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Sag Harbor Express / Community Story / 2410262

Sag Harbor Lights Up on Friday

authorStaff Writer on Dec 1, 2025

The holiday season in Sag Harbor officially begins on Friday, December 5, with the annual Light Up of the windmill on Long Wharf — a beloved village tradition that draws families, neighbors and visitors to the harborfront. The festivities kick off at 4:15 p.m., when Sarah Conway — known fondly as “Ms. Christmas” — and the Playful Souls fill the air with classic holiday tunes from the courtyard of Bay Street Theater. Guests are encouraged to gather early, warm up with the music, and join in the community sing-along.

At 5 p.m., the iconic windmill will be illuminated, marking the start of the season with a bright, festive glow over the waterfront. All are welcome to attend this free, family-friendly celebration presented by the Sag Harbor Chamber of Commerce.

More information is available at sagharborchamber.com.

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