The North Fork Celebrates Winterfest 2022, from Live Music to Fine Dining

LI Winterfest at Jamesport Farm Brewery
LI Winterfest at Jamesport Farm Brewery
Barbara Lassen

It’s beginning to look a lot like Winterfest.

North Fork vineyards, breweries, lodging properties and other venues are rolling out live music, special menus, unique activities and discount packages for the annual celebration, which this year runs for the entire month of February.

Planning for Winterfest was tricky, with the Omicron variant of COVID-19 plowing through Long Island in January.

“Unfortunately, we’re working with a few challenges,” says lead organizer Diane Tucci, CEO of Main Street Agency in Riverhead. The annual Winterfest kickoff party, a social food-and-beverage sampling event whose goal is typically “to get as many people in the room as possible,” was canceled for the second year in a row, and some other events have been scaled back.

But compared with a year ago — when many venues were closed and live music was virtually nonexistent — Winterfest is getting back on track.

“We’re happy to see live music return for this year,” Tucci says. “You will find it at Hotel Indigo’s Bistro 72, Jamesport Farm Brewery and Twin Fork (Beer Company), among others.”

Bistro 72 — the restaurant in the Hotel Indigo in Riverhead — will have live music on Friday and Saturday evenings from 6–9 p.m., along with a special prix fixe Winterfest menu (in addition to the regular menu). The entertainment lineup will include Bakithi Kumalo on Saturday, February 26. The South African bassist, composer and vocalist, who is best known for performing on Paul Simon’s Graceland album, is a Winterfest veteran.

“Bakithi is one of our favorite performers, and he’s excited to be returning this year,” says Kristen Reyes, vice president of operations for the hotel.

The Jamesport Farm Brewery in Riverhead will be serving up live music on Saturday afternoons from 1–5 p.m., with artists Jay Shephard, Gene Casey, Wandering Time and Rob Europe on tap along with the brewery’s newest releases: Gentleman Joe, a porter, and The Kurgan, a Scotch ale. Looking ahead to March, the brewery is bringing back its annual Mardi Gras and Parrotheads vs. Deadheads events.

“These will also have live music, and costumes are encouraged,” adds Ashley Dunlop, tasting room manager.

Sannino Vineyard, which moved into a new tasting room on County Road 48 in Cutchogue in September 2019, has a February lineup that will include wine and doughnut pairings, wine and macaron pairings, trivia nights and a build-your-own-cheeseboard event.

“We usually see a lot of new faces for Winterfest,” says co-owner Lisa Sannino. “People are looking for things to do.”

With Valentine’s Day falling within the month, special themed events will include the ChocoVino-Valentine’s Dinner at the Long Island Aquarium in Riverhead on Saturday, February 12, featuring chocolate, wine and a five-course gourmet dinner amid the aquatic displays.

Continuing a pandemic-era trend, organizers will promote plenty of outdoor experiences for both visitors and locals.

“This was new for us last year and it was well-received, and so we’ll continue,” Tucci says.

Some venues have heated outdoor areas, like the Hotel Indigo, where revelers can sit on comfy sofas around the large outdoor fireplace and order from a special winter cocktail menu.

Originally a six-week event when it launched in 2007, Long Island Winterfest began with a focus on jazz and the North Fork vineyards, before expanding to other musical genres and venues as well as the broader region.

“Working in partnership with Discover Long Island, we began to take the event to the South Fork as well and expanded into the whole East End,” Tucci says. “Winterfest brought a lot of business to the vineyards, but eventually the craft breweries that have been popping up began to latch on to the concept, and over the past few years there have been more breweries hosting events than the vineyards.”

Today, the over-arching focus of Winterfest is to highlight the culture on the East End.

“We know thousands of people have been following Winterfest for almost two decades now and they are looking to come out here and find things to do, so we will keep providing the best resources we can as we find them,” Tucci says. “From music to hiking, it’s all about enjoying our beautiful part of the world in the winter.”

Long Island Winterfest runs February 1–28 across the North Fork and Hamptons. For more details, visit

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