It’s evident at Long Island wineries, where tasting experiences lean into both “taste” and “experiences,” that the vibes are as varied as the varietals. Some buzz with live tunes that redefine “wine notes” while others have tarot-card readers and even pig races. More still offer a chance to lounge by a fire pit, meet a winemaker or go full-on rosé. Indeed, there’s an experience for all tastes in Long Island wine country. So, if you want…
…to bring the kids
Harbes Vineyard (715 Sound Ave., Mattituck) Known for its apple orchard, pumpkin picking, and festivals spanning spring to fall, Harbes is also home to a vineyard stocked with award-winning wines made by winemaker Erik Bilka, who works alongside Ed Harbes IV.
…to introduce a wine newbie to tasting (or are one yourself)
Macari Vineyards (150 Bergen Ave., Mattituck) Founded in 1995, Macari Vineyards leaned into wine education well before it became a buzzword on the North Fork. It offers numerous by-appointment tasting experiences in its cellar, covered deck overlooking 500 acres of estate vineyards and private tasting suite for groups as small as two.
…to be entertained
Osprey’s Dominion (44075 Main Road, Peconic) Come for the live musicians, annual holiday fair, tarot-card readings and summer wagon that gives wine-in-hand tours of the lush vines; stay for winemaker Robin Epperson McCarthy’s excellent red blends.

…to experience modern vibes in a country-chic setting
Main & Mill (1291 Main Road, Jamesport) With its rich royal-blue couches, tidy geometric wine shelving and stunning copper light fixtures (compliments of the design eyes at Jamesport’s Lumber + Salt), Main & Mill feels like a new era in Long Island’s potato-barn past.
…to really feel like you’re on the NoFo
The Old Field Vineyards (59600 Main Road, Southold) With a property that dates to 1660, vintage North Fork is alive and well at this boutique family-run spot. Winemaker Perry Bliss and her mom, Ros Baiz, run their small tasting room from a charming old chicken coop where their flagship Commodore Perry Merlot is a must.
…to dig into OG history
Pellegrini Vineyards (23005 Main Road, Cutchogue) Purchased by North Fork pioneers Bob and Joyce Pellegrini in 1991, current winemaker, Cutchogue-born Zander Hargrave, is the talented progeny of parents Louisa and Alex Hargrave, who started the first Long Island winery in 1973 just steps from where he works today.
…to meet a winemaker
Chronicle Wines (2885 Peconic Lane, Peconic) Chronicle owners and winemakers Alie Shaper and Robin Epperson McCarthy are ever-present in the tasting room for winemaker happy hour each Monday from 4 to 6 p.m., during which guests receive 50-percent off and get the chance to mix and mingle.
…celebrity panache
Ev&Em Vineyards (3165 Main Road, Laurel) Political news wonk Dan Abrams opened Ev&Em in 2022, with Vanessa Price of Big Macs & Burgundy/TODAY fame signing on as the GM. Ev&Em’s winemaker is Byron Elmendorf, a local rising star in his own right whose pinot noir and cabernet sauvignon from the Classic Reds tier are the true crown jewels.
…quirky, sunny fun
Bridge Lane Wine (35 Cox Neck Road, Mattituck) One of the first in New York to embrace chilled-out mediums like wine in a can, in screw-top bottles, in a box and on tap, this Mattituck tasting room is all about being relaxed and having a good time, be it sipping with friends at rainbow picnic tables or playing a rollicking game of shuffleboard or cornhole.

…to be hip and sip rosé
Croteaux Vineyards (1450 S. Harbor Road, Southold) Pink is the heart and soul of Croteaux, where vinifera grapes grow on the vines for the exclusive purpose of making winemaker Alie Shaper’s excellent rosé in all shades, textures and preferences.
…to have a little pizza with your merlot
Palmer Vineyards (5120 Sound Ave., Riverhead) and Jamesport Vineyards (1216 Main Road, Jamesport) Palmer Vineyards and Jamesport Vineyards both have on-site wood-fired pizza that pairs beautifully with vino. Palmer’s is available at a food truck (lines can get long, but one bite and you’ll understand why), while Jamesport’s is made at an in-house restaurant.