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Halloween Happenings: The Full 2025 Rivertowns Schedule

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The scene from Tarrytown's Halloween Parade

October 3, 2025

In the month leading up to Halloween, there are dozens of events, activities, entertainment and downright scary stuff going on. To help readers decide where to go, The Hudson Independent offers a comprehensive calendar, starting this weekend:

SLEEPY HOLLOW

Oct. 4 Kids Pumpkin Painting, 11:00 a.m. Devries Park

Oct. 17 Halloween Block Party, 5:00 p.m. Beekman Avenue

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SLEEPY HOLLOW CEMETERY (sleepyhollowcemetery.org/special-events)

Oct. 5: Paint a Headless Horseman, 11:00 to 3:00 p.m.

Oct. 11: The Strange Case of Dr. Jekyll and Mr. Hide, 6:30 to 7:30 p.m. and again from 8:30 to 9:30 p.m.

Oct. 12: Bram Stoker’s Dracula, 6:30 to 7:30 p.m. and again from 8:30 to 9:30 p.m.

Oct. 28: The Man Behind the Legend Washington Irving, 8:00 to 9:00 p.m.

PHILIPSBURGH MANOR

(Ticket Info: www.hudsonvalley.org)

The Headless Horseman Files: An Immersive Sleepy Hollow Whodunit dates are: Oct. 3-5, 10-13, 17-19, 24-26, 31-Nov. 1.

Tickets are $30 for adults, $25 for children (3-17), and free for children 2 and under. Historic Hudson Valley members receive a 15% discount. On this 45-minute walk through the historic grounds of Sleepy Hollow’s Philipsburg Manor, visitors encounter suspicious townsfolk—each with their own tale and motive for causing the demise of Ichabod Crane. Visitors work together to mine the clues and decide who they think the Headless Horseman really is.

The Spirits of Sleepy Hollow Country: A Night of Legendary Magic dates are: Oct. 3-5, 10-13, 17-19, 24-26, 31-Nov. 1.

Tickets start at $65. Historic Hudson Valley members receive a 15% discount. Featuring nationally renowned illusionists Mark Clearview and Nick Wallace, this back-by-popular-demand event features these conjuring masters communicating with the spirits of Sleepy Hollow Country like Hulda, Major Andre, and the Headless Horseman, delighting and thrilling audiences, who have multiple chances to participate in the experience. The event takes place at Philipsburg Manor in the heart of Sleepy Hollow. Snacks and drinks, including local wine and beer, will be available to purchase. Premium tickets include a complimentary beverage and cabaret style seating.

Twilight Village at Sleepy Hollow dates are: Oct. 3-5, 10-13, 17-19, 24-26, 31-Nov. 1.

Tickets are $30 for adults, $25 for children (3-17), and free for children 2 and under. Historic Hudson Valley members receive a 15% discount on tickets. Twilight Village features traveling musicians and performers, a robust market with food, drink, and souvenirs, and plenty of photo-ops, including with the Headless Horseman.

Irving’s ‘Legenddates are: ’ Oct. 3-5, 10-13, 17-19, 24-26, 31-Nov. 1.

Tickets start at $45 for adults and $40 for children (3-17). Historic Hudson Valley members receive a 15% discount on tickets. Performing amid the lush landscape of Washington Irving’s estate, master storyteller Jonathan Kruk, accompanied by professional musician Jim Keyes, brings to life the story of The Legend of Sleepy Hollow in this outdoor, evening event, a perennial favorite. Snacks and drinks, including local wine and beer, will be available to purchase.

Headless Horseman display at The Great Jack O’Lantern Blaze.

VAN CORTLANDT MANOR (Croton-on-Hudson)

The Great Jack O’Lantern Blaze: Hudson Valley

Features illuminated, individually hand-carved jack o’ lanterns in elaborate, professionally lit displays throughout the historic landscape of Van Cortlandt Manor. The Gourd & Goblet Tavern is a sit-down VIP hospitality experience set in an 18th-century inn nestled along the pumpkin trail and requires a separate ticketed admission. It includes table service with delicious snacks, cocktails, and mocktails. The Tavern experience is recommended for ages 18+. The Headless Horseman’s Hideaway is a spirited stop on the pumpkin trail that includes a choice a small snack, cocktails, and mocktails. Photo-ops with the Headless Horseman are included in this separately ticketed VIP experience. Van Cortlandt Manor is at 525 South Riverside Avenue, just off Route 9 in Croton-on-Hudson.

TARRYTOWN

Oct. 4: Scarecrow Making, Parking Lot D 238 W. Main St. Session 1: 10:45 to 11:45 a.m.; Session 2: Noon to 1:00 p.m. Pre-registration required: https://tarrytown.recdesk.com/community/home

Oct. 14 Halloween Window Painting, 3:30 to 5:30 p.m. Paint will be provided by Tarrytown Recreation Dept. Register: https://tarrytown.recdesk.com/community/home

Oct. 17: Trunk or Treat, 4:30 to 6:30 p.m. Lot E Tarrytown Recreation Dept. Lot Best decorated car will win a prize!

Oct. 17 Movie Night, Pierson Park

To vote for spooky flick, visit: https://forms.gle/CP1iwieMLTHCB0919

Oct. 25: The 23^rd Annual Halloween Parade, starts at 5:00 p.m. Route: Patriots Park down Broadway to Main Street to Windle Park.; Entertainment, music, floats, etc.

IRVINGTON

Oct. 1-31: Trick or Triage is a month-long mission game, hosted by the Irvington Green Team, that offers challenge opportunities across Irvington. Each challenge earns points that contribute to a prize. All ages; free.

Oct. 1-31: The Octagon House’s Myths & Mysteries Tour unravels the mysteries behind this historic 1860 home, including the otherworldly experiences of its previous occupants. Ages 12 and up; $29-34.

Oct. 3-Nov. 1: Irving’s Legend Jonathan Kruk casts a spell with this dramatic telling of Washington Irving’s classic tale, “The Legend of Sleepy Hollow,” which features live music and sound effects by Jim Keyes, an appearance by the Headless Horseman, and a cast of shadowy characters. Washington Irving’s Sunnyside; Friday to Sunday, 6 pm, 7:30 pm, 9 pm; tickets start at $40.

Oct 4: Eric Walton: Mentalist & Magician Hailed by the New York Times as an “erudite magician and rabble rouser,” this award-winning and critically-acclaimed entertainer performs his singular brand of mentalism, mystifying feats of mind-reading, and magic. The Irvington Theater, ages 14 and up; $33. Use code MAGIC25 for 25% off.

Oct 9: Witch Please! This spooktacular drag performance stars fierce queens as your favorite Halloween icons, giving high-energy performances and an unmissable Sanderson Sisters finale. The Irvington Theater, 7:30 pm. Ages 21 and up; tickets from $33.

Oct 18: Harvest Hay Ride at Matthiessen Park includes horse and wagon rides, live music by Jake’s Rockin’ Country Band, and a bake sale hosted by the IHS Midnight Run Club. Matthiessen Park, 6:00-8:30 pm: Haunted hayrides begin at 7 p.m. Free.

Oct. 24: Haunt on the Hudson is a local festival featuring live entertainment, food trucks, family-friendly activities, Spookeasy with festive libations, costume contest for children and adults, and seasonal surprises throughout the night. Rain date: October 25th. (Hosted by The Lark Club and Symphony Medical). Matthiessen Park, 5-8 pm. Tickets are $15 for adults and $8 for kids (ages 2-13).

Oct. 25: Window Painting on Main Street: Middle Schoolers are invited to decorate the windows of participating local businesses. 10 am to 12 pm. Free.

Oct. 26: The Irvington Halloween Parade will kick off at the Immaculate Conception Church at 3:15 pm, and end at Main Street School. Live music by Cliff Mays Band and treat bags provided by the Irvington Fire Company. Free.

Oct. 31: Village Porchella: Local bands, including Evil Eckar, The Skam and Killer Mixtape, rock out on local porches in town for the annual town Halloween party. This year’s lineup includes 14 bands playing every half hour. 5 pm-10 pm. Free.

DOBBS FERRY

Oct. 18: The Children’s Village Masquerade Gala. A celebration of the 20th anniversary of their annual costume party, which benefits The Sanctuary, Westchester’s only shelter dedicated to teens experiencing homelessness, offering stability, support, and a path forward. Westchester Manor, Hastings. 7:00 p.m. Tickets starts at $115.

Oct. 30: Halloween Spectacular featuring Hocus Pocus Enjoy games, decorations, crafts, candy, and a screening of Hocus Pocus under the stars. Keeper’s House on the Old Croton Aqueduct. 5-8 pm; all ages.

Oct. 31: Springhurst Halloween Parade, Elementary school students show off their spooky (or goofy) costumes at this morning parade for parents. 9:30 am to 10:30 am.

Oct. 31: Halloween Storytime at the Keeper’s House Join Ms. Gina for a special Halloween storytime and craft activity. Keeper’s House on the Old Croton Aqueduct. 10:30 am; ages 2-4

Oct. 31: Trick or Treat at the Library: Little ones are invited to visit the library for candy, prizes, and crafts as part of Dobbs Ferry’s Downtown Trick-or-Treat Event. Dobbs Ferry Library, 4pm.

Oct. 31: Dobbs Ferry’s Downtown Trick or Treat Event. Don your costume and join the Dobbs Ferry community in town for this annual trick or treating tradition.

Thursday, Oct. 23 to Saturday, Oct. 25 Downtown Window Painting – a chance for kids and families to decorate downtown storefronts for Halloween. Register before noon October 20 at recreation@dobbferry.gov

Sunday, October 25 : 11:30 a.m.: Pet Parade near the flagpole at the Dobbs Ferry Waterfront, from noon to 4:00 pm: Halloween Bash, also at the Dobbs Ferry Riverfront Park, with inflatables, bubbles, food trucks, and more

Oct. 31 4:00 – 6:00 p.m: Trick or Treating in downtown Dobbs Ferry (Main and Cedar Streets) with music and merriment From 6:00 to 9:00 p.m: Halloween Block Party Main Street from Oak St. to Chestnut St., featuring an outdoor Halloween movie, glow-in-the-dark mini golf, cornhole, and other games.

Nov. 2 Pumpkin Smash at Gould Park
3:00 p.m: Annual post-Halloween bashing of the old pumpkins, accompanied by pumpkin-tossing competition

For more info and to register, contact the village: recreation@dobbsferry.gov

ARDSLEY

Oct. 18: (Unrelated to Halloween): A ribbon-cutting ceremony at Ardsley’s newly-renovated Pascone Park – 2:45 p.m.

3:00 p.m. to 7:00 p.m. celebration with balloons, bouncy castles, games, chess matches, food trucks. Fireworks at 7:00 p.m..

Ardsley kicks off its Halloween celebration on Friday, October 24 with a screening of “The Dog That Saved Halloween” at Pascone Park starting at 6:30-6:45 p.m. The next day the village hosts its annual Trunk & Treat event, also in Pascone Park. Children in costume assemble at the playground around 10:45 a.m. on Saturday, October 25 for a march to the middle school parking lot, escorted by a fire truck. There, 20 or so cars decked out for Halloween (including a police car and ambulance) pass out candy while a DJ spins Monster Mash and other Halloween classics.

HASTINGS

Hastings’ festivities begin a full two weeks before Halloween night. On October 18 from 9 am to 2 pm, there will be a downtown window-painting event. Families are invited to decorate storefront windows with Halloween-themed paintings. And for the first time, adults will get a piece of the action with a special category. Pre-registration is required.

Oct. 23, from 6:00 to 8:00 p.m, the Hastings Recreation Center is hosting a Family Pumpkin Carving event. The cost is $10.00 per family; pre-registration is required.

Oct. 23 Friday Night Spooktacular, from 6:00 p.m. to 8:00 p.m. on Warburton Avenue, features truck-or-treating*, music, food, a huge slide for kids and carnival games.

Those wishing to participate are urged to go to Hastings Recreation: Halloween Happenings 2025 for more details presented on a colorful poster.

*The Rec Department is soliciting candy for this event.

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