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The Headless Horseman Ride to Sleepy Hollow

About this event



On a brisk Fall Saturday, we celebrate Halloween by visiting the home of Washington Irving and the Sleepy Hollow Cemetery where he is buried. Washington Irving is the famous early 19th century author of “The Legend of Sleepy Hollow” with its infamous character, the Headless Horseman.

 

Instead of a Halloween costume, wear your most colorful and wildest bike jersey. There will be a Prize for the person with the wildest jersey as voted on by the group.

 

We begin at West 242nd Street and Broadway (at the end of the No. 1 Subway) and meet just inside Van Cortlandt Park. We ride East across the bottom of the park, then North to the Old Putnam/South County Trail for about 10 miles. Heading West we cross the Sawmill River Parkway at Lawrence Street and wind through the suburban streets of Dobbs Ferry ending at the Old Croton Aqueduct. We ride North on a short portion on the OCA to East Sunnyside Lane and down the hill to see Washington Irving’s house, Sunnyside, and the visitors center for a restroom stop. Unfortunately we can’t go onto Sunnyside’s grounds and see the house up close without paying a fee, so we’ll see the house from a distance.

 

Back to the OCA we continue North to the Riverwalk to its end, then ride up to Broadway and through Tarrytown to the Sleepy Hollow Cemetery. Inside the cemetery is the Old Dutch Reformed Church, where Mr. Irvington’s book states that the Headless Horseman is “buried” in its graveyard. We’ll walk up the path to view the Washington Irving’s grave. 

 

Afterwards we’ll ride South on Broadway for lunch in Tarrytown. Then we ride East on Route 119 to the South County Trail where we retrace our route back to Van Cortlandt Park and Broadway at West 242nd Street.

GPS map: https://ridewithgps.com/routes/44847343
Cue sheet: http://snuggl.es/roboviva/pdfs/44847343.pdf

Ride is co-listed with NYCC.

Check your email before setting out. Any changes will be emailed to participants by 7:30 AM on the morning of the ride. 

 

Date and Time

Saturday, October 25, 2025, 9:30 AM until 4:00 PM

Location

Van Cortlandt Park -
Last stop on 1 subway train; Also accessible from 4 A D (1–2 miles away).
Broadway at West 242 Street
Bronx, NY  
USA

Ride Leader(s)

John D Kolenda

Jim Zisfein

Category

Moderate Rides 12-15 mph

Mileage:

36

Endpoint:

Registration Info

Registration is required
Registration cancellations will be accepted

Capacity

10 Total Slots
6 Available Slot(s)