WinterFest 2019

Winterfest 2019: Experience the Best of Long Island Wine, Music, Art and More!

By |Published On: February 22, 2019|

While Long Island may be better known as a summer getaway destination, there are still many reasons for a quick winter retreat to the Hamptons, especially during the 12th Annual Winterfest celebration on the East End.

Various local businesses and organizations are once again coming together to present the annual music, wine and performing arts festival which will run from February 22 – March 24, 2019.

The five-week celebration will take place throughout the East End at local wineries, breweries, performing arts centers, galleries, restaurants, hotels and more. From live concerts and winery tours to gallery exhibitions, book readings and comedy shows, there is something for everyone to enjoy.

Jazz on Long Island

Jazz on Long Island

Live Music & Concerts

The 2019 Winterfest will provide countless opportunities to enjoy live music here on the East End. Whether you prefer the sounds of jazz while sipping on a glass of wine, rocking out to the Stones or even a little country line dancing, there is something for everyone. Numerous wineries, breweries and restaurants will offer live music by local artists throughout Winterfest including Riverhead Cider House, Martha Clara Vineyard, Cooperage Inn and many more.

Additionally, local theaters will feature concerts paying tribute to many music legends from Tom Petty to Johnny Cash as well as an entire weekend celebrating the Beatles at Bay Street Theater on March 15 & 16.

Riverhead Farmers Market

Riverhead Farmers Market

Winery & Brewery Tours

Special winery and brewery tour packages will be available on various Saturdays during Winterfest. These packages include everything you need for a perfect taste of Long Island. The tours begin with a stop at the Riverhead Farmers Market and continue on to visit several wineries or breweries. Tours will also include a stop for lunch at a popular North Fork restaurant. Packages can be arranged to include accommodations and tickets to a Winterfest concert or performance as well.

Also, be sure to check out the special events that many East End wineries, breweries and distilleries will be hosting from live music to jewelry making classes. Test your knowledge at Jamesport Farm Brewery which will host Flights, Pints & Trivia Nights on Fridays throughout Winterfest or enjoy karaoke at Twin Stills Moonshine on Saturday evenings.

Mama Mia - Center Stage Southampton Cultural Center

Mama Mia, Southampton

Performing Arts & Comedy

If performance arts are more your scene, be sure to check out Mama Mia at the Southampton Cultural Center. Performances will run Thursday – Sunday from March 8 through March 24. The Cultural Center will be offering special Dinner & Theater or Brunch & Theater packages, available through their website.

The 2019 Winterfest will also feature comedic performances during All-Star Comedy Night at Bay Street Theater on Friday, March 22. Performers will include Corinne Fisher, Justin Silver, Moody McCarthy and Joseph Vecsey.

For additional laughter, Jamesport Farm Brewery will be hosting the Brewery Comedy Tour on Wednesday, March 13. This nationwide tour, featuring more than a dozen New York and L.A. comedians, is not to be missed as it makes a single stop here on the East End.


New to Winterfest in 2019, there will be several book signings with popular writers during the weekend of March 2 & 3. Authors include Sandra Block (What Happened That Night), Kristy Woodson (The Secret to Southern Charm), and Kelly Simmons (The Fifth of July).


Also, during Winterfest, take some time to enjoy the artwork of local East End artists at the William Ris Gallery. The gallery, along with the North Fork Art Collective, presents “New Year, New Works,” on view February 16 – March 10. Artists include Emma Ballou, Scott Bluedorn and Cindy Pease Roe among others. As part of the exhibition, the gallery will host an artist talk celebrating International Women’s Day on Friday, March 8.

The Hamptons Arts Network will also present the annual Thaw Fest during the final weekend of Winterfest, March 22 – 24. Enjoy many wonderful art exhibitions at participating galleries including the Pollock-Krasner House, Parrish Art Museum and the Southampton Arts Center. In addition to local exhibitions, Thaw Fest will also feature live music, film screenings and lectures.

Thaw Fest in the Hamptons

Thaw Fest in the Hamptons

With five weeks of special events, performances and so much more, Winterfest provides endless reasons to visit us on the East End this winter. Whether you are looking to escape the city for a weekend or just need something to do this Saturday, visit for a calendar full of events you don’t want to miss. Come experience the magic of Long Island during the “off-season.”