Sleepy Hollow 10K
Sleepy Hollow, NY
Oct 24, 2026
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… The course … MORE
Local Historical Weather (Oct 24):
| 2025 | 2024 | 2023 | 2022 | 2021 | |
| H (°F) | 58 | 68 | 62 | 61 | 56 |
| L (°F) | 42 | 53 | 42 | 53 | 42 |
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A must do
This is one of those races I come back to every year since it's so much fun to see everyone is costume and to watch the kids' race before the … MORE
This is one of those races I come back to every year since it’s so much fun to see everyone is costume and to watch the kids’ race before the 10k starts. There’s pretty good support from local residents and since it’s in Sleepy Hollow there’s not a lack of Halloween spirit. I wouldn’t mind getting a medal, but since I always have such a fun time, it’s not entirely missed. The post race spread is great and the pre race packet pickup is super easy either morning of or in advance at Westchester Road Runners. This is one that I’ll keeping coming back to especially since the headless horseman always makes an appearance.
Spooky Small Town Gem
Beautiful day! Weather was unseasonably warm so I had to change my outfit plans, but aside from that it was great. Great costumes, neighborhood support, scenic course (with some killer … MORE
Beautiful day! Weather was unseasonably warm so I had to change my outfit plans, but aside from that it was great. Great costumes, neighborhood support, scenic course (with some killer hills). Fun long sleeve shirt design. Plenty of post race food/drink. A fun kid’s race. Ample free parking. Will definitely be adding this one to my list of yearly races.