5th Annual Winterfest Set To Transform Southold Into Norman Rockwellesque Wonderland

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SOUTHOLD, NY — What's quickly becoming one of the most beloved events of the winter season on the North Fork will soon be back, as the 5th Annual Winterfest unfolds in Southold.

This year, the event takes place on Saturday, February 21, from 10 a.m. and 3 p.m. on Main Road in the hamlet of Southold; a rain date has been scheduled for February 22. Hosted by the Southold Town Economic Development Committee, Winterfest feels to attendees like something straight out of Norman Rockwell, bringing the community together for small-town frosty fun.

Winterfest celebrates the community of Southold and promotes its hometown businesses and organizations, organizers said. Scores of local businesses and organizations and more than 2,500 people are expected to take part.

The event is free to all visitors and Southold businesses and organizations.

Together with participating Southold hamlet merchants, WinterFest 2026 will bring the community to life with 50-plus exhibits from local businesses and organizations. Festivities will include ongoing live entertainment, four bands, face painting, line dancing, free food and beverages, DJ music, fun activities for children, and special events and prizes.

Space is limited and Town of Southold businesses or organizations interested in sponsorship and / or participation should contact the EDC at southoldwinterfest@gmail.com as soon as possible.

The goal of the EDC is to advance initiatives that support economic growth within the Town of Southold as outlined in the Town’s Comprehensive Plan, “Southold 2020.”