Sleepy Hollow Halloween 10K

Morse School 30 Pocantico Street, Sleepy Hollow

Enjoy a remarkable course that takes you through Historic Sleepy Hollow’s treasured sights including a stretch along the Hudson River with views of the Headless Horseman Bridge, Sleepy Hollow Cemetery …

$40 – $50
Event Series Lyndhurst Tours

Lyndhurst Tours

Lyndhurst 635 South Broadway, Tarrytown

Lyndhurst, one of America’s finest Gothic Revival mansions, overlooks the Hudson River in Tarrytown, NY. The estate was shaped for more than a century by three families and their staff: The …

$18 – $42
Event Series Home of the ‘Legend’

Home of the ‘Legend’

Sunnyside 3 W Sunnyside Lane, Irvington

At this family-friendly happening, visitors can tour Washington Irving’s house—decorated for the season—watch an original shadow puppet short film, and enjoy games on the lawn. A special exhibit highlights how …

$15 – $18
Event Series Kykuit Tours

Kykuit Tours

Philipsburg Manor 381 North Broadway, Sleepy Hollow

Built between 1906 and 1913, Kykuit was home to four generations of the Rockefeller family. In 2023 the site will be open for guided walking tours Friday-Sunday from May 12-October …

$20 – $65
Event Series The Legend Cirque

The Legend Cirque

East Parcel 60 Continental Street, Sleepy Hollow

The Legend Cirque is back by popular demand for a second season. Step into the magic of the Big Top and witness The Legend of Sleepy Hollow come to life …

$45 – $50

Nyack Halloween Parade

Nyack Main Street, Nyack

Festivities begin at 3:00 pm and continue into the evening. Nyack’s Main Street and South Broadway will be closed for the day’s celebrations. The parade will step off promptly at …

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Tarrytown Halloween Parade

Patriots Park Patriots Park, Tarrytown

The 20th annual Village of Tarrytown Halloween Parade steps off at 5:30 pm from Patriot's Park. March south along Broadway to Tarrytown's Main Street. Block party to follow on Main …

Event Series Lyndhurst After Dark!

Lyndhurst After Dark!

Lyndhurst 635 South Broadway, Tarrytown

You’ve experienced the splendor of the Lyndhurst Mansion during the day, but have you seen it draped in candlelight? Come experience the history of the Mansion and explore Victorian lore …

$35 – $40
Event Series The Man Behind the Legend

The Man Behind the Legend

Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow

Meet the man behind the Legend! In his most famous short story Washington Irving says of Sleepy Hollow Country, "If ever I should wish for a retreat whither I might …

Event Series Tarrytown Music Hall Performances

The Mavericks

Tarrytown Music Hall 13 Main Street, Tarrytown

PLEASE NOTE: The Saturday show begins at 9pm, due to the Tarrytown Halloween Parade. Come early to experience Westchester’s best Halloween event! A Halloween weekend tradition continues! The Mavericks return …

$55 – $95

There’s something for everyone in Sleepy Hollow Country—farmers markets, live music, street fairs, historic homes, hiking trails, kayaking and boating on the Hudson River. Halloween season brings even more for the whole family—haunted hayrides, blazing pumpkins, costumed 10K run, Halloween parade, and of course, the Headless Horseman! For the latest on Fall events, visit our guide to Halloween in Sleepy Hollow.