Southold WinterFest

The annual "Norman Rockwellesque" event celebrates the community of Southold Scores of local businesses and organizations and more than 1,500 visitors are expected to participate, organizers said. Southold WinterFest: Main Road in Southold Village, Saturday February 8, 2025, 10:00 AM to 3:00 PM. Three bands, DJ, dancing, fun entertainment for all ages, 50 exhibits, food trucks, free food and beverage samples, gift baskets, and more.