Headless Horseman Hussle
Headless Horseman Hussle is a 5K race in Chicago, IL, held on Sun, Sep 20, 2026 at 898 Glen Oak Dr , with entry from $30. Headless Horseman Hussle takes place on September 20, 2026 in Sleepy Hollow, IL, with 5K on the schedule. Full details and registration are on the organizer's page.
| Date | Sun, Sep 20, 2026 |
| Distances | 5K |
| Venue | 898 Glen Oak Dr |
| Address | 898 Glen Oak Dr, Sleepy Hollow, IL |
| Entry | From $30 |
| Registration | Register for Headless Horseman Hussle |
Map location is approximate — confirm the start line with the organizer.
Listing updated Sun, Jul 26, 2026. Organize this race? Submit an update. Listing details via the organizer's page.
Racing Chicago? Get the drop.
Races like Headless Horseman Hussle sell out — get new Chicago races twice a month plus price-jump warnings.
More races in Chicago
- Sun, Jul 26, 2026 Fulton Market Loop Da Loop 5k
- Sat, Aug 1, 2026 Hoofin' it for Ag 5K
- Sat, Aug 1, 2026 Dim Sum & Then Some: The Uptown 5K/10K & Kids Dash
- Sat, Aug 1, 2026 Nick Schultz LLG