Best Long Island Wineries to Visit

Kontokosta Winery sits on a 16-acre bluff above Long Island Sound, one of fewer than a dozen North Fork vineyards with direct water views. The estate produces small-lot wines from estate-grown Cabernet Franc, Merlot, and Chardonnay, fermented on-site in a gravity-flow cellar built into the hillside. The tasting room opened in 2014 and has since become a weekend anchor for visitors touring the Greenport wine trail. The best long island wineries to visit share a few traits: transparent tasting fees, real vineyard acreage, and a format that respects both serious tasters and casual drinkers. Kontokosta checks all three. There is no cover charge to enter the property, and you pay only for what you drink—a structure that keeps the experience flexible whether you want a single glass on the lawn or a seated flight comparing vintages. The outdoor terrace holds around 60 guests, and on summer weekends it fills by mid-afternoon. Arriving early means claiming a table with unobstructed views across the Sound toward Connecticut. Long Island's wine country spans roughly 30 miles from Aquebogue to Orient Point, with more than 60 licensed wineries clustered along Route 25 and the parallel back roads. Kontokosta anchors the eastern end of this corridor, a 10-minute drive from Greenport's ferry terminal and walkable village center. The surrounding North Fork AVA produces cool-climate wines that benefit from the maritime influence—longer hang time, moderate ripening, and the kind of acidity that keeps white wines crisp and reds structured. The tasting room operates year-round, though the outdoor lawn closes in winter and service moves indoors to a smaller bar area. Spring and fall bring the most comfortable conditions for sitting outside, with lower humidity and thinner crowds than the July-August peak. If your schedule allows mid-week visits, Tuesday through Thursday see the lightest foot traffic. Weekend mornings remain the most reliable window for walk-ins, especially if you plan to pair your tasting with lunch from one of the food trucks that park on-site during high season.