2025 Event Description
The Headless Horseman Rides Again Saturday, September 27 and October 4th!! We encourage everyone to dress in period costumes. Why? For the fun of it!!!
And, come in costume and get a free haunted hayride. If one of our staff likes your costume, they will give you a wristband for a free hayride!
**There are two performances in 2025. September 27 and October 4. Please plan to arrive at the winery by 5:30pm each day to ensure you see all of the performances and the Headless Horseman ride. Due to weather conditions on that day, the times are approximate because the performances must be concluded before dark.
Relive the Legend of Sleepy Hollow with townspeople Katrina, Brohm Bones, and of course the famous horse ride between Ichabod Crane and the Headless Horseman!
New in 2025,
* Bring a carved pumpkin and get a picture op with the headless horseman. Then leave the pumpkin to enhance the atmosphere of Eagle Hollow.
* Mummy Wrap Contest.
Limited to 5 teams.
Teams consist of 5 teammates or less.
7 minute time limit to complete your Mummy wrap.
The winning team gets front row seats to performances of the Witches, the School House, and the Headless Horseman Chase.
You must signup for the Mummy Wrap Contest at Greene Eagle Winery. The first 5 that signup get the opportunity to participate.
The Schoolmaster, Ichabod Crane and his students will perform a schoolhouse scene with special guest, the valley's own Len Rome from Ch 33 WYTV as Ichabod Crane, the Schoolmaster.
The three witches will perform a scene from William Shakespeare's play Macbeth.
**The Eagle Hollow Haunted Hayride will give you a fun, chilling experience! (additional fee of $3 per person or $6 for all day ride, per person)
**Our Shop in the Hollow returns this year starting at 3pm. Vendors will be showcasing their talents and offering various crafts for sale.
**OTHER IMPORTANT INFORMATION**
* * Entrance fee is $7 per person. Children 7 and under are free.
(we will hand out wrist bands to those who plan on leaving and coming back the same day to the event. Ask when you pay your entrance fee.) *A portion of each vehicle entrance fee will be donated to Maplewood High School Music Boosters.
**Bring your own chair or blankets
*Food Trucks will be on site & the winery will offer a special limited food menu.
*NO coolers or other beverages & food permitted on premises.
*Plastic Cups will be used for wine and beer. If you prefer a glass-glass, please bring it with you, or you can purchase one.
*NO wine or beer samples/tastings and no reservations are taken for this event.
Scheduled activities for 9/27/25 & 10/4/25
2025 Schedule of events
3:00-7:00ish- Shop in the Hollow (some vendors may stay later)
4:00- Trebuchet Firing, Hayrides Begin
5:00 Carved pumpkin pictures with the Headless Horseman
6:00 Mummy Wrap Contest
6:30 Vignette, the Three Witches
6:45 The Legend of Sleepy Hollow
Zombie Zoo dance
Haunted Hayrides continues
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