23 open roles
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- Cider PresserVan Tassel Pumpkin Patch & Cider Press · Sleepy Hollow, NY (the cider press) · September 28, 1799
- WheelwrightSleepy Hollow Smithy · Sleepy Hollow, NY · September 22, 1799
- FarrierSleepy Hollow Smithy · Sleepy Hollow, NY (smithy + farm calls) · September 19, 1799
- BlacksmithSleepy Hollow Smithy · Sleepy Hollow, NY · September 16, 1799
- Hedger & DitcherHans Van Ripper Homestead · Sleepy Hollow, NY (the upland fields) · September 13, 1799
- PloughmanHans Van Ripper Homestead · Sleepy Hollow, NY (the upland fields) · September 10, 1799
- PeddlerTarry Town General Store · Distributed · September 7, 1799
- ShopkeeperTarry Town General Store · Tarry Town, NY · September 1, 1799
- MillwrightSleepy Hollow Grist Mill · Sleepy Hollow, NY (the millpond) · August 20, 1799
- Miller's ApprenticeSleepy Hollow Grist Mill · Sleepy Hollow, NY (the millpond) · August 17, 1799
- Master MillerSleepy Hollow Grist Mill · Sleepy Hollow, NY (the millpond) · August 14, 1799
- Bell-RingerOld Dutch Church of Sleepy Hollow · Sleepy Hollow, NY · August 11, 1799
- Church ChoristerOld Dutch Church of Sleepy Hollow · Sleepy Hollow, NY · August 8, 1799
- Sexton & GravediggerOld Dutch Church of Sleepy Hollow · Sleepy Hollow, NY (the burying-ground) · August 5, 1799
- Ostler / Stable HandThe Headless Horseman Tavern · Sleepy Hollow, NY (the post-road) · July 30, 1799
- Tavern CookThe Headless Horseman Tavern · Sleepy Hollow, NY (the post-road) · July 27, 1799
- InnkeeperThe Headless Horseman Tavern · Sleepy Hollow, NY (the post-road) · July 24, 1799
- Goose & Poultry KeeperVan Tassel Farm · Sleepy Hollow, NY · July 21, 1799
- DairymaidVan Tassel Farm · Sleepy Hollow, NY · July 15, 1799
- Head FarmhandVan Tassel Farm · Sleepy Hollow, NY · July 12, 1799
- Schoolhouse UsherSleepy Hollow Schoolhouse · Sleepy Hollow, NY · July 9, 1799
- Country SchoolmasterSleepy Hollow Schoolhouse · Sleepy Hollow, NY · July 3, 1799
- Horseman (headless)The Hollow Watch · Sleepy Hollow, NY · October 31, 1791