Discover the magic of autumn at the Sleepy Hollow Street Fair, presented by the Sleepy Hollow Tarrytown Chamber of Commerce! On Sunday, September 21, immerse yourself in a bustling community event with nearly 200 vendors showcasing a diverse array of crafts, cuisine, and local delights. From handmade treasures to delectable treats, there’s something to enchant every visitor. Enjoy live music, family activities, and the vibrant atmosphere of downtown Sleepy Hollow. Join us for a day filled with community spirit, festive fun, and an appearance by the Headless Horseman!

Fall 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 third weekend of September, be sure to stop by the Sleepy Hollow Street Fair!

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

2025 Date: Sunday, September 21, 10 am to 4 pm.

Where: Beekman Avenue, Sleepy Hollow, NY 10591 (Between Pocantico Street and Broadway)

For info: 914-631-1705, https://www.sleepyhollowtarrytownchamber.com

Learn More @SleepyHollowFallFest