Sleepy Hollow, NY

Join In On All The Fun and Festive Activities in Sleepy Hollow This October!

Out and About Westchester NY

Oh all the fun activities are upon us for Halloween! With Sleepy Hollow and Tarrytown right in our backyard, there is something spooky and exciting to do every night to get into the spirit of Halloween. Here is a list of events to partake in October.

Sleepy Hollow Street Fair- This annual street fair has become a popular event for everyone in Westchester to look forward to. Food and craft vendors lining up Beekman Ave to celebrate the most wonderful time of the year. Don’t forget to grab a Sleepy Hollow t-shirt as a souvenir!
Sleepy Hollow Street Fair

Jack O’ Lantern Blaze- Coming to the jack o lantern blaze is a must for this Halloween. Surrounded by thousands of hand carved pumpkins for each exhibit ranging from pirate ships to windmills and of course, the headless horseman bridge. It is one of the most spectacular events to see in person. Get your tickets now before they sell out.
Jack O' Lantern Pumpkin Blaze

Tarrytown Halloween Parade- The annual Tarrytown Halloween parade is celebrating 20 years! Come join all Halloween loving spectators observing who are going to show up as the best costume in all of the parade. Prizes given out for all the best costumes, floats and more! Don’t forget to bookmark this event!
Tarrytown Halloween Parade

Sleepy Hollow Cemetery Evening Tours - Visiting Sleepy Hollow cemetery in October at night is already spooky as it is but once you join this walking tour with different themes from murder to mayhem and the good, the bad and the unusual, you will be entertained by the knowledgable tour guides telling you all of Sleepy Hollow cemetery’s dark past and secrets. While you’re there don’t forget to visit Washington Irving’s grave!
Sleepy Hollow Cemetery Tour

Sup Witches Festival- This relatively new event is in its third year and it has created quite the stir around Sleepy Hollow but now through all of Westchester. Watching at least 80 people dress as witches paddleboard on the Hudson river towards the Sleepy Hollow lighthouse is quite a sight. This year more witches are expected to join. Food trucks and vendors will be at the event.
Sup Witch's Festival

Haunted Hayride- The annual sleepy hollow haunted hayride is everything you can imagine. Spooky and blood curdling are a couple of words to describe this favorite Halloween ride. Taking you through the Old Dutch Church and the bridge where Ichabod Crane met his fate, this is something you’ll want to see for yourself. Tickets sell out fast for the haunted hayride!
Sleepy Hollow Hayride

Irving’s Legend- It is a privilege to see Jonathan Kruk in his element captivating audiences as he tells the classic story of Sleepy Hollow and the Headless Horseman. Performing at Washington Irving’s home, Sunnyside it is certainly a must to watch Jonathan tell one of the greatest stories of all time.
Jonathan Kruk

The Legend- This show is something like no one has ever seen before. A Cirque themed performance inspired by the Legend of Sleepy Hollow with aerial dancers, acrobats and a hologram of Washington Irving narrating his very own story. Everyone is already raving as a must see!
The Legend Musical

Check out the entire list of events in Sleepy Hollow and Tarrytown on this link.

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