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This Holiday Weekend, Plan Your Staycation at These Restaurants and Wineries

All the fun with none of the travel.

Looking for a low-key getaway? This fall, instead of hopping on the nearest plane, consider the glories of your very own backyard. The art of the staycation is often overlooked by travelers, but with a host of excellent dining establishments and wineries right here, there’s no reason to deal with the airport. Read on for our favorite picks for a North Fork staycation. 

Southold General

Southold General

Michelin-starred chef John Fraser has opened his newest North Fork project, Southold General, a one-stop-shop for local produce, excellent coffee, gelato, and even pizza. Like general stores of the past, Southold General is part market, part café, with made-to-order salads, pastries, and homemade focaccia. Fraser has partnered with French pastry chef François Payard, guaranteeing top-notch sweets and baked goods. An online ordering portal allows guests to order seven superlative pizzas online — but a visit to this curated shop is a must for your next North Fork staycation.

McCall Wines

McCall’s recently renovated tasting room is pleasure to spend time in. Reservations are accepted online for any of the winery’s bespoke tastings, available on outdoor picnic benches overlooking the vines. Walk-ins, however, are also available on a first come, first served basis. In addition to wine, McCall serves artisanal cheeses and charcuterie and, on Thursday and Friday evenings, they host a burger night, with burgers made from their own Charolais beef (reservations required for burger night). 

Bruce & Son

The art of brunch is alive and well in Greenport, where you can get this in-between meal all day from Thursday through Monday. Seasonal produce dictates Bruce & Son’s broad menu, where you may find an heirloom tomato sandwich on brioche with za’atar mayo; a beetroot toast with pickled green tomatoes and labneh; or even a hotcake served with New York State maple syrup, grass-fed butter, mixed berries, and seeds. The restaurant’s ambitious drink list — boasting both alcoholic and non-alcoholic libations — is reason enough to dip in. Where else on the East End will you find Vietnamese egg coffee, a delicacy served in Hanoi that turns morning coffee into airy morning custard?

Sparkling Pointe

Celebrate your staycation with bubbles — and lots of them. At Southold’s Sparkling Pointe, traditional method sparkling wine is the name of the game. Reservations are required for the winery’s 90-minute tasting experience, a seated experience in which guest can choose from flights of wine, chocolate pairings, caviar service, and even distilled spirits. Eleven sparkling wines are available by the glass, for those looking to experiment with style, color, and flavor profile. Take home a memento from the day with a $10 Sparkling Pointe flute, perfect for the bottle you buy for later. 

Sparkling Pointe


At Greenport’s Gallery Hotel, get whisked away to a tropical island at Kon-Tiki, an island-y respite from our own island. The pan-Asian-inspired menu features everything from tuna poke with mango, cilantro, and crispy wonton to pork soup dumplings with Thai chilies and scallion. No Tiki-themed establishment would be complete without a well-rounded roster of drinks. Truly transport yourself with the Thai Me Up: Mai Tai-style Agricultural rum, orgeat syrup, pineapple juice, and lime. Vacation starts at home, after all.