greener, with no place to go and no reason to move. For everyone else, it’s a scenic little getaway.
Each time I’d take the train or Jitney, bypassing the wine region that is nearly impossible to visit without a pre-arranged driver and itinerary (Ubers are getting better, but still spotty depending on where you’re at). Without friends with mansions and at an age where even a coffee date requires three calendar polls, the South Fork mainly remained a mystery. Every time I got close, logistics pulled me back.
Now that we’re in a legal New York, that cannabis scene is slowly making its mark in the Hamptons thanks to forward-thinking brands like House of Puff and Little Beach Harvest, a local tribal-owned dispensary with its own outdoor consumption lounge and sprawling event space setting the pace for the rest of the state to follow (not to mention killer products and an overall incredibly impressive design—truly wish I had more time to have kicked it there because that in itself is a destination).
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I was surprised and delighted to find reasonable accommodations in Southampton at AirBnB and just enough points on my credit card to cover the cost of a rental car. The caveat, of course, was getting exactly what I paid for: an uncomfortable room in a weird, extremely dated suburban home, and unseasonably cold for June. Somehow, no matter where you stay, all of the options feel like you’re getting a little ripped off.
The weather was not cooperating and the idea of co-habiting with a mail order bride and her family did not sound particularly enticing for a vacation, so I found the creative inspiration to find other shit to do. This is how I ended up on an unintentional pastry crawl, a quick stop exploring Sag Harbor, a last-minute addition to the Pollack-Krasner House tour, and a drive-by at Grey Gardens, the unofficial historical landmark for wealthy eccentrics cemented in the iconic eponymous documentary, movie, play, and countless inspirations.
Throughout the weekend, I found myself sneaking off to hit joints along the remote stretches of beach where there wasn’t another person in sight. There’s something kind of romantic and dramatic about the unobstructed experience of having the ocean roar at you while the wind whips you around a little bit (something I chalk up to being a Pisces from South Florida).
On one hand, this was incredibly liberating—I go to the beach to be alone, but also to be in love. (In fact, it’s the inscription of my book: “For those who want to fall in love between where the sky meets the earth.” Pretty simple stuff—just let people have their sunsets and fall in love, y’know? Even if it’s with themselves). On the other hand, I’ve watched a lot of Lifetime biopics and I wasn’t particularly interested in becoming another tragic ripped from the headlines.
I’m pretty sure I was trespassing on most of the beaches I ended up on, but no one was there anyway. You’ll never see a car parked on a street outside miles of gated properties—but you will see plenty of cameras and the occasional cop hiding on a side street.
Ultimately, I learned that the Hamptons are not for me (or least as long as I’m not paying). Even as an outsider, I wanted to believe there was still a place at the edge of all this wealth to write, wander, and fall in love quietly. And there is—just maybe not here. But here are my recs for an easy wine and weed fueled weekend in the North Fork and South Fork of Long Island anyway.
PART II: The Travel Guide
FRIDAY
12 p.m. - Get out of dodge. Even if you leave New York City by noon, you’ll still end up in the most hateful Friday afternoon traffic. Arrive in Southhampton by 4.
4 p.m. - Visit Wolffer Estate for a tasting. There are only three wineries along the South Fork, but Wolffer stands out among the most recognizable in Long Island wine. Best known for its rose and cider, the Sagaponack tasting room offers sweeping views of the 55-acre vineyard, making it a popular spot for girls weekends and special occasions. Around the corner, Wolffer has an outdoor Wine Stand that hosts seasonal sunset music series and morning yoga sessions (no reservations required). Fun fact: Rihanna and A$AP Rocky both have signed barrels here! And they have a pretty solid non-alcoholic wine for the NA folks!
6 p.m. - Have dinner at Shippy’s. Before I left, I was informed that the Hamptons style du jour is a Brandy Melville-inspired crochet sweater with American flag across the chest. This was exactly the first thing I saw as I walked into this restaurant—an elevated classic New American tavern and Southampton mainstay for over 50 years. So, that’s the vibe. I ordered a shrimp cocktail and Coopers Beach fried fish sandwich as I mentally checked out for awhile.
8 p.m. - Walk in circles for two blocks. The main strip of Southampton is populated with familiar outposts of New York City restaurants, luxury real estate offices, and designer boutiques that look like Charleston and Chapel Hill. If you’re lucky, no one will be hanging around Agawam Park, which offers a serene waterfront view stretching towards Gin Beach, illuminated only by the light of the moon and stately columns backing the World War I Memorial, before heading back like a teenager trying not to get caught.
SATURDAY
9 a.m. - Grab breakfast at Armin and Judy. This was among the best meals I’ve had in a while. If I had to choose one restaurant worth going out of my way from this entire weekend, I would say it’s this one. I spent maybe $35 on pastries at their bakery, but would have spent more. The Aneri espresso offered a rare perfect cup of black coffee paired with the most buttery, flakiest croissant and gravlax latke waffles backed by jazz renditions of pop songs and rain beating against the window. Can’t say enough good things about this place.
11 a.m. - Pop in for a tasting at Duck Walk Vineyards. This is a pretty accessible winery for people with limited knowledge of wine and few questions beyond “Can I get a top off?” But as a wine geek, I thought their Pinot Meunier was a real sleeper hit, using 100% Pinot Meunier as a light red—particularly since most people’s familiarity is being among the three main varietals used in Champagne production.
12:30 p.m. - Go on an adventure. Originally, I planned to hit up the Lobster Roll in Southampton followed by a tasting at Channing Daughters in Bridgehampton. But the tasting room was outside and the weather was freezing and raining, so I decided to pass. While the Parrish Museum is right next to Duck Walk (with a pretty incredible collection), I ended up taking a detour to Sag Harbor where I continued my unintentional pastry crawl at Carissa’s (the pistachio croissant had too much stuff, but otherwise exceptional), browsing the titles at Sag Harbor Books (mint condition used books with an interesting metaphysical and poetry collection), popped into Provisions food store (that looks like most of the fancy bodegas in Brooklyn), and Schiavoni’s, a historic grocer (where they sell $12 green juices in the same plastic bottles as the Nutcrackers sold in the Rockaways).
2 p.m. - Visit the Pollock-Krasner House. If you want to do this, you need to make a reservation. Only 12 visitors at a time are allowed on the tour at the former home of iconic artists Jackson Pollock and Lee Krasner now endowed to SUNY. Not only is the tour fascinating and intimate, but the house features a rotating gallery exhibition where the works of Rosalyn Drexler are now on display and the gift shop is worth dropping a few bucks. I also think it’s a nice touch that you can purchase a clipping from Lee’s spider plant, which has been living well-beyond her death in 1984.
3:30 p.m. - Check out Amagansett. Or rather, Amagansett Square, a tiny strip of shops and restaurants where you’ll likely do more window shopping than credit card swiping (unless you have a very high credit line). For the sake of it being there, I did stop into The Row, where even without looking at the price tag there was nothing I wanted to buy, and spritzed myself with a little D.S. & Durga at Love Adorned. That said, I wanted to buy the whole store at Cavaniola’s Gourmet, a well-known cheese and chocolate shop filled with local and international delicacies, and Doubles, a sunny Caribbean-influenced casual spot for roti, doubles, ice cold beers, and Van Leeuwen Ice Cream. Vinyl hoarders should definitely check out Innersleeve Records, where they have a pretty good stockpile of Record Store Day leftovers and rare pressings.
4:30 p.m. - Make a pilgrimage to Grey Gardens. I have a bit of a kindred connection with this place because Big Edie and Little Edie remind me a lot of my grandmother and mother (without all the familial financial padding and squalor). To everyone else, they are fascinating eccentrics and subtle countercultural icons against their buttoned-up neighbors. Today, the mansion is obviously in much better shape and now under the ownership of fashion designer Liz Lange of Figue and Liz Langue Maternity for Target, but that didn’t stop me from rolling up to take a quick car selfie outside, followed by driving around the empty tree-lined streets of East Hampton.
5:45 p.m. - Slip into Dia Bridgehampton before they close. Unless you’re planning on some deep meditation, you probably won’t need more than 30 minutes max to see the Dan Flavin permanent installation at Dia Bridgehampton—where the admission is always free and the selfies are always on point.
7 p.m. - Treat yourself to a lobster roll and slice of key lime pie at LUNCH Lobster Roll. Housed in a former diner, there’s something charmingly Americana about this lobster roll joint where the food is exactly what you’d want and expect from a Hamptons institution.
SUNDAY
8 a.m. - Visit Tate’s Bake Shop. Drop more money on baked goods, only to realize that there is nothing particularly life-changing about the bakery (but still very good).
9 a.m. - Get high at the beach and write in your car for an hour and half. I’m pretty sure I was trespassing, but did it anyway. Oceanside writer’s retreat officially ticked off the bucket list.
11 a.m. - Visit Little Beach Harvest Dispensary. It’s about a 40-minute drive to this tribal dispensary owned and operated by the Shinnecock Nation—among the few Native Peoples still living on portions of its ancestral lands. Because of their autonomy, it’s also one of the only legal consumption lounges in New York State, with next-level design that I think others in the industry could really take a lesson from. More so, you can buy tribal weed here, which is locally grown and fantastic, while supporting small indigenous businesses and community.
12 p.m. - Swing by any one of the million farm stands to pick up fresh strawberries. I actually can’t remember which one I stopped by but it doesn’t matter because there are so many and they’re all super fresh and better than what you can get in the city.
12:30 p.m. - Do a tasting at Chronicle Wines. There were a lot of North Fork wineries to choose from, but I was particularly jazzed about this up-and-coming woman-owned winery from Robin Epperson-McCarthy and Alie Shaper who are really bringing some unique personality to their wine-making styles and redefining the North Fork flavor. Each winemaker has their own labels under the Chronicle umbrella that reflect their individual approaches and the tasting room is cozy and intimate in a way that feels like being in someone’s home. This is another place I would go out of my way for—and if you’re really into wine, you might find yourself wanting to stay there all afternoon talking shop.
1:30 p.m. - Have lunch at 8 Hands Farm. This is not a cheap lunch, but it’s also one that you won’t feel like pinching pennies over because the quality here is next-level. I ended up buying a container of pickled eggs after having their salad made with fresh greens, asparagus, radishes, pickled eggs and a yogurt-based green goddess dressing that made me wonder why no one can still get salads right ever.
2:30 pm - Send yourself off with a tasting at Sparkling Pointe. If you like your wine as bubbly as your personality, make time for a stop-off at this 40-acre estate known for producing sustainably harvested sparkling wines exclusively in the traditional Méthode Champenoise.
PART III: Long Island Beach Reads
Inspire your own uninvited mini writer’s retreat with these beach reads:
Long Island Compromise by Taffy Brodesser-Akner
Ninth Street Women by Mary Gabriel
The Guest by Emma Cline
Sag Harbor by Colson Whitehead
The Great Gatsby by F. Scott Fitzgerald
The Power Broker: Robert Moses and the Fall of New York by Robert Caro