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Sleepy Hollow Halloween 10K & Kids Fun Run

October 26 @ 9:30 am - 12:00 pm

$40 – $50
The headless horseman leads the start of Sleepy Hollow Halloween 10k.

Enjoy a remarkable course that takes you through Historic Sleepy Hollow’s treasured sights including a stretch along the Hudson River with views of the Headless Horseman Bridge, Sleepy Hollow Cemetery and the Old Dutch Church. You never know what might be lurking on the course in Sleepy Hollow…

Registration is limited to the first 2000. Costumes are encouraged but not required. There’s fun for the whole family: live music, beer tasting for all runners 21 and older, a Kids’ 1 mile Fun Run for those 6 and older–$5 includes finisher medal.

The Sleepy Hollow Halloween 10K race was voted one of the best Halloween 10Ks in the country by Runners World Magazine. Everything from the Halloween-inspired race shirts to the age group medals and the post-race festivities, it is all about celebrating Halloween in Sleepy Hollow. Even the Kids Fun Run finisher medals have pumpkins on them!  The Headless Horseman helps with the start of the race and can be seen again at mile 2. There is music throughout the course for the runners to enjoy. Many homeowners who have decorated their homes are along the course cheering and admiring the many different costumed runners.

After the race enjoy the best post-race grub around. No dry bagels at this finish! There are local pastries from our Chilean bakery, Boxed Water is Better, and multiple protein and granola bars. And yes, there is candy, it is Halloween after all. For those of age there is a complimentary draft beer and there is also non alcoholic beer from Athletic Brewing Company. The post run costume contest is always a blast because the costumes are awesome.


October 26
9:30 am - 12:00 pm
$40 – $50
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Rivertown Runners
View Organizer Website


Morse School
30 Pocantico Street
Sleepy Hollow, NY 10591 United States
+ Google Map

There’s something for everyone in Sleepy Hollow Country—farmers markets, live music, street fairs, historic homes, hiking trails, kayaking and boating on the Hudson River. Halloween season brings even more for the whole family—haunted hayrides, blazing pumpkins, costumed 10K run, Halloween parade, and of course, the Headless Horseman! For the latest on Fall events, visit our guide to Halloween in Sleepy Hollow.