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Due to weather forecast, the Chamber of Commerce has postponed this event to Sunday, October 15.

Sleepy Hollow Street Fair

October 14, 2023 @ 10:00 am - 4:00 pm

Sleepy Hollow Street Fair tent by J & G Deli features baked goods.

Pet friendly rooms available at this hotel.The Sleepy Hollow Tarrytown Chamber of Commerce’s annual Sleepy Hollow Street Fair takes place this year on Saturday, October 14th, transforming Beekman Avenue into a huge outdoor market. Nearly 100 vendors draw thousands of visitors!

October is the most exciting time to visit Sleepy Hollow. The weeks leading up to Halloween have something for everyone: haunted hayrides, Gothic mansions, blazing pumpkins, farmers markets, live music, 5K run (costumes welcome!), Halloween parade, and of course, the Headless Horseman! If your visit includes the second weekend of October, be sure to stop by the Sleepy Hollow Street Fair where you will find food, music, local retailers, arts & crafts, plus Halloween and Holiday items!

Explore more local shopping at Tarrytown’s and Sleepy Hollow’s galleries, gift shops and antique stores.


October 14, 2023
10:00 am - 4:00 pm
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Beekman Avenue, Sleepy Hollow
Beekman Avenue
Sleepy Hollow, NY 10591 United States
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There’s something for everyone in Sleepy Hollow Country—farmers markets, live music, street fairs, historic homes, hiking trails, kayaking and boating on the Hudson River. Halloween season brings even more for the whole family—haunted hayrides, blazing pumpkins, costumed 10K run, Halloween parade, and of course, the Headless Horseman! For the latest on Fall events, visit our guide to Halloween in Sleepy Hollow.