Autumn returns to New York next month, bringing back the beloved fall festival adorned with 200 vendors, tantalizing local delicacies, and the spine-tingling presence of the Headless Horseman.
On Sunday, September 21, 2025, the picturesque town of Sleepy Hollow will transform into a vibrant autumnal hub with the arrival of the Sleepy Hollow Halloween Fair. From 10 am to 4 pm, Beekman Avenue, between Pocantico Street and Broadway, will come alive with approximately 200 local vendors, food stalls, and family-friendly activities.
Visitors can look forward to a diverse range of offerings, including handmade trinkets, seasonal decorations, and delicious food from local eateries such as Casaletto Pizza, ChuChok Thai, and The Taco Club. Nearby businesses, including the Cozy Coven witchy accessory shop and Sleepy Hollow Bookshop, will also be open to welcome guests.
The fair promises an exciting atmosphere with music, family-friendly crafts, and the anticipated appearance of the Headless Horseman, a legendary character deeply rooted in Sleepy Hollow's history and Washington Irving's spooky literature.
The event is not only a celebration of the season but also a showcase of local culture, making it a must-visit for those seeking a robust fall festival experience. Pets are welcome, adding to the family-friendly, pet-welcoming vibe of the day.
For more information, visit the Sleepy Hollow website. If you're planning a day trip, consider exploring other attractions in the area. This year, eight Spirit Halloween stores are open in NYC, according to a separate article, providing additional Halloween-themed experiences.
As the days get cooler, Sleepy Hollow offers a variety of seasonal activities, including pumpkin picking, hayrides, and farmers markets. Later in the season, the town hosts more theatrical, nighttime experiences like Twilight Village with live storytellers, fire performers, and dramatic Headless Horseman performances after dark in October.
Whether you're a fan of Washington Irving's tales or simply looking for a unique fall outing, the Sleepy Hollow Halloween Fair 2025 promises an unforgettable experience.
With the excitement of the Sleepy Hollow Halloween Fair, visitors might experience a fever of anticipation as they immerse themselves in the vibrant autumnal atmosphere, transforming their lifestyle temporarily into a home-and-garden festival enthusiast. After enjoying the fair, travelers can consider extending their trip to explore other Halloween-themed experiences available at Spirit Halloween stores across NYC or engage in seasonal activities like pumpkin picking, hayrides, and farmers markets which Sleepy Hollow offers.
