Sleepy Hollow/Tarrytown Halloween Skate and Parade

The leader for this event is Westchester Collar "Moonman" Pete!

We group up from 8:15 a.m. to 8:45 a.m.

WE SKATE OFF AT 9:00 A.M. SHARP!!

This is a LONG DISTANCE, INTERMEDIATE to ADVANCED LEVEL SKATE EVENT of approximately 32 miles from the Lincoln Center area in Manhattan to Sleepy Hollow in Westchester County, NY (This event description will be followed by another with options to meet us along the route in upper Manhattan or the Bronx if you prefer fewer miles or a later start time, but space cannot be guaranteed in the sag wagon for costume parts and bags if you do not skate with us from the event's starting point.)

Much of the route will be on trails including the Hudson River Greenway and/or the Riverside Park paths and the South County Trail which we can now access from the newly-paved trail in Van Cortlandt Park in the Bronx. We WILL have a sag wagon. For many years, RON and JAN have been kind enough to volunteer their cars and time to make the journey more comfortable for their skater friends. Ron Tow is back again this year to volunteer his time and car to help make this event happen.

The Tarrytown Parade Committee has invited us back to roll in the parade as we did in 2017, 2019, 2022, 2023 and 2024 and 2025. Both Tarrytown and Sleepy Hollow go all out with decorations and create a very festive atmosphere for their visitors and those who participate in and attend the parade.

THE SKATE: Join MOONMAN PETE as he leads a group of costumed skaters north from Manhattan to the Old Dutch Church and the Sleepy Hollow Cemetery in Sleepy Hollow, NY to chase down the Headless Horseman, the fictional character from Washington Irving's Classic story, "The Legend of Sleepy Hollow". The remains of author Washington Irving lie in the cemetery and, according to legend, so do the remains the Headless Hessian Horseman, who apparently rises up each evening and gallops through the village in search of the head that he lost in battle.

In recent years, the skate has started out on the paths and trails of Riverside Park, the Hudson River Greenway, and the Harlem River Greenway and continued through Inwood in upper Manhattan until we cross over to the Bronx via the Broadway Bridge. After a few miles of street skating in the Bronx, we return to the serenity of the colorful autumn trails as we enter Westchester County’s South County Trail and follow it all the way to Dobbs Ferry, NY. At that point, we skate west to the Hudson River and roll north through several river villages until we reach our destination – the Old Dutch Church and the Sleepy Hollow Cemetery.

Traditionally, we gather for a meal at Osaka in Tarrytown between 2:30 and 3 p.m. after we finish skating and before we enter the parade, but you can eat elsewhere or choose to explore the villages instead. The Tarrytown Parade begins around 5 p.m. and concludes around 6:30 p.m. The Metro-North train from Tarrytown to Manhattan is nearby and provides an express trip back to Grand Central of approximately 50 to 60 minutes.

More details about the event, including meet-up options, the route, and the post-skate gathering will follow shortly as an addition to this event post.

HALLOWEEN ON WHEELS is coming soon….get busy with the costume creation, get yourself fit for the skate and the parade, and join the Empire Skate Club as it celebrates one of the year's best holidays on skates!