Headless Horseman Reined In; Will Not Be Appearing in Village of Warwick

By Katie Bisaro

The Headless Horseman – which had become an annual fall tradition – will not be making its appearance this year in the Village of Warwick as it has in past years. Leora Dillon, the rider from the Corinthian Equestrian Center, was unable to secure the proper insurance in order to make the annual ride down Main St. in the Village of Warwick.

The Village Board of Trustees, during a Special Meeting held on Thurs., Oct. 15, discussed the popular attraction with regards to the need for insurance as well as the “overarching issue” of the ongoing COVID-19 pandemic.

In the past, the Headless Horseman made its appearance randomly and unannounced down the middle of Main St. in the Village of Warwick. This year, however, Dillon, as the Headless Horseman, and a companion rider appearing as the Grim Reaper, scheduled and published their appearances in advance creating the potential for crowds to gather. 

  In the view of the Village Board, the appearances were now a scheduled “event” and as such subject to Board approval and a certificate of insurance requirement. Moreover, a scheduled event encourages crowds to gather which, under COVID-19 restrictions and guidelines, is not desirable. The Village’s annual Halloween Parade has been cancelled as well due to the same crowd gathering concerns. 

Village Attorney Stephen Gaba, acknowledged the history of the Headless Horseman appearances and that other villages were allowing them to ride on their streets.

“In my view, this is an event. [Dillon] needs Village permission and she absolutely should have insurance. There are a lot of things that could go wrong with having someone ride down [Village] streets on a horse, particularly if you have people lining the sidewalks,” Gaba stated.

He pointed out that although the Village has insurance, it is not unlimited insurance and the Village should have a policy from Dillon as well. 

“It is not illegal to allow someone to conduct an event without having insurance, but it is, however, unwise to do that,” Gaba said.

Gaba also commented that due to the popularity of past Halloween events, crowds would inevitably gather for the scheduled rides and it would be hard to control and enforce social distancing and mask wearing, which could subject the Village to possible fines from the State.  

It was also pointed out that the scheduled appearances coincided with the outdoor dining that takes place on Main St. on the weekends. Trustee George McManus suggested altering the riders’ route down South St. to Railroad Ave. would solve that problem, but the insurance issue remains. 

Although already cancelled for this year, in past years the popular holiday-season horse and carriage rides were also required to provide additional insurance and receive Board approval for their events. 

At the regular Board of Trustees meeting on Mon., Oct. 19, the Board held a brief discussion on the matter, but since Dillon was unable to provide the necessary insurance, the appearances of the Headless Horseman will not take place in the Village of Warwick this year.  

The Headless Horseman, seen here as part of the Village’s Halloween Parade last year, will not be riding in the Village of Warwick this year due to insurance requirements & concerns about crowds gathering due to the ongoing COVID-19 pandemic.