| Tom Mison | Ichabod Crane |
| Nicole Beharie | Abbie Mills |
| Orlando Jones | Frank Irving |
| Katia Winter | Katrina Crane |
| John Cho | Andy Brooks |
| Nicholas Gonzalez | Detective Luke Morales |
| Jeremy Owens | Headless Horseman |
| Richard Cetrone | Headless Horseman (Weapons) |
| Craig Branham | Headless Horseman (Horseback) |
| Daniel J. Roberts | Tour Guide |
| Vince Pisani | Paul Short |
| Deja Dee | Desk Clerk |
| Allen O'Reilly | Samuel Adams |
| Paul Burke | Paul Revere |
| Rae Becka | Mom |
| Zach Shirey | Son |
| Erica Page | Chat Lady |
| Jeff Kidd | Dragoon Horseback soldier |
| Mary Austin | Diner Patron |
| Kristi Booher | Detective |
| DuRa Brown | FBI Agent |
| Brenda Moss-Clifton | Pedestrian |
| Alizdair Sebastien Ray | Kid in Crowd |
| Samuel Smith | Escort Driver |
| Joelle Vick | Detective |