Where to go, what’s new, and how to keep up with Tarrytown and Sleepy Hollow events.
For months, the villages of Tarrytown and Sleepy Hollow have been planning and preparing a full calendar of events for residents and visitors of all ages to enjoy this Halloween season. Whether you’re a first-time or repeat reveler or just want to know where the traffic is heading, here’s a list of what’s happening this month in each village.
We’ll also point out what’s new this year, we’ll check in on what a few of our neighboring communities are doing for Halloween and then offer some suggestions for how to keep on top of all village events in the months ahead.
SLEEPY HOLLOW
BLOCK PARTY
Beekman Avenue
Friday, October 17; 5PM-11PM Saturday, October 18; 5PM-11PM
Free
Enjoy live music, entertainment, family activities, and vendors. If you have tickets to the Haunted Hayride, join the Party before and after.
New this year: Two popular local bands will be joining in for the first time to add to the musical entertainment.
For details: https://www.sleepyhollowny.gov
HAUNTED HAYRIDE
Sleepy Hollow Village Hall
28 Beekman Avenue
Friday, October 17 7PM -11PM Saturday, October 18 7PM – PM
Tickets are sold out for the general public, but students of the Tarrytown Union Free School District can go to the Village Hall with student ID from Mon-Fri 9AM-4PM until 10/17 at 12Noon.
The haunted hay wagon travels through Sleepy Hollow village and past the Old Dutch Church following Ichabod Crane’s flight from the Headless Horseman. Next: iron gates, dark woods, and clatters across a wooden bridge. Listen for the sound of hoofbeats!
For details: visitsleepyhollow.com/plan/sleepy-hauntedhayride/
SLEEPY HOLLOW CEMETERY TOURS
“The Original Knickerbocker: Washington Irving and ‘The Legend of Sleepy Hollow’”
Sleepy Hollow Cemetery South Gate
430 North Broadway
Saturdays and Sundays, 11AM-12Noon, 1PM-2PM through Thanksgiving weekend.
Meet the father of the American short story and learn all about Washington Irving (who is buried in the cemetery), his impact on American literature, and the enduring appeal of “The Legend of Sleepy Hollow,” especially popular during the Halloween season. In the story, the Headless Horseman is reported to ride swiftly through Sleepy Hollow at night as if reenacting the battle that took his head, before returning at daybreak to the churchyard where he is buried.
New this year: “The Strange Case of Dr. Jekyll and Mr. Hyde” An indoor, seated live performance.
Saturday, October 11 6:30PM and 8:30PM
Storyteller David Neilsen brings the classic tale of good vs. evil to life in an unforgettable dramatic reading of one of gothic horror’s true masterpieces.
For details and event tickets: https://www.sleepyhollowcemetery.org
Philipsburg Manor
381 N. Broadway
Twilight Village
Fridays – Sundays; October 3 – November 1
6PM-9PM Timed admissions
An immersive outdoor experience with live storytellers, fire performers, eerie encounters, a pop- up market, food trucks, cocktails, music, fortune tellers. Mingle with Legends icons Ichabod Crane and Katrina Van Tassel. Watch for a dramatic sound and light appearance by the Headless Horseman.
Headless Horseman Files
Fridays-Sundays; October 3 – November 1
Fridays 12PM-4:15PM Saturdays-Mondays: 11AM – 4:15PM
Appropriate for ages 8+.
Take a mysterious 45-minute interactive theatrical journey as you walk through the historic grounds and into a chilling live-action 18th-century whodunit. Piece together clues to decide what really happened to Ichabod Crane.
Spirits of Sleepy Hollow Country
October 3 – November 1
Fridays-Saturdays: 2PM, 6PM, 7:30PM, 9PM; Sundays-Mondays: 3:30PM, 5PM, 6:30PM
Ideal for ages 10+
Master illusionists Mark Clearview and Nick Wallace take you on a journey into the realm of the unknown at this spooky supernatural spectacle as they communicate with the spirits of Major Andre and the Headless Horseman,
New this year: Premium seats include a complimentary cocktail/mocktail.
For details and event tickets: https://www.hudsonvalley.org
Historic Hudson Valley
639 Bedford Road
Library
New this year “Audience with Poe”
Weekends October 3 – Nov 1 Recommended for ages 14+
Fridays: 5PM, 7PM, 9PM Saturdays: 2:30PM, 4:30PM, 7PM, 9PM Sundays-Mondays: 3PM, 5PM, 7PM
Sip, savor, and shiver with Poe’s darkest tales (The Raven, The Tell-Tale Heart, The Black Cat, The Masque of the Red Death) brought to life through storytelling, cocktails, and confections.
For details and event tickets: https://www.hudsonvalley.org
TARRYTOWN
Tarrytown Halloween Parade
Saturday, October 25 5PM
Route 9/Broadway, Patriots Park
Free
The 23rd Annual Tarrytown Halloween Parade heads south from Patriots Park along Broadway to Main Street, culminating in a Block Party with DJs, live music and performers, outdoor dining, and more. Register to participate in the parade as a theme or float. Prizes will be awarded.
For details or to register: https://www.tarrytownhalloweenparade.com
Tarrytown Music Hall
13 Main Street
Ghost Tours of the Music Hall
Assorted weekdays and Saturdays in October
Travel back in time with Master Storyteller Jonathan Kruk as he shares the historic lore and spirits that linger at the Tarrytown Music Hall which has hosted the Rockefellers, Goulds, and Vanderbilts at lavish balls, flower shows, and concerts. The Music Hall has also been the setting for President’s speeches, women’s suffrage rallies, endured several wars, depressions and pandemics including those of 1918 and 2019. Many people pass through – and some don’t leave! The building is an official site of the Haunted History Trail of New York.
“The Birds” (Film)
Sunday, October 5 7:30PM
Alfred Hitchcock’s famous horror-thriller featuring crows, gulls, and sparrows attacking the residents of a small coastal town. (Thanks to a group of volunteers, movies were brought back to the Music Hall in 2004.)
“Dracula” (Live performance by Theatre on the Road)
October 13 5pm
Appropriate for ages 12 and up.
Set in the shadowy countryside of 1920s England, this production brings to life the original Broadway script based on Bram Stoker’s iconic novel and made famous by Bela Lagosi on film and revived in 1977 with Frank Langella. This thrilling version blends horror, romance, and psychological drama.
Spooky (but not too scary) Stories
Saturday, October 18 1PM
Legendary Storyteller Jonathan Kruk creates frightful fun with tales of the Witch’s Surprise, Rolly-Head, the Haunted Hand, and live eerie music.
“Psycho” (Film)
Saturday, October 24 1PM and 7:30PM
Another Hitchcock classic, this 1960 horror film brings together an embezzler on the run, a shy motel proprietor, his disturbed mother, and a private investigator.
“The Rocky Horror Picture Show” (Film)
Sunday, October 25 9PM
Celebrating its 50th anniversary this year, this cult classic will be shown after the Tarrytown Halloween Parade and include a live shadow cast.
“Tarrytown – the Musical” (Live performance)
October 30 7PM
A hauntingly beautiful new musical based on Washington Irving’s Legend of Sleepy Hollow, will be presented on Halloween Eve, steps away from where the story first unfolded. Written and composed by Broadway’s Adam Wachter, the musical features Broadway and television favorites Krysta Rodriguez (The Addams Family, First Date, Smash), Andy Mientus (Les Miserables, Spring Awakening, The Flash), a surprise guest, and a Broadway band.
New this year: “Ride the Cyclone”(Live performance)
An all-teen cast from the Music Hall Academy will perform, sing, dance, and handle some of the backstage tech in this musical.
Dates to be announced.
New this year: the Music Hall has a new beverage called Rock the Hall by Soul Brewing company in Pleasantville.
For details and event tickets: https://www.tickets.tarrytownmusichall.org/
Lyndhurst Mansion
635 South Broadway
“Lyndhurst after Dark”
October 19-22 and 26-29
6-10 PM. Timed tickets. Appropriate for children aged 10 and older.
This nighttime tour provides a special opportunity to experience the mansion as it is decorated in the spirit of the season and to see rarely exhibited items from Lyndhurst’s collections that highlight mourning practices and the occult. A mixture of interesting new collection objects will join the old favorites on display, such as the mansion’s crystal ball and mourning portraits. Refreshments will be available for purchase.
“Roam on Your Own Weekend”
Saturday, October 18; Sunday, October 19
10AM-4PM Timed entry.
Appropriate for all ages.
Guests can wander the Mansion at their own pace enjoying the majestic vestibule, entrance hall, parlor, Victorian dining room, and art gallery decorated with autumnal trimmings for the season. Jimmy’s food truck will be onsite serving cider and donuts.
New this year: Kids can trick or treat throughout the Mansion. Wear a costume, bring a trick-or-treat bag, and roam for treats. Guides will be handing out little toys, tattoos, or games to children (only) in six of the rooms. Candy will be given out at the exit.
Also new this year: “Harvest Tea and Tour” on Sunday, October 5th. Guests will take a tour, then learn about Lyndhurst’s apple orchards while enjoying fine teas and scones with clotted cream and locally produced apple jam.
For details and event tickets: https://www.lyndhurst.org
If you feel like venturing a little north, south, or east of the Villages, here’s just a sampling of what our neighbors are doing this Halloween.
In Irvington, you can visit Sunnyside (Washington Irving’s Estate) Fridays through Sundays through October 31 for “Irving’s “Legend, an outdoor performance of the Legend of Sleepy Hollow with master storyteller Jonathan Kruk and his crew of creepy characters. The Octagon House in Irvington is offering “The Lady in White Immersive Ghost Story” October 2 – 18 and “’Tis the Wind and Nothing More” immersive tour October 23-November 1. Travel up to Croton-on-Hudson to see the Great Jack O’Lantern Blaze at Van Cortland Manor through November 16 where 7,000 carved pumpkins form animated displays. Hop over to the Jacob Burns Film Center for a Halloween Movie Marathon on Saturday, October 25. Or join the Halloween Howl sunset hike at the Wolf Conservation Center in South Salem on Saturday, October 25 from 5PM-6:30PM. Pre-registration is required. Bring flashlights and costumes are encouraged.
To keep up-to-date on all goings-on in Tarrytown and Sleepy Hollow in the months ahead, check out the following websites that offer free informative newsletters that cover events, construction, filming, traffic alerts and other activities impacting the villages.
Sleepy Hollow residents:
https://www.sleepyhollowny.gov; https://www.mtpleasantny.gov
Tarrytown residents:
https://www.tarrytownny.gov ; https://www.greenburghny.gov
The information in this article was compiled with the help of the representatives of the organizations mentioned above. Many thanks to them for their generosity and enthusiasm. Every effort was made to be exact, but things can change, tickets can be sold out, performances can be added to the schedule. To be current on all details related to an event that you want to attend, check the event website for ticket prices, any advisories, instructions, directions, etc. Wishing everyone a happy, fun, and safe Halloween season!
