Sleepy Hollow Street Fair Extends Spooky Season into November 

Crowds pack Beekman Avenue during the annual Sleepy Hollow Street Fair. Photo: @sleepyhollowimages

The spooky season has been extended into November this year, as the Sleepy Hollow Street Fair welcomes visitors to the village’s historic haunted downtown on Sunday, Nov. 8. 

Beekman Avenue will be closed to cars from 10 a.m. to 5 p.m., creating a free, walkable day for visitors (and their pooches) to peruse arts and crafts stalls, food trucks and local shops with their doors propped open. 

The annual event, which draws thousands to the Hudson River Valley village, boasts 145 arts and crafts, food and beverage vendors, local eateries and businesses, as well as live music and children’s activities. Many local merchants will welcome visitors by setting up tables outside their stores. 

Rainouts in October prompted the Sleepy Hollow Tarrytown Chamber of Commerce to reschedule the popular event, giving the community and visitors one more chance to take in the quaint village’s seasonal flavor. 

“The Sleepy Hollow Street Fair is one of our favorite traditions because it truly brings out the best of our community,” Executive Director Lucia Ballas-Traynor said. “Whether you’ve lived here for generations or are visiting us for the very first time, there’s an extraordinary energy when our streets fill with local makers, eateries, and shops. We are thrilled to welcome everyone to celebrate the unique spirit and warmth that make Sleepy Hollow so special.” 

Some attendees come dressed in Halloween costume. Photo: @sleepyhollowimages

Entertainment schedule: 

  • Master Storyteller Jonathan Kruk: In front of Ganso Ramen on Beekman Avenue & Route 9/Broadway at 12 noon. 
  • Headless Horseman: In front of Ganso Ramen on Beekman Avenue and Route 9/Broadway from 1 to 4 p.m. 
  • Witches Along the Hudson: Beekman Avenue and Pocantico Street. Performances at 11:30 a.m. and 3 p.m. 
  • Luis Enrique’s Andean Flutes Band:  Beekman Lot at the top of Beekman and Route 9 
  • Village of Sleepy Hollow Kids’ Zone: located at Beekman Parking Lot. 

Live music presented by the BUMP at the Beekman Parking Lot Entrance: 

  • 11 a.m. – 12 p.m.: Scoot and Marlena of The Kulprits 
  • 12:15 – 1:15 p.m.: Brad & Nate – The Incumbents Acoustic  
  • 1:30 – 2:30 p.m. – the BUMP  
  • 2:45 – 3:45 p.m. – The Altogether  
  • 4 – 5 p.m. – Polish John 

The village will be opening the East Parcel Parking Lot at 60 Continental St., but parking is scarce and visitors are encouraged to take the train to get into the street fair. Two Metro-North stations (Tarrytown and Philipse Manor) are less than a mile from Beekman Avenue. Drivers are encouraged to park and board trains in Irvington, Dobbs Ferry, Croton Harmon or Hastings-on-Hudson.

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About the Author: Robert Brum