On Saturday, February 21, Southold Winterfest brings the community together along Main Road in Southold for a lively winter celebration featuring live ice sculpting, music, local shopping, and family-friendly activities. Hosted by the Southold Town Economic Development Committee, the event highlights local businesses and makers while offering a festive way to spend a winter afternoon outdoors. Ideal for families, visitors, and locals alike looking to shake off winter and enjoy the season with the broader North Fork community.