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Deets: The Sleepy Hollow Street Fair is the village’s unofficial opening bell for autumn - a free, walkable Sunday on Beekman Avenue with the whole street given over to arts and crafts stalls, food trucks, local shops with their doors propped open, and a good deal of Halloween merchandise arriving a full six weeks early.

This family-friendly autumn kick-off event held on Beekman Avenue in Sleepy Hollow, New York, presented by the Sleepy Hollow Tarrytown Chamber of Commerce. The upcoming fair takes place on Sunday, September 20, 2026, from 10AM-5PM.

Hint for the Average Socialite: Learn more.

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