Southold WinterFest 2024 Expands in Its Third Year

Clam shucking, flame throwing, fake snow, live music and plenty of free food and beverage samples are on the agenda for Southold WinterFest. The annual celebration is set for Saturday, February 17, from 10 a.m. to 3 p.m., with February 18 designated as a rain date.

Free to attend for locals and visitors, the popular event is centered around Main Road in Southold Village. It takes place both outdoors and inside several venues, including CAST (Center for Advocacy, Support and Transformation), the First Presbyterian Church, Southold Historical Museum, Southold Library and several restaurants and stores.

“This is our third annual WinterFest, and interest has grown each year,” says Brian Q. Smith, a member of the Southold Town Economic Development Committee, which stages the annual event. “It is the perfect venue for a business or organization to showcase itself. Each year we work to offer new things, add more entertainment and expand the number of exhibits, so it has grown a lot. Now, the word is out.”

Southold Fish Market returns for the third year with its popular clam shucking event. Led by Southold native Charlie Manwaring, the market is one of the most ardent supporters of WinterFest and is expected to shuck and serve up more than 1,000 free clams. Other local restaurants. along with vineyards and breweries, will provide free food and beverage tastings, including Maroni Cuisine, Latin Fuzion, Southold General, Southold Mediterranean Restaurant, The Giving Room, North Fork Taps and Corks, Eastern Front Brewery and Pindar Vineyards.

The long list of entertainers includes popular local bands and dance troupes. The Foster Europe Band and Jay Shepard Band are performing at the Village Green. The HooDoo Loungers and Lady T’s Highway Dancers are taking the stage at the First Presbyterian Church, with the latter giving line-dancing instruction. Over at CAST, the Caribbean Vibe Steel Drum Band and Lucy Kalantari and the Jazz Cats are providing the sounds. There is also a professional DJ and triple swing and cha-cha dance instruction.

The lineup includes typical festival diversions for kids and adults, including a caricaturist, crafting workshops, cupcake decorating, free drawings for gift baskets and jewelry, face painting and glitter tattooing, hair tinseling, a popcorn station and a selfie station. And there are some not-so-usual activities, like flame throwing.

“The flame throwing entertainment is new this year,” Smith says. “We wanted something fun and exciting. It includes a professional flame juggler and a magic show.”

Adding to the event’s ambiance is a snowmaking machine. “It will fill the air with beautiful, light, fluffy snow in the South Parking Lot, across from the Southold Library,” Smith says.

The Southold Town Economic Development Committee originally launched WinterFest to give locals a fun winter diversion and to show visitors that Southold is more than a summer destination. Organizers say nearly twice as many local businesses and organizations have signed up to participate in this year’s event versus 2023, and close to 2,000 attendees are expected.

For this year’s event, “we developed a more comprehensive list of potential exhibitors and took time to reach out to them via email, social media, press coverage and with personal follow-ups,” Smith says. “It also doesn’t hurt that there is no cost to a Town of Southold business or organization to participate! It’s a perfect way for them to promote themselves.”

The event also benefits from local charm and good timing.

“We think Southold’s Winterfest is so popular because it’s like an old-fashioned, hometown event,” says Jennifer Del Vaglio, a Southold Town Economic Development Committee member. “It includes terrific music, fun entertainment and activities for kids and adults, great food and lots of nice people. The merchants are all geared up. Everyone is happy and smiling. It’s also at the time of year — and on a holiday weekend — that folks are looking for something enjoyable and enriching.

There’s so many fun things to do, entertainment and exhibits to see, great food, lots of parking, and it’s free!”

What’s not to like?