Second annual Winterfest returns to Southold on Feb. 18

In a townwide effort to attract year-round tourists, Southold will host its second annual WinterFest Saturday, Feb. 18, from 10 a.m. to 4 p.m.

“We want to show that Southold is a year-round town,” said Jack Malley, chair of the town’s economic development committee. “It’s not just a seasonal place to visit. The majority of the wineries are still open, bed-and-breakfasts are still available, there’s a lot to do on the North Fork during the winter months.”

WinterFest will involve many local businesses and organizations. The Center for Advocacy, Support and Transformation and First Presbyterian Church, for example, will host multiple activities throughout the day, such as face painting, cookie decorating, a magic show, live music and flamenco dancing.

“We want to bring something new and exciting to the community,” said Cathy Demeroto, executive director of CAST. “We want to provide a place for people to get warm, have some fun and see some interesting acts. We did the WinterFest last year and we’re happy to participate and work together to bring some fun activities for families.”

The idea for a festival in mid-February was presented by the economic development committee in early 2020 but was shelved when the pandemic shut down New York State. The Town Board created the EDC in 2011 to “advance initiatives that support economic growth for residents and businesses within the Town of Southold,” according to a press release. The committee consists of nine volunteers, who are excited to be holding this event for its second consecutive year.

“We expect participation to double,” said Mr. Malley. “Last year between 500 and 600 people joined us, and we hope to see over a thousand visit the event throughout the day this year, if not more.”

The event is free to all residents and visitors. Businesses along Main Road in Southold will be open for shopping and will also serve as warming locations. A rain date is set for Sunday, Feb 19.