Winterfest 2018 Packs in Four Weeks of Live Music, Wine and More

Winterfest 2018 wine corks
Winterfest 2018 is coming! Photo: belchonock/123RF

Long Island’s ultimate pairing of wine and music, Winterfest, is back for 2018 starting next week. The annual monthlong event is a festival of live music, local art, culture, wine, craft brews and community spread throughout venues around the Twin Forks.

This year’s Winterfest 2018 begins with a Happy Hour and free live music by April Rain at Hotel Indigo East End in Riverhead (1830 W. Main Street) on Thursday, February 22 from 5–9 p.m., but the official kickoff party (7–10 p.m.) really gets things going the following night with rocker Keith Sloan (5–9 p.m.) at Hotel Indigo’s Bistro 72. At the same time in Sag Harbor, Bay Street Theater’s All Star Comedy Show begins a night of stand-up at 8 p.m. Greenport Harbor Brewing Co. will also host free live music by Points East that night from 6–9 p.m. in their Peconic location (42155 Main Road).

From there, Winterfest 2018 follows with four solid weeks of activities at 27 participating Hamptons and North Fork venues, including wineries, bars, restaurants, breweries, art galleries, theaters and more. There’s so much happening on any given day, it may be hard to choose which events to attend.

On Saturday, February 24, the fun begins early with a Brews for Bret fundraiser at Jamesport Farm Brewery from noon to 9 p.m. Long Ireland Brewery in Riverhead has a Whiskey Weekend beer release from 1–6 p.m., while Clovis Point vineyard has a Private Wine Tasting with their winemaker in Jamesport (1935 Main Road), Wolffer Estate in Sagaponack (139 Sagg Road) holds a VIP Tour and Barrel Tasting, and Martha Clara in Riverhead (6025 Sound Avenue) has a Wine Master Class—all starting at 1 p.m.

The Saturday festivities continue with live music at Palmer Vineyards, Karaoke at Twin Stills Moonshine in Riverhead and an opportunity to meet North Fork Chocolate master chocolatier Steve Biscari in Aquebogue. And that’s only about half of the day and evening events!

Sunday, February 25 offers yet another full day of tastings, live music, releases and more, starting with a ride on the North Fork Trolly at 11 a.m.—it’s the safest way to travel when going from event to event, and drinking along the way.

Winterfest 2018 goes on like this through Sunday, March 18, so it’s going to take some careful consideration to choose between must-attend events and the ones to skip. Get a feel for things next weekend and then visit for a complete schedule and details, or view the embedded 2018 Winterfest Festival Guide below.

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