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WinterFest returns to Southold Feb. 21

By Brendan Carpenter

WinterFest blows back into Southold on Saturday, Feb. 21, 2026. (Credit: Jeremy Garretson file photo)

Grab your hats and gloves, because the fifth annual WinterFest blows back into Southold on Saturday, Feb. 21, 2026, organizers of the popular event announced Thursday, Dec. 4.

Local merchants, live music and dancing will take over Main Road in Southold Hamlet from 10 a.m. to 3 p.m.

The “Norman Rockwellesque” event celebrates Southold’s community members and promotes its local businesses and groups.

Over 50 exhibits from area shops and organizations, and more than 2,500 people are expected to bundle up and take part in the free celebration.

  • Dan Bergin with Apple Ice showed off his skills by scultping dragons and sharks. (Credit: Jeremy Garretson file photo)
  • Four bands will hit the stage at next year’s WinterFest. (Credit: Jeremy Garretson file photo)

Throughout the five-hour jubilee, attendees will be able to hear music from four bands and take part in line dancing, face painting and more. There will also be free food and beverages, as well as prizes.

Last year’s edition saw impressive ice sculptures by Dan Bergin with Apple Ice. Dragons and sharks were among his frozen artwork.

Space is limited for the event, so any Southold Town businesses or groups wanting to take part should contact the town’s economic development committee at [email protected].

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