Nearly Two Dozen 2025 Halloween Events in Westchester

Halloween events in Westchester bring an extra spark to an already festive season. Alongside the many fall festivals and special movie screenings this month, these celebrations represent some of the best autumn traditions in the county. The Westchester Halloween lineup offers something for every type of reveler, from fan-favorite pumpkin illuminations and family crafts to interactive theater experiences and atmospheric tours of historic gothic estates. With so many ways to join in the fun, the county is brimming with can’t-miss events this October.

September 26 & 28
The Haunted Word: The Tales of Edgar Allan Poe
Presented by The Armonk Players
The Armonk Players stage a theatrical tribute to Edgar Allan Poe, weaving together dramatizations of his poems and short tales. This production dances between the macabre and the lyrical sides of Poe’s writing, offering an intimate look at his famed literary prowess. Staged at Whippoorwill Hall at the North Castle Public Library, the performance underscores the Armonk Players’s dedication to blending classic works with inventive staging.

Through November 8
Ghost Tours at Tarrytown Music Hall
Presented by Tarrytown Music Hall
Westchester adventurers who are not faint of heart can tour Tarrytown Music Hall (TMH) with a spooky spin. This fall, master storyteller Jonathan Kruk serves as guide to the Ghosts of The Music Hall, revealing the haunted history of one of the Hudson Valley’s oldest theaters. He’ll share stories of ghostly encounters and the building’s past, blending architectural history with local lore. The program appeals to both paranormal enthusiasts and those curious about the theater’s place in Westchester history.

Through November 24
The Great Jack O’Lantern Blaze
Presented by Historic Hudson Valley
The Great Jack O’Lantern Blaze, a seasonal favorite for families and Halloween enthusiasts alike, returns to Van Cortlandt Manor in Croton-on-Hudson, where more than 7,000 hand-carved pumpkins are illuminated through elaborate displays. New this year are a glowing pumpkin Ferris wheel, video game displays and a show-stopping Wizard of Oz-inspired installation.

Through November 30
Gothic Glenview Tours
Presented by Hudson River Museum
Hudson River Museum is getting guests into the spooky season with an after-hours tour of its 19th-century mansion Glenview. On this specialized tour, guides focus on the Gothic details of the building’s architecture and décor, highlighting how the house reflects Victorian tastes for the macabre. Candlelit halls and spooky ghost stories add magic and intrigue to this exploration of history and design.

October 3 – November 1
Twilight Village at Sleepy Hollow
Presented by Historic Hudson Valley
Philipsburg Manor transforms into a “Twilight Village,” where lantern-lit paths guide visitors through atmospheric vignettes inspired by folklore. Actors bring to life eerie tales and uncanny characters that blur the line between history and myth. With immersive sets and hauntingly beautiful staging, the event sets itself apart from bigger Halloween attractions. Instead, visitors are offered an intimate seasonal experience that feels far more personal.

October 3 – November 1
The Headless Horseman Files
Presented by Historic Hudson Valley
Step into the layers of lore behind Washington Irving’s most famous ghoul: the Headless Horseman. Blending archival documents, interactive exhibits and theatrical storytelling, this program at Philipsburg Manor investigates how a piece of early American fiction became a global legend. Visitors can see where history, myth and pop culture converge through Sleepy Hollow’s most enduring tale.

October 3 – November 1
Irving’s Legend
Presented by Historic Hudson Valley
Irving’s Legend, performed at Washington Irving’s Sunnyside estate, retells The Legend of Sleepy Hollow with a bit of theatrical flair. Actors, live music, and special effects breathe life and adventure into the cursed tale of Ichabod Crane and the Headless Horseman. The production celebrates the timeless appeal of Irving’s story while offering families a seasonal favorite steeped in local tradition.

October 3 – November 1
The Spirits of Sleepy Hollow Country
Presented by Historic Hudson Valley
Master storytellers gather at Philipsburg Manor to share chilling ghost tales rooted in Hudson Valley history. The program connects oral traditions with the region’s folklore, evoking spirits that are steeped in local Hudson Valley culture. Candlelit settings heighten the atmosphere, inviting audiences into an evening of spine-tingling narratives that have haunted the area for centuries.

October 3 – November 1
An Audience with Poe
Presented by Historic Hudson Valley
Enjoy an evening with Edgar Allan Poe from beyond the grave. Actor Campbell Harmon embodies the famed writer in a dramatic one-man show that explores the author’s life and works through readings of classic tales and poems. Audiences are invited to explore Poe’s dark imagination alongside his razor-sharp wit. Set in the Library at Historic Hudson Valley in Sleepy Hollow, the performance bridges literature and theater, conjuring the vision of a 19th-century world that shaped one of America’s most prized creators. Fridays through Sundays.

October 16-26
Peek-a-Boo
Presented by River’s Edge Theatre Company
Peek-a-Boo, an immersive production presented by River’s Edge Theatre Company and inspired by the hidden histories of the Hudson Valley, returns to the Bethany Arts Community. Set in a 1920s speak-easy, the show combines intimate encounters, haunting local legends and voyeuristic thrills. Audiences meet figures like Hulda the Witch and John André as history and fantasy intertwine in a torrid, local tale. An opening night party on October 16 includes cocktails, a vintage photo booth and tarot readings, adding to the atmospheric experience. Mature audiences only. Dates vary.

October 16-26
Lyndhurst After Dark
Presented by Lyndhurst Mansion
By lantern light, visitors explore Lyndhurst Mansion on a guided nighttime tour that reveals the estate’s mysterious corners and storied past as told by performers. The program highlights the architecture and decor of Lyndhurst, as well as special items on display for the spooky season, introducing superstitions of the time. Dates vary.

October 11
Halloween Cult Horror Double Feature: Mad Love & I Walked with a Zombie
Presented by New Rochelle Public Library
The New Rochelle Public Library Film Series enters the spooky season with a cult horror double feature. Audiences are invited to rediscover Mad Love (1935), starring Peter Lorre in his American film debut, and Jacques Tourneur’s atmospheric I Walked with a Zombie (1943). Together, these timeless classics drive nail-biting psychological suspense and gothic terror on screen. The program is free and open to the public, offering both cinephiles and curious newbies a chance to experience vintage horror together.

You may also enjoy: What’s Westchester Watching? October Edition

October 18
Sip and Create: Mask Making
Presented by ArtsWestchester
ArtsWestchester’s Sip and Create series invites adults to an evening of creativity and conversation. This month’s session takes on mask making. Participants will design and decorate unique wearable art, guided by professional teaching artists. Wine and refreshments set a relaxed Halloween-infused tone, making the program double as both a hands-on workshop and a fun social gathering.

October 15-25
Hulda’s Night
Presented by Rockefeller State Park Preserve
Healer and patriot Hulda’s story is interwoven with local Revolutionary War history. In this theater experience, guests will be transported back to the American Revolution during four acts, each at different locations along Rockefeller’s carriage roads. Through storytelling and performance, Hulda’s tale is brought to life against the evocative backdrop of Sleepy Hollow. The program offers a blend of history, a bit of folklore and plenty of seasonal atmosphere.

October 18 & 19
Trick-or-Treat Weekend at Lyndhurst
Presented by Lyndhurst Mansion
Children can do all of their trick-or-treating in one place at Lyndhurst Mansion this year. Kids in costume are invited to trick-or-treat through the Lyndhurst estate. Historic backdrops and festive decorations create a safe and memorable environment for families. The program adds a playful note to the mansion’s Halloween season, welcoming the youngest visitors into its Gothic halls.

October 18
Spooktacular Celebration
Presented by New Rochelle Public Library
Among the many attractions of ArtsFest 2025 will be a festive reopening of the New Rochelle Public Library’s Children’s Garden. The event pairs seasonal crafts and activities with a Halloween theme aimed at families. Besides the reintroduction of this garden space, storytelling, art creation and garden tours help to push creativity and community for all visitors.

Saturdays & Sundays in October
Family Art Workshop: Masquerade Masks
Presented by Hudson River Museum
Visitors to Hudson River Museum can make masks for the whole family this season as they are invited to design festive masquerade masks in this hands-on art workshop. Teaching artists guide participants in crafting colorful designs inspired by global traditions and practices. The program combines creativity with festive fun, encouraging children and parents to explore art-making together.

October 23
BYOB Nights: Kusama-Inspired Pumpkins
Presented by The Rye Arts Center
The Rye Arts Center hosts a Halloween craft inspired by art as guests will paint their own pumpkins using Yayoi Kusama’s works as inspiration. Kusama’s paintings feature colorful patterns, particularly polka dots. The event geared toward adults provides all needed art supplies, and is a “BYOB” (“bring your own bottle”) workshop.

October 25 & 26
Gothic Market Weekend
Presented by Lyndhurst Mansion
Guests can explore the grounds at Lyndhurst Mansion during its annual fall market weekend. Featuring artisan vendors, seasonal foods, visits from the Headless Horseman (10/25, 1-3pm), tarot readings and Victorian tintype photographs. Gothic-inspired décor sets the tone while families are invited to browse vendors that offer “mix of spooky oddities, curated antiques, gothic jewelry, and witchy wares.”

October 25
Halloween Movie Marathon IX
Presented by Jacob Burns Film Center
Jacob Burns Film Center continues its Halloween tradition with an all-day horror movie marathon. Now in its ninth year, the event curates a surprise lineup of cult favorites, classic thrillers and hidden gems, many of which are only revealed as the lights dim. Curated by film critic Monica Castillo, this year’s fun features seven titles, including favorites like A Nightmare on Elm Street 3: Dream Warriors and Donnie Darko, as well as rarities like Jess Franco’s Vampyros Lesbos and Ken Russell’s Altered States (both on 35mm). Doors open at 8pm for an 8:30pm kickoff, with additional surprise films revealed as the night unfolds.

You may also enjoy: What’s Westchester Watching? October Edition

October 25 & 26
Family Art Workshop: Jack-O’-Lantern Jars
Presented by Hudson River Museum
This workshop invites families to make glowing jack-o’-lantern jars using simple craft materials. Children, who are guided by the help of artists, decorate jars with expressive faces and seasonal motifs. The event emphasizes creativity and collaboration, offering an opportunity to take home a personal and handmade Halloween keepsake.

November 2
Oni Halloween Festival
Presented by Hammond Museum & Japanese Stroll Garden
The Hammond Museum blends autumn tradition with Japanese folklore during its annual Oni Halloween Festival. Inspired by the mischievous demons of legend, the event features live performances, seasonal food and hands-on family activities. Guests can wander the stroll garden at the peak of its fall splendor as they encounter cultural stories and rituals that cast Halloween in a new light. The festival offers an East-meets-West celebration of creativity, community and seasonal spirit.

You may also enjoy: Hammond’s Stroll Garden Offers Respite and Tranquility in Westchester

You May Also Enjoy:

• It’s Officially Fall Festival Season in Westchester!
• What’s Westchester Watching? October Edition
• Armonk Has Heart (and New Public Art)
• Performing Arts Center at Purchase Announces 2025-26 Lineup
• Dance Performances Take Center Stage in Westchester

_{Photos (top to bottom): Historic Hudson Valley’s Twilight Village, The Great Jack O’Lantern Blaze (both photos courtesy of Historic Hudson Valley, Blaze photo credit: Angie-Gaul); Hudson River Museum’s Gothic Glenview Tours (photo course: Hudson River Museum); River’s Edge’s Peek-a-Boo (photo source: River’s Edge); Lyndhurst’s Gothic Weekend (photo source: Lyndhurst Mansion)}