Fall Fun for Everyone in the River Towns

It’s that time of year again, when our little towns take the amber-crested spotlight and droves of tourists sojourn to catch all the fall feels, rich in history, scenery and of course, legends.  

With no shortage of things to do this month, here’s our list for the scare-seekers and scaredy-cats alike. 

Family Friendly 

The Blaze continues to excite and delight.  Photo: Historic Hudson Valley

The Great Jack O’Lantern Blazethru November 21st     

Thousands of hand-carved pumpkins illuminate 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. 

Info and tickets pumpkinblaze.org
Van Cortlandt Manor, 525 S Riverside Ave, Croton-On-Hudson 

Home of the Legend-thru November 8th, Fridays-Sundays + Columbus Day: 10:00AM – 3:30PM 

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 info and tickets visitsleepyhollow.com/events
Sunnyside, 3 W Sunnyside Lane, Irvington 

Sleepy Hollow Block Party-Friday & Saturday, October 22nd & 23rd: 7:00PM – 11:00PM 

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

Thrill Seekers 

Sleepy Hollow Cemetery Evening Lantern Tour

Soak up the history of this famous cemetery by the light of kerosene lanterns! It’s like stepping back in time as we 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. Sleepy Hollow Cemetery North Gate, 540 North Broadway, Sleepy Hollow 

Dates: Every evening in October. Weekends and select weekday nights in November.
Buy Tickets Here for Lantern Tour.

Murder Mystery at Sleepy Hollow Cemetery-Saturday, October 2nd: 7:00PM – 9:30PM 

Somebody’s dead at Sleepy Hollow Cemetery (actually, a lot of 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, goals, plots to unravel, and the chance to unmask the killer in your midst.
Buy Tickets on sleepyhollowcemetery.org/special-events 

The Hayride is a spooky good time for families and thrill-seekers alike. (Photo Margaret Fox)

Haunted Hayride– Friday & Saturday, October 22nd & 23rd: 7:00PM – 11:00PM 

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  past the Old Dutch Church, following 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. 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 web site www.sleepyhollowny.gov 

Park at the Sleepy Hollow High School/Middle School at 210 N. Broadway, Sleepy Hollow and walk down to 28 Beekman Avenue. 

Craft Fairs & Markets 

Fall 2021 Westchester Craft Crawl- Sunday October 3rd: 11:00AM-5:00PM  

A free outdoor tour features 30 regional professional craft artists. The Crawl covers 8 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. www.westchestercraftcrawl.com 

Tarrytown: Makers Central, 84 Central Ave. Ossining & Cortlandt Manor (locations TBC) 

Plein Air Paint Out- Saturday, October 9th: 9:00AM-4:00PM, auction begins at 4:00pm 

Artists working in paint media or watercolor will be located around Pierson Park creating the art works 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 artworks are being created.
Pierson Park 238 W Main St, Tarrytown 

Paint Your Own Witchy Wonderland- Saturday, October 9th: 12:00PM-3:00PM 

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 necessary. Everyone will leave with their very own unique painting and a spooktacular gift handmade by Heather. Tickets: sleepyhollowcemetery.org/special-events/
Sleepy Hollow Cemetery North Gate, 540 North Broadway, Sleepy Hollow 

Adventure Seekers 

Witches Stand Up Paddle Board (Photos on the Fly @photosonthefly)

Costume Paddle on the Hudson– Saturday, October 16th : 5pm 

Calling all witches, warlocks, wizards, and more for the 2nd annual Stand Up Paddle Board Witch costume paddle. Keep a watchful eye…the Headless Horsemen may even make an appearance. 

Info and tickets: rivertownssupyoga.com. Horan’s Landing Waterfront Park, Sleepy Hollow 

Sleepy Hollow 10K Halloween Run– Saturday, October 23rd: Kids Race 9:00 am (1 mile), 10K 9:30am 

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. Don’t forget to dress up as best costume wins. Advance registration available at www.rivertownrunners.orgMorse School – 30 Pocantico Street, Sleepy Hollow 

Hulda’s Night-The Legends of the Rockefeller State Park Preserve– Thursday-Saturday, October 27th-30th: 6pm & 7pm 

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 torch light 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 required visitsleepyhollow.com/huldas-night-at-rockefeller-state-park-preserve 

History Buffs 

Jonathan Kruk casts a spell in “Irving’s Legend” at Sunnyside (Photo: Historic Hudson Valley)

Irving’s ‘Legend’-October 1st – 31st, Friday-Sundays at 6:30, 8:00 and 9:30PM 

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 make this a spooky spectacular experience for all ages. Irvingtonvisitsleepyhollow.com/events
Sunnyside, 3 W Sunnyside Lane 

Sleepy Hollow Lighthouse Tours-Sunday’s, October 10th, 17th, 24th, 31st: 1:00PM-3:00PM 

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. Twelve light keepers and their families have 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 

The Historical Society of Sleepy Hollow and Tarrytown: TarryHollow Walking Tours – Saturdays and Sundays in September and October

Step back in time to “meet” men and women who fought in the Revolutionary War and inspired Washington Irving to write “The Legend of Sleepy Hollow.” You’ll learn about the lords of Philipsburg Manor, and the men and women enslaved on the Manor in “Irving, The Old Dutch Church and the Colonial Experience.” The Historical Society also offers “Heroes and Villains of the Hollow” (Sleepy Hollow history) and “Walking Through Time” (Tarrytown history). Proceeds support preservation of the Old Dutch Church, the Burying Ground and The Historical Society’s Jacob Odell House. Advance reservations required:  www.thehistoricalsociety.net.


Sleepy Hollow International Film Festival-Friday-Sunday, October 15, 16 and 17. Cars arrive at 5:30 PM 

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 as well as concessions. Showing: “The Thing” (1982), “Chopping Mall” (1986), “Monster Squad” (1986), “An American Werewolf in London” (1981) and more. Tickets required-$25 per car/per night available www.sleepyhollowfilmfest.com
Kingsland Point Park, Sleepy Hollow 

Rocky Horror Picture Show-Friday, October 30 9pm
For the young-at-heart crowd, Paramount Hudson Valley Theater is showing cult classic Rocky Horror Picture Show, complete with a live “shadow” performance by a cast of Hudson Valley actors named Apoca-Lips. A “shadow cast” is an ensemble of artists that act out the movie as it is playing, dancing and singing live. They also serve as cues to let the audience know when to participate. 

Tickets $10. 1008 Brown St, Peekskill www.paramounthudsonvalley.com

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About the Author: Angela Bosco