Best Spooky Events in Sleepy Hollow Country October 2017

Best Spooky Events in Sleepy Hollow Country October 2017

For a Halloween to remember, discover Sleepy Hollow Country. Located 25 miles north of New York City is the town of Sleepy Hollow, made famous from Washington Irving’s The Legend of Sleepy Hollow. During the Halloween Season there are tons of local activities to help put you in the spirit of things.


Horseman’s Hollow at Phillipsburg Manor

Weekends in October

A haunted trail through Phillipsburg Manor lets you explore a town driven mad by the Headless Horseman. This is a fun and frightful event and is recommended for people age 10 and up.


Great Jack O’Lantern Blaze at Cortlandt Manor

Weekends in October through November

Ramble through historic Cortlandt Manor to discover amazing displays all made of jack o’lanterns! Displays are completed with synchronized lighting, sound effects and sound track. Have a fun Halloween event with the whole family.


16th Annual Village of Tarrytown Halloween Parade

October 28th at 5:30pm

Starts at Patriot’s Park and travels to Main Street in Tarrytown where it turns into a block party. The parade includes marching bands, floats , & Circus Performers. Come for the fun, stay for the block party and enjoy dining on the street with food from local restaurants and food trucks. DJ and live performances. Fun for the whole family!


Sleepy Hollow Cemetery Tours

Weekends through November: Daytime and Evening Lantern Tours

Sleepy Hollow Westchester October 2017

Trace the footsteps of Washington Irving’s most famous character Ichabod Crane in “The Legend of Sleepy Hollow” as we walk to the author’s final resting place during this one-hour walking tour. Learn more about the talented Mr. Irving and his influence on popular culture today.


Haunted Hay Ride

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.


For more information or answers to your insurance questions, contact us at Allan Block Insurance Agency,, located in Tarrytown, NY in the heart of Westchester County, a key business district near New York City.  We write auto, home, renters, condo, co-op, personal, business, life and group insurance for clients locally and in NYC, CT, NJ, PA, MA and many other states. The Professional Agency with the Personal Touch.

Give us your questions, feedback and opinions on this topic.