Spooky Spotlight: Sleepy Hollow


sleepy hallow“Certain it is, the place still continues under the sway of some witching power, that holds a spell over the minds of the good people, causing them to walk in a continual reverie. They are given to all kinds of marvelous beliefs, are subject to trances and visions, and frequently see strange sights, and hear music and voices in the air”― Washington Irving, The Legend of Sleepy Hollow

The perks of being Westchester residents are plentiful, but they seem to be amplified this time of year. With beautiful fall foliage, historic landmarks galore, and of course, legends. There’s no shortage of Halloween activities, but Sleepy Hollow seems to have everyone beat. Here’s our round-up of fun, fall happenings, or “Sleepy Things To Do” this Halloween.

Family Friendly

The Great Jack O’Lantern Blaze through November 21   

This fall, thousands of hand-carved pumpkins will illuminate the Van Cortlandt Manor. Find larger-than-life, spectacular outdoor displays, complete with synchronized lighting and an original soundtrack. See why visitors say there is no other experience like this in the United States! This year’s additions are the Blazin’ River, an immersive light installation with sea life, and the NYC Streetscape featuring the subway and iconic buildings.

More information and tickets can be found at pumpkinblaze.org Van Cortlandt Manor, 525 S Riverside Avenue, Croton-On-Hudson, NY 10520.

Home of the Legend: Now through November 8, Fridays-Sundays and Columbus Day; 10:00 a.m. – 3:30 p.m.

At this family-friendly happening, visitors can tour the first floor of Washington Irving’s house and watch an original shadow puppet short film. A special exhibit highlights how the Legend has lived in the imagination of popular culture through the centuries since its publication.

More information and tickets can be found at https://visitsleepyhollow.com/events Sunnyside, 3 W Sunnyside Lane, Irvington, NY 10533.

Sleepy Hollow Block Party: Friday & Saturday, October 22-23; 7:00 p.m. – 11:00 p.m.

A free block party on Beekman Avenue Friday and Saturday night. It is bustling with live music, children’s activities, and vendors.

Thrill Seekers

Murder Mystery at Sleepy Hollow Cemetery: Saturday, October 2; 7:00 p.m. – 9:30 p.m.

Somebody’s dead at Sleepy Hollow Cemetery (actually, many people are dead – it is a cemetery), and it’s up to YOU to bring the killer to justice! Everyone who attends is a suspect–even you! All attendees will receive a unique identity ahead of time (in case anyone wants to wear a costume), complete with secrets and clues, individual goals to achieve, multiple scandalous plots to unravel, and the chance to unmask the killer in your midst!

Buy tickets on http://sleepyhollowcemetery.org/special-events Sleepy Hollow Cemetery North Gate, 540 North Broadway, Sleepy Hollow, NY 10591.

Champagne Cocktails with the Dead: Sunday, October 3; 5:00 p.m. – 7:30 p.m.

Leave the kids at home, summon all your witches, and enjoy champagne cocktails and light refreshments as you peek inside some of the most beautiful mausoleums in Sleepy Hollow Cemetery! Learn the remarkable history of the families they were built for, revel in the beauty of their design and decoration, and help preserve this special place for generations to come with your attendance.

Only a limited number of tickets will be sold for this unique event. Buy tickets on http://sleepyhollowcemetery.org/special-events Sleepy Hollow Cemetery.

Haunted Hayride: Friday & Saturday, October 22-23; 7:00 p.m. – 11:00 p.m.

Climb aboard Sleepy Hollow’s annual Haunted Hayride and hold on to your head! All seems well when you board your hay wagon in the brightly lit streets of downtown Sleepy Hollow. Rumbling off into the dark, you realize too late you are heading down the Albany Post Road past the Old Dutch Church, following exactly Ichabod Crane’s flight from the Headless Horseman. Then you’re through a set of iron gates, and the wagon slips into the dark woods of the hollow. Clattering across a wooden bridge, you start to hear shrieks and the sound of hoofbeats… There’s a free block party on Beekman Avenue both nights to keep you entertained before your hair-raising ride through the real Sleepy Hollow. If you keep your head, you’re welcome to come back for more live music, children’s activities, and vendors.

Ticket sales are online only through the village’s website www.sleepyhollowny.gov. Park at the Sleepy Hollow High School/Middle School at 210 N. Broadway, Sleepy Hollow, NY, and walk to 28 Beekman Avenue.

Craft Fairs & Farmer’s Markets

Fall 2021 Westchester Craft Crawl: Sunday, October 3; 11:00 a.m. -5:00 p.m.

A free outdoor tour features 30 regional professional craft artists. The Crawl covers eight studio stops between Tarrytown, Ossining, and Cortlandt Manor, with each stop hosting 3–5 artists working in clay, wood, fiber, metal, jewelry, and mixed media.

For more information, visit https://www.westchestercraftcrawl.com/ Tarrytown – Makers Central, 84 Central Ave. Ossining & Cortlandt Manor (locations TBD)

Sleepy Hollow Cultural Festival: Saturday, October 2; 12:00 p.m. 

A celebration of the many cultures represented in Sleepy Hollow, including performances of traditional dance, live music, food, and a community art exhibition.

Kingsland Point Park, 299 Palmer Avenue, Sleepy Hollow, NY 10591.

Sleepy Hollow Craft & Street Fair: Sunday, October 10; 10:00 a.m. – 5:00 p.m.

Annual street and craft fair with over 100 vendors, live music, and food presented by the Sleepy Hollow – Tarrytown Chamber of Commerce. 

PLEIN AIR Paint Out: Saturday, October 9, 9:00 a.m. – 4:00 p.m., and the auction begins at 4:00 p.m.

Artists working in paint media or watercolor will be located around Pierson Park, creating the artworks which will be auctioned later in the day in the Pavilion. Visitors to the Park on Saturday will be able to watch as these local masterpieces are being created!

Pierson Park 238 W Main Street, Tarrytown.

Paint Your Own Witchy Wonderland: Saturday, October 9; 12:00 p.m. – 3:00 p.m. 

Join Halloween artist Heather Gleason to learn the step-by-step process of painting your own Witchy Wonderland canvas painting! Each participant will receive an 11 x 14″ canvas panel, brushes, and paints. No experience is necessary. Everyone will leave with their very own unique painting and a spooktacular gift handmade by Heather.

Seats are limited and sell out quickly at http://sleepyhollowcemetery.org/special-events/ Sleepy Hollow Cemetery North Gate, 540 North Broadway, Sleepy Hollow.

The TaSH Farmers Market: Saturdays from 8:30 a.m. – 1:30 p.m., through November 20.

The Tarrytown and Sleepy Hollow Farmers’ Market. Farm-fresh fruits and vegetables, artisanal breads and baked goods, meats, poultry, fish, craft spirits, farmhouse cheeses – it’s all here. But that’s where it starts. Each Saturday, May through November, more than 30 vendor stalls hug a sun-dappled, grassy lawn, where the best area musicians entertain. Kids dance and play, friends and families socialize, and everyone eats! Special Halloween-themed activities throughout the fall!

Patriots Park, Sleepy Hollow tashfarmersmarket.org

Adventure Seekers

Rocky’s 5k Run: Saturday, October 16 – Kid’s Race 9:00 a.m.

Beautiful fall foliage is the perfect backdrop for Rocky’s 5K. Challenging hills and wide carriage roads – the perfect race for experienced trails runners and first-timers. If you are familiar with the Rockies, test your stamina and charge those uphills! First 5K? The well-marked course and friendly volunteers will make it enjoyable from start to finish. Overall and age group awards, t-shirts, and refreshments. The course is spectator-friendly, close to parking, and features beautiful terrain – the lake, woodlands, and rolling pastures.

For more information and registration, visit https://www.friendsrock.org/rockys-5k.

Costume Paddle on the Hudson: Saturday, October 16; 4:30 p.m.

Calling all witches, warlocks, wizards, and more! Join the second annual Stand Up Paddle Board (SUP) Witch costume paddle. Keep a watchful eye…the Headless Horsemen may even make an appearance!

For more information and tickets, visit https://rivertownssupyoga.com. Horan’s Landing Waterfront Park, Sleepy Hollow.

Sleepy Hollow 10K Halloween Run: Saturday, October 23 – Kid’s Race 9:00 a.m. (1 mile), 10K 9:30 a.m.

Enjoy the history and scares of Sleepy Hollow as you run for your life along the scenic Hudson Valley course, including a stretch along the Hudson River with views of the Headless Horseman Bridge, Sleepy Hollow Cemetery, and the Old Dutch Church. You never know what might be lurking on the course in Sleepy Hollow… Don’t forget to dress up as best costume wins!

Advance registration is available at www.rivertownrunners.org. Morse School, 30 Pocantico Street, Sleepy Hollow.

Hulda’s Night – The Legends of the Rockefeller State Park Preserve: Thursday-Saturday, October 27-30; 2 programs each night; 6 p.m. & 7 p.m.

An unforgettable night of outdoor theater, history and hiking. Some said she was a witch, others said she was a skilled but misunderstood healer of Bohemian origin. On “Hulda’s Night” a small group gathers at the home of the Preserve Manager guided by torchlight through the dark woods, across wooden bridges and accompanied by the night sounds of the forest. Along the way, they will encounter a storyteller by campfire, reciting local legends and lore, before meeting “The Leatherman” himself.

Tickets are required. Purchase them here – https://visitsleepyhollow.com/huldas-night-at-rockefeller-state-park-preserve/

History Buffs

Irving’s ‘Legend’: October 131; Friday-Sundays at 6:30, 8:00, and 9:30 p.m.

Irving’s ‘Legend’ returns reimagined this fall. Performed for the first time ever outdoors under the stars at Washington Irving’s Sunnyside, master storyteller Jonathan Kruk will cast a spell with dramatic performances of the classic tale. Live music and an appearance from the Headless Horseman himself make this a spooky spectacular experience for all ages.

For more information, visit https://visitsleepyhollow.com/events. Sunnyside, 3 W Sunnyside Lane, Irvington, NY 10533.

Sleepy Hollow Lighthouse Tours are Sundays through October 31; 1:00 p.m. – 3:00 p.m.

The Sleepy Hollow Lighthouse (aka Tarrytown Lighthouse and Kingsland Point Lighthouse) was once a half-mile offshore, warning ships away from dangerous shoals on the east side of the Hudson River. Years of landfill by a now-demolished General Motors factory moved the shoreline within a few feet of the light. The cast iron tower was installed in 1883. Over its 78 years of operation, 12 lightkeepers and their families occupied the five-story structure. Sleepy Hollow’s village historian brings to life stories from the days this was a crucial navigational aid on a busy water highway!

Kingsland Point Park, 299 Palmer Avenue, Sleepy Hollow, NY 10591.

The Historical Society of Tarrytown and Sleepy Hollow: Walking Tours are Saturdays and Sundays in October.

Soak up the history of this famous cemetery by the light of kerosene lanterns! It’s like stepping back in time as you visit some of the most impressive residents, including William Rockefeller, Andrew Carnegie, John Dustin Archbold and others resting in peace in the north end. As this is only a one-hour tour, you’ll need to visit during the day to see Washington Irving’s grave. Tours include “Irving, the Old Dutch Church and the Colonial Experience,” “Heroes and Villains,” and “Walking Through Time.” 

Advance reservations required: www.thehistoricalsociety.net. Sleepy Hollow Cemetery North Gate, 540 North Broadway, Sleepy Hollow.


Drive-In Movie – Ghostbusters: Friday, October 15, Gates open at 5:30 p.m. Movie begins at 6:30 p.m. *Rain date Saturday, October 16.

Who you gonna call? Ghostbusters! Jump in your Ectomobile and head to John Jay Homestead for the 1984 supernatural comedy on the big screen. This special drive-in movie is presented by Friends of John Jay Homestead and Bedford Playhouse.

Tickets and concessions available at www.johnjayhomestead.org.

Sleepy Hollow International Film Festival: Friday-Sunday, October 15-17. Cars arrive at 5:30 p.m.

Enjoy three nights of big-screen double-feature movie mayhem and film shorts under the stars from inside, or outside, your own car! There will be food trucks present as well as concessions! Showing: The Thing (1982), Chopping Mall (1986), Monster Squad (1986), An American Warewolf in London (1981), and more!

Tickets are required – $25 per car/per night available on: www.sleepyhollowfilmfest.com Kingsland Point Park, Sleepy Hollow.

We wish you an enjoyable and spooky Sleepy Hollow experience. For more fun events, check out our Events Calendar!

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Angela Bosco is a native of Westchester. She chose Briarcliff Manor as her home after too many hurricanes in Florida and too many people in NYC. She’s mom to her son, Blaise (2016), who’s energy she simultaneously envies and fears. She shares a love of adult beverages with her husband Michael who, like her, is in the spirits industry. A self-proclaimed expert multi-tasker, you can find her on the Hudson Line cramming podcasts, emails and breakfast while penciling in her eyebrows and trying not to spill coffee on her seat mate during her morning commute to the city. On her free time she struggles to choose between doing yoga, reading NY Times best-seller’s or watching all things Real Housewives: the latter usually wins out. In her 20s you could hear her asking when her life would begin- now in her 30s you’ll find her reveling in it-chaos and all.