Broadway shows have returned, Yankee Stadium and Citi Field are full of fans, but nothing says fall is back in swing in the region quite like the return of Halloween season events in Sleepy Hollow, NY. The Village, which recently marked the bicentennial of Washington Irving’s “The Legend of Sleepy Hollow,” published in 1820, had to put Halloween events on hiatus last year, but has an exciting slate of outdoor events and celebrations planned for the upcoming season.
Village of Sleepy Hollow Mayor Ken Wray commented, “Sleepy Hollow has emerged as a year-round destination, and is a great place to live and work – but we know that people across the country and around the world are particularly drawn to the Village during Halloween season. So, we’re all in! We’re mindful that safety protocals remain important, and therefore, Sleepy Hollow and neighboring villages and organizations have developed outdoor-only events that can accommodate visitors.”
Sleepy Hollow bears the name made famous in Irving’s 19th century story. The spooky tale of a headless horseman and his pursuit of schoolteacher Ichabod Crane has become synonymous with the Halloween season. While fictional, Irving’s tale featured actual local landmarks that visitors continue to flock to, even two hundred years after the story’s publication. These include the Old Dutch Church of Sleepy Hollow, built in 1697, as well as the adjacent Sleepy Hollow Cemetery, in which Irving himself lies buried. Washington Irving’s historic home, “Sunnyside,” located in nearby Tarrytown, hosts tours and special events, as well.
There’s nothing quite like the Halloween Season in Sleepy Hollow, which has grown in recent years to give Salem, MA a run for its money as the nation’s Halloween capital. Marketing a broader stretch of the Hudson River Valley in Westchester County as “Sleepy Hollow Country” (from Tarrytown and Sleepy Hollow as far north as Croton-on-Hudson) the area draws hundreds of thousands of visitors to events from September through Halloween and into November.
Highlights of Special Events during the 2021 Fall and Halloween Season in “Sleepy Hollow Country”
- Daytime Walking Tours of Sleepy Hollow Cemetery + Evening Lantern Tours (September-November). Advance reservations required, tickets and details at visitsleepyhollow.com
- The Great Jack O’Lantern Blaze: September 17 – October 31, November 3-7, 10-14, 18-21. A breathtaking display of more than 7,000 illuminated Jack O’ Lanterns outdoors on the grounds of historic Van Cortlandt Manor in Croton-on-Hudson, NY. Advance reservations required, tickets and details at https://hudsonvalley.org/events/blaze/
- P. Doyle’s Sleepy Hollow Block Party: September 18, 2:00pm – 9:00pm. Don’t miss the action on Beekman Avenue with this block party featuring live music including Shilelagh Law; Niall and the Durty Nellys; and The Incumbents. Food trucks, kids attractions. www.jpdoyles.com
- Oktoberfest at Kingsland Point Park, Sleepy Hollow: Saturday, Sept. 25, 1pm to 5 pm Enjoy a day of music, food, bouncy castles and refreshments. Admission is free (parking requires a separate fee). sleepyhollowny.gov
- The TaSH Farmers Market: Saturdays from 8:30am – 1:30pm at Patriots Park (through November 20)
Special Halloween-themed activities throughout the fall! Learn more at tashfarmersmarket.org
- Sleepy Hollow Cultural Festival: October 2, 10:00am – 6:00pm at Kingsland Point Park
A celebration of the many cultures represented in Sleepy Hollow including performances of traditional dance, live music, food and a community arts exhibition. www.sleepyhollowny.gov
- The Historical Society of Tarrytown and Sleepy Hollow: Walking Tours Sept. and Oct. Weekends
Tours include “Irving, the Old Dutch Church and the Colonial Experience,” “Heroes and Villains,” and “Walking Through Time.” Advance reservations required: www.thehistoricalsociety.net
- Irving’s ‘Legend’ Under the Stars at Sunnyside: 1-31, Fridays-Sundays at 6:30, 8, and 9:30pm
Performed for the first time ever outdoors under the stars at Washington Irving’s Sunnyside, storyteller Jonathan Kruk casts a spell with performances of the classic tale. Live music and an appearance from the Headless Horseman make this a spectacular experience for all ages. Advance reservations are required. https://tickets.hudsonvalley.org/events
- Sleepy Hollow Street Fair: October 10. Beekman Avenue, Sleepy Hollow 10am – 4pm. https://www.sleepyhollowtarrytownchamber.com/
- Sleepy Hollow International Film Festival: October 15, 16 and 17. This year’s festival features “Drive-in” movies after dark at Kingsland Point Park along the Hudson River waterfront in Sleepy Hollow. Friday’s opening night double feature kicks-off with John Carpenter’s masterful THE THING. sleepyhollowfilmfest.com
- Sleepy Hollow Haunted Hayride and Block Party: October 22-23, 5:00pm – 11:00pm
The Haunted Hayride rides again into the dark night where ghosts and goblins loom. Timed entry, advance purchase recommended. Afterwards enjoy the annual block party with vendors, food, and music. Covid 19 restrictions may apply. www.sleepyhollowny.gov
- Sleepy Hollow 10K Halloween Run: October 23. Kids Race 9:00 am, 10K 9:30am at Morse School Enjoy the history and scares of Sleepy Hollow as you run-for-your-life-along the scenic Hudson Valley course. Don’t forget to dress up as BEST COSTUME wins! Advance registration available at rivertownrunners.org.