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Southold Winterfest

  • Main Road, Southold Main Road Southold, NY United States (map)

The 5th Annual Southold WinterFest is officially back on Saturday, February 21st, 2026!

Get ready for the ultimate winter block party. We’re transforming Southold Village into a winter wonderland from 10 AM - 3 PM.

📍 Where: Main Road, Southold
📅 When: Sat, Feb 21 | 10 AM - 3 PM (Rain Date: Feb 22)
🎟 Admission: FREE!

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February 20

GDC Roller Skate Rink All Skate Sundays: Winter Break

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February 21

Reptiles at Southold Library for Winterfest