Frosty Fun Unfolds At Southold's 4th Annual WinterFest: Photos

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SOUTHOLD, NY — It was a scene straight out of a Norman Rockwell painting: The streets of Southold were alive with music, food, dance and community Saturday, with residents strolling along Main Road, visiting shops and enjoying the heart and soul of small town life.

Crowds gathered as the Southold Town economic development committee presented its 4th Annual WinterFest, an event that brings the community together in the heart of the hamlet — and judging by the many that turned out, the event has grown into a beloved annual event.

WinterFest celebrates the community of Southold and promotes its many local businesses and organizations.

WinterFest 2025 included live entertainment, free food and beverage samplings, fun activities for adults and children, special events and prizes.

Southold Town's economic development committee was created by the Southold town board to advance initiatives that support economic growth for residents and businesses The volunteer committee is charged with promoting economic vitality, as outlined in the town’s comprehensive plan.