Autumn in New York is incomplete without a trek to the Sleepy Hollow Fair — just ask the 5,000 annual visitors who flock to Beekman Avenue.
The Hudson Valley town celebrates its local community and spooky roots every year as the seasons change and our favorite creepy holiday approaches. We honestly couldn’t think of a more welcoming way to head into the fall equinox.
If you’re one to indulge in all-things pumpkin and can’t resist the charm of a Halloween town, we’ll see you on the Metro-North.
All about the Sleepy Hollow Fair 2025
This year’s event will take place on Sunday, September 21st with the festivities getting underway bright and early at 10am.
Unlike your typical street festival, this event draws in close to 200 local vendors who come equipped with handmade trinkets, delicious bites, and but of course, seasonal decorations that are nothing short of “bootiful”. In addition to shopping, attendees can expect music, family activities, crafts, and much more. Should you be interested, furry friends are also welcome.
Nearby eateries will be ready and willing to keep fair-goers fueled and energized, including: Casaletto Pizza, ChuChok Thai, The Taco Club, and beyond. Plus, businesses in town, including the witchy accessory shop Cozy Coven and the family-focused Sleepy Hollow Bookshop, will be ready to welcome guests.
Perhaps more exciting than the fair itself would be the highly-anticipated Headless Horseman appearance! For those unfamiliar with the town lore, writer Washington Irving not only lived in the town back in the 1800s, but he used it as information for his creepy literature. Though there’s no word on when or where the Headless Horseman will appear, we can assure you that you don’t want to miss him.
Given that New Yorkers claimed the Hudson Valley hotspot as their favorite fall getaway — courtesy of its quaint charm, gorgeous grounds, and rich history — we’d say a trip is still a must this fall, even if you can’t make it to the festival.
Visit the Sleepy Hollow website to learn more about what’s ahead – shows, pumpkin patches, farmers markets, and of course, the Great Jack O’Lantern Blaze.
🗓️ Sunday, September 21st
⏰ 10am-4pm
📍 Beekman Avenue, Sleepy Hollow (Between Pocantico Street and Broadway)
Looking for a quick escape? Our favorite day trips and excursions from NYC are worth exploring!