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Ultimate Guide to Halloween 2021 in Sleepy Hollow and the Rivertowns

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September 24, 2021

By Brianna Staudt —

Whether you’re a local anticipating a favorite Halloween tradition or a visitor looking to experience Halloween in Sleepy Hollow Country for the first time, The Hudson Independent has you covered. Read below for all the tricks, treats and haunts in Sleepy Hollow, Tarrytown, Irvington, Dobbs Ferry and the surrounding area.

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Please note this list will be updated as additional events are confirmed. Required pandemic precautions are included.

The Tarrytown Halloween Parade and block party have been cancelled.

Horseman’s Hollow, the Old Dutch Church Fest and Jay Ghoul’s House of Curiosities are also not running this year.

The Sleepy Hollow Tarrytown Chamber of Commerce is staffing its office at 1 Neperan Road in Tarrytown on Saturdays 9 a.m.–1 p.m. throughout the fall to help visitors navigate local businesses. Stop by for maps, recommendations and parking information.

TarryHollow Walking Tours
Tour #1 starts at 11 Dell Street/418 North Broadway
Sleepy Hollow
Sept. 5-Nov. 14, Saturdays and Sundays; 10 a.m., 12:30 p.m. 3 p.m.
$24.99/ticket
https://www.thehistoricalsociety.net/events/tours-tarryhollow/
Travel back in time with the Tarrytown and Sleepy Hollow historical society on a 1.5- or 2-hour tour of the area. The Hudson Independent recommends Tour #1: “TarryHollow: Irving, the Old Dutch Church and the Colonial Experience” for Halloween fun, though there are three popular tours available. Arrive 15 minutes early for check-in. Advance reservations required; purchase tickets online. Private tours available.

Evening Lantern Tour
Sleepy Hollow Cemetery North Gate
540 North Broadway
Sleepy Hollow
Friday and Saturday nights in September; every evening in October; weekends and select weekdays in November. Times vary.
$30
https://www.showclix.com/event/classic-evening-lantern-tour-2021
Explore the historic Sleepy Hollow Cemetery by the light of a kerosene lantern. This one-hour tour focuses on the north end; visit during the day to see Irving’s grave. Ages 10 and up.

The Great Jack O’Lantern Blaze
Van Cortlandt Manor
525 S. Riverside
Croton-on-Hudson
Sept. 17-Nov. 21, select nights
$24; members and children 2 and under are free
https://hudsonvalley.org/events/blaze/
Breath-taking display of over 7,000 jack-o’-lanterns, which are hand-carved and arranged on-site. New installations for 2021 include the New York City skyline and an “immersive” river display. Tickets must be purchased in advance.

Champagne Cocktails with the Dead
Sleepy Hollow Cemetery – North Gate
540 North Broadway
Sleepy Hollow
Sept. 26 and Oct. 3, 5-7:30 p.m.
$85
https://visitsleepyhollow.com/events/champagne-cocktails-with-the-dead/
Peak inside mausoleums and learn family histories, champagne cocktail and/or light refreshment in hand. No jeans or shorts, but comfortable walking shoes are recommended. For ages 21 and up; masks required in the mausoleums.

Fall Reflections: An Installation
Lyndhurst Mansion, Rockery Pathways
635 S. Broadway
Tarrytown
Sept. 30-Oct. 31, 9:30 a.m.-4:30 p.m.
Free with purchase of a grounds pass ($10; children 6 and under and Lyndhurst Members are free)
https://lyndhurst.org/events/outdoor-decor/
Discover witches and other spirits in the fall landscape south of the mansion. New for 2021: a special art installation from LiteMirror.

Evening Lantern Tour
Sleepy Hollow Cemetery North Gate
540 North Broadway
Sleepy Hollow
Friday and Saturday nights in September; every evening in October; weekends and select weekdays in November. Times vary.
$30
https://www.showclix.com/event/classic-evening-lantern-tour-2021
Explore the historic Sleepy Hollow Cemetery by the light of a kerosene lantern. This one-hour tour focuses on the north end; visit during the day to see Irving’s grave. Ages 10 and up.

Home of the “Legend”
Washington Irving’s Sunnyside
GPS address: 3 West Sunnyside Lane
Irvington
Oct. 1-Nov. 8, Fridays-Sundays and Columbus Day; entries 10 a.m. – 3:30 p.m.
$10-$12
https://hudsonvalley.org/events/home-of-the-legend/
Tour the first floor of Irving’s home and learn how “The Legend of Sleepy Hollow” has lived on in popular culture. Family friendly.

Irving’s “Legend”
Washington Irving’s Sunnyside
GPS address: 3 West Sunnyside Lane
Irvington
Fridays-Sundays Oct. 1-31, 6:30, 8 and 9:30 p.m.
$24-$35
https://hudsonvalley.org/events/irvings-legend/
Master storyteller Johnathan Kruk performs “The Legend of Sleepy Hollow.” Live music and an appearance by the Headless Horsemen himself. Tickets required and must be purchased online in advance. Appropriate for all ages.

“Myths and Mysteries” Tour 
The Armour-Stiner Octagon House
45 W. Clinton Ave.
Irvington
Oct. 1-31; multiple dates and times
$27-29
https://www.showclix.com/event/myths-mysteries
Explore this 1860 historic home with a one-hour tour featuring its “connection to the spiritual world,” including “unexplained and uncanny” events. Is there a resident ghost? Masks required; not suitable for individuals with mobility difficulties.

Pumpkin Painting and a Hayride
Devries Park
139 Devries Ave.
Sleepy Hollow
Oct. 2, 11 a.m.-12 p.m. or 12-1 p.m.
Free
Paint and decorate a pumpkin (pumpkin and supplies provided) and take a hay ride around the park. Presented by the Sleepy Hollow Department of Recreation. Email rpell@villageofsleepyhollow.org or adepaolo@villageofsleepyhollow.org to reserve your time slot. 100 children only per time slot.

Halloween: A Haunted History Virtual Presentation
Oct. 4, 7 p.m. over Zoom
Free
This new program traces the “strange history” of Halloween, from Old World festival to modern holiday. Presented by the Warner Library. Registration required.

Halloween Crafts
Warner Library
121 North Broadway
Tarrytown
Oct. 6, 4 p.m.
Free
Come to the children’s garden to make spooky — not scary — Halloween decorations using recycled materials. For ages 3 and up. Registration required and limited. Call the children’s desk.

Murder & Mayhem
Sleepy Hollow Cemetery North Gate
540 North Broadway
Sleepy Hollow
Thursdays, Oct. 7-Nov. 11; 7:30-9:30 p.m.
$45
https://www.showclix.com/event/murder-mayhem-2021
Two-hour, lantern-light walking tour of the cemetery’s darker history, including the scene of a grave robbery and victims of  the “Mad Murderer of Sleepy Hollow.” Ages 18 and up. Please note this event is an approximately 1.5-mile walking tour in the dark that includes steep hills and stairs.

Scarecrow Making
Parking Lot D (to the right of the recreation department)
238 W. Main St.
Tarrytown
Oct. 9, 10:45-11:45 a.m. or 12-1 p.m.
Free
Register by Oct. 7 at this link (space is limited): https://tarrytown.seamlessdocs.com/f/qyeh2no2hgky
Make a scarecrow to be displayed by the village along Main Street or Broadway. Straw, bags, ties and frames will be provided. Participants bring their own clothing, scissors and markers. Participants may also choose to pick up supplies, build their scarecrow at home, and drop it off by 1:30 p.m. Masks required.

Paint your own Witchy Wonderland
Washington Irving Memorial Chapel
540 North Broadway
Sleepy Hollow
Oct. 9, 12-3 p.m.
$65
https://www.showclix.com/event/paint-your-own-witchy-wonderland-2021
Join painter Heather Gleason to create your own Halloween canvas — paint, brushes, canvas and light refreshments included. Age 18 and up. This event takes place inside and requires masks regardless of vaccination status.

Halloween Slime
Warner Library
121 North Broadway
Tarrytown
Oct. 12, 4 p.m.
Free
Gather in the children’s garden to make a jar of Halloween slime. For grades 1-5. Registration is required and limited. Call the children’s desk.

Sleepy Hollow International Film Fest
Kingsland Point Park
Sleepy Hollow
Oct. 15-17; cars may arrive starting 5:30 p.m., first feature at 7:30 p.m.
$25/car each night
http://sleepyhollowfilmfest.com/horseless-carriage-cinema/
Outdoor double-features and food trucks. Movies include The Thing and Arachnophobia — see website or flyer for complete list of titles per night. Must purchase tickets in advance online and bring a printed copy. Audio available via radio; if you’re not planning to view the movie from inside your car, make sure you have a device that picks up FM radio.

Outdoor Screening of Hocus Pocus
Main Street School Lawn
101 Main Street
Irvington
Oct. 15; Doors open for “treats” and a red carpet at 5:30 p.m., movie starts at sunset
$5/ticket (must be purchased in advance via website)
https://www.irvingtontheater.com/hocuspocus
Presented by the Irvington Theater as part of its “Sunset Cinema” series. Attendees should bring blankets and chairs. Outside food is allowed, however, there is no alcohol allowed on school grounds. Don’t forget your costume!

2nd Annual SUP Witch Paddle
Horan’s Landing
57 River Street
Sleepy Hollow
Oct. 16, 4:30-6:30 p.m.
Free if you own your own SUP board or kayak; $35 to rent equipment
https://rivertownssupyoga.com/sup-witches-2021-2
Costume Required. Come to Horan’s Landing to hear a telling of the Legend of Sleepy Hollow. Then, launch with other witches at 5 p.m. on an evening paddle along the Sleepy Hollow Hudson River shoreline. Spectators welcome; the RiverWalk is a prime location to view the paddle. See the Wishing Wall while you’re there.

Mary Shelley’s Frankenstein
Washington Irving Memorial Chapel
540 North Broadway
Sleepy Hollow
Oct. 16, 5:30-7 or 8-9:30
$25
https://www.showclix.com/event/mary-shelley-s-frankenstein-2021EttIsCo
Enjoy an adapted presentation of this classic tale. Event is seated indoors; masks required regardless of vaccination status.

“Trunk-or-Treat”
Lot F (parking lot between the boat club and Losee Park)
Green Street
Tarrytown
Oct. 17, 4:30-6:30 p.m.
Free
Drive-thru format: families drive through the lot to view the decorated trunks and pick up treats along the way. Register your decorated vehicle to distribute candy on the Tarrytown Recreation website by Oct. 14. Contest for best vehicle. Presented by the Tarrytown Recreation Department.

Harvest Hayride
Matthiessen Park
1 Bridge St.
Irvington
Oct. 17; family rides 6-7 p.m., haunted rides 7-8:30 p.m.
Free
Come for a horse-and-wagon ride, refreshments and music by the Blu Road Orchestra Band. Masks must be worn while waiting online. No dogs. No pre-registration required. Presented by the Irvington Recreation Department.

Halloween Window Painting
Main Street and Broadway
Tarrytown
Oct. 20, 3:30-5:30 p.m.
Free
https://www.sleepyhollowtarrytownchamber.com/event-details/tarrytown-halloween-window-art-1
Help paint store windows on Main Street and Broadway! Children pickup paint in front of CVS on North Broadway between 3:30-4:30 p.m. Reserve your window at the link above — registration required. Parent/guardian supervision, masks and social distancing required. Presented by the Tarrytown Recreation Department.

Halloween Party
Warner Library
121 North Broadway
Tarrytown
Oct. 21, 4 p.m.
Free
Gather on the front lawn in costume for a story, treats and crafts. Ages 3 and up.

Halloween Terrariums
Irvington Library
12 S. Astor St.
Irvington
Oct. 21, 5:30-6:30 p.m.
Free
Make something fun (and a little spooky) for Halloween. In the program room; masks required. For grades 6-12. Registration required.

Pumpkin Painting for Teens/Pre-Teens
Dobbs Ferry Library Terrace
55 Main St.
Dobbs Ferry
Oct. 22, 4:30-6 p.m.
Free
Paint a miniature pumpkin outside on the terrace. Light food and beverages provided. E-mail amanning@wlsmail.org to register.

Sleepy Hollow Block Party
Beekman Avenue
Sleepy Hollow
Oct. 22-23, starting 5 p.m.
Free
Vendors, music and more

Haunted Hayride
Sleepy Hollow Village Hall/Firehouse
28 Beekman Ave.
Sleepy Hollow
Oct. 22-23, 7 p.m. – 12 a.m.

$40/ticket; $20 rate for Public Schools of the Tarrytowns students if tickets purchased at Village Hall before noon Oct. 22 with student ID.
https://sleepyhollowny.ticketleap.com/2021-sleepy-hollow-ny-haunted-hayride/
Face masks required. This event is not recommended for some children due to graphic content. Tickets required and must be purchased online in advance. Act fast — tickets sell out!

Sleepy Hollow Halloween 10K & Kids Fun Run
W. L. Morse School
30 Pocantico St.
Sleepy Hollow
Oct. 23, 10K 9:30 a.m.; Fun Run 9 a.m.
$40 registration through Oct. 17; $50 registration on race day. $5 for Fun Run.
http://www.rivertownrunners.org/sleepy-hollow-10k/
This 10K winds through historic Sleepy Hollow with sites including the Sleepy Hollow Cemetery, the Old Dutch Church, the Headless Horseman Bridge and a beautiful stretch along the Hudson River. Registration capped at 1,500 runners. Mile-long Kids Fun Run is for ages 6 and older includes a finisher medal. Costumes encouraged for runners of all ages but not required. Live music, and beer tasting for runners age 21 and older. Please note no strollers, inline skates or pets are allowed.

Outdoor Halloween Movie Night: Hotel Transylvania
Pierson Park
238 W. Main St.
Tarrytown
Oct. 23, movie starts at 6:30 p.m.
Free
Popcorn will be served. Bring blankets and chairs. Attendees are encouraged to support local restaurants and bring meals and snacks to the movie. Presented by the Tarrytown Recreation Department. No tickets or registration required.

Ghost Tours of the Music Hall
Tarrytown Music Hall
13 Main Street
Tarrytown
Daytime tours Oct. 24; late afternoon and evening tours Oct. 27-28
$25
https://tickets.tarrytownmusichall.org/eventperformances.asp?evt=2508
“Balcony to backstage” guided ghost tour of the 136-year-old theater. Vaccinated patrons only. Masks required. Flashlights provided for all attendees courtesy of Key Bank. Please note the tour requires stair climbing and standing for extended periods.

Downtown Halloween Window Painting Contest
Cedar and Main Streets
Dobbs Ferry
Oct. 24, 10 a.m.-2 p.m.
$5/individual (2nd-8th grades); $7/team (2 people 2nd-8th grades); $10/family (up to five immediate family members)
www.dobbsferry.activityreg.com
Decorate storefront windows as individuals, teams or families to compete for best in division or three overall prizes: “Most Original,” “Most Whimsical” and “Best Halloween Concept.” Presented by the Dobbs Ferry Recreation Department. Open to Dobbs Ferry residents and Dobbs Ferry school district students only. Must register by noon on Oct. 22. See link above for registration and official contest rules.

Halloween Origami
Dobbs Ferry Library
55 Main St.
Dobbs Ferry
Oct. 25-31
Free
Stop by the children’s room and check out a special Halloween origami station — fold paper bats, ghost and black cats! Ages 7 and up.

Halloween Story-Time
Irvington Library
12 S. Astor St.
Irvington
Oct. 26, 4-4:45 p.m.
Free
Come in costume for a story and a treat! In the library garden. Registration required. For ages 4 and up.

Hulda’s Night
Rockefeller Park Preserve
25 Sleepy Hollow Road
Sleepy Hollow
Oct. 27-30; 6 and 7 p.m. programs
$28
https://www.friendsrock.org/huldas-night
Guided tour through the dark woods to Hulda’s home, where she will tell her story. You’ll meet “The Leatherman” along the way — maybe some other friends, too. Bring a flashlight. No children under 10.

Irving’s Nightmare Presents: The Spider Lab
26 Irving Ave.
Tarrytown
Oct. 27-31; 6-10 p.m.
Free
https://www.facebook.com/IrvingsNightmare/
Elaborate local “yard haunt” that never disappoints.

Riverside Haunts
The Good Witch Coffee Bar
134 Southside Ave.
Hastings-on-Hudson
Oct. 28-29, 7 p.m.
$25
https://www.eventbrite.com/e/riverside-haunts-scary-stories-to-tell-by-the-hudson-tickets-166176336897
River’s Edge Theater Company hosts two nights of scary storytelling, history and live music outdoors. Recommended for mature audiences only. 10 percent of ticket sales benefit Riverkeeper.

Field of Screams
Memorial Park
103-105 Palisade Street
Dobbs Ferry
Oct. 29, 7-9 p.m.
Free
Can you make it from the baseball field to the playground without being scared? Geared toward children age 8 and up. Presented by the Dobbs Ferry Recreation Department.

Halloween in the Children’s Room
Dobbs Ferry Library
55 Main St.
Dobbs Ferry
Oct. 29-31
Free
Come in costume and pick out a prize! Ages 0-12.

Halloween at Kingsland Point Park
Kingsland Point Park
Sleepy Hollow
Oct. 30, 11 a.m.–5 p.m.
Free
Halloween crafts and treats in the park pavilion, 11 a.m.–1 p.m.; Halloween photo booth in Kathryn Davis Pavilion, 12–3 p.m.; “Howl-O-Ween” kids and pet costume parade starting at Kathryn Davis, 2–3 p.m.; “Truck-or-Treat” on the park field, 3–5 p.m. Kids of all ages welcome. No pre-registration required. Ice cream truck will be on-site for sales. Presented by the Sleepy Hollow Recreation Department.

Outdoor Movie Night: The Addams Family
Dobbs Ferry Waterfront Park
87 Ogden Park
Dobbs Ferry
Oct. 30, 6 p.m.
Free
Bring blankets and chairs. Refreshments for sale. Presented by the Dobbs Ferry Recreation Department. No tickets or registration required.

Pet Parade
Dobbs Ferry Waterfront Park
87 Ogden Park
Dobbs Ferry
Oct. 31, 11:30 a.m.
Free
Dress up your pet and meet at the flagpole for a loop around the park to show off their costumes. Dogs must be leashed. Masks recommend for unvaccinated individuals. Presented by the Dobbs Ferry Recreation Department.

Howl-O-Ween Bash
Dobbs Ferry Waterfront Park
87 Ogden Park
Dobbs Ferry
Oct. 31, 12-4 p.m.
Free
Inflatables, a petting zoo, mini-golf, food trucks and live music by Al Indig & Friends and Marguerite & co. Masks recommend for unvaccinated individuals. Presented by the Dobbs Ferry Recreation Department.

Downtown Trick-or-Treating
Cedar and Main Streets
Dobbs Ferry
Oct. 31, 4-6 p.m.
Free
Music by Rooney Tunes. Masks recommend for unvaccinated individuals.

Halloween Bands
Downtown Irvington
Irvington
Oct. 31 evening
Free
Check out local musical talent perform crowd favorites live in costume on front porches. This much-anticipated event is an annual tradition. Here’s the current lineup: Wild Thyme, Barn Owls, North Dutcher All-Stars, and Evil Eckar w/Death Island and the Dirty Irv Horns. Expect at least one other band on the 31st.

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