The village of Tarrytown, otherwise known as Sleepy Hollow, hosts one of the largest Halloween parades in Westchester County annually. This year, the village hosted its 22nd Halloween Parade on October 26th. The parade started at Tarrytown’s Patriots Park and moved along Broadway to Main Street, where a grandstand, food trucks, live band, and DJ awaited.

In The Legend of Sleepy Hollow, Wiley’s Swamp, modern-day Patriots Park, is where Ichabod Crane met the Headless Horseman. It is only fitting that the parade began here.

The parade consisted of dozens of themed floats, groups walking in costume, and marching bands. The Headless Horseman rode at the head of the parade; after all, it wouldn’t be Sleepy Hollow if he didn’t appear.

Each float and participant in the parade had the chance to win a prize. Prizes at this year’s parade included best neighborhood float, best adult, best float, best in show, best group, best child. This year’s winners were as follows:

The parade is planned every year by the Tarrytown Halloween Parade Committee within the Tarrytown Recreation Department. Dan Walczewski, Superintendent of the Rec Department. This year the parade was sponsored by 17 businesses; presenting sponsors were Phelps Hospital Northwell Health and DeCicco & Sons grocery store. Last month, Tarrytown held a fundraising event for the parade, and through social media, encouraged the community to donate. 

The parade has been steadily growing over the years, but this was the biggest yet. Over 10,000 visitors traveled to Tarrytown for the parade, creating traffic jams all along the Saw Mill Parkway, and  in Tarrytown and surrounding villages. Roads along the parade route were closed for the night, creating a difficult parking situation for the village. Visitors to the parade were encouraged to take alternative transportation, such as Metro North. Train and bus schedules were posted on the Tarrytown Halloween Parade Website. Despite this, hundreds of cars lined the streets of Tarrytown, and accessible parking lots were filled before the parade began.