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Sleepy Hollow Halloween Events You Won’t Want to Miss

By September 12, 2018September 14th, 2023No Comments
Sleepy Hollow Halloween Events You Won’t Want to Miss

Our area is pretty much synonymous with Halloween thanks to The Legend of Sleepy Hollow. We also happen to boast some of the best Hudson Valley fall foliage. So, come autumn, things really get exciting in the Rivertowns. When we’re not straightening teeth with braces and Invisalign in Tarrytown, the team here at 914 Orthodontics will definitely be taking advantage of all of the spooky fall fun. Here are the 2018 Sleepy Hollow Halloween events (and a few in the surrounding area) that we’re putting in our calendars:

Sleepy Hollow Cemetery Tours – 540 North Broadway, Sleepy Hollow – No Sleepy Hollow, NY Halloween is complete without a cemetery tour. While tours are available April through November, they always feel creepiest in the fall. Take an evening lantern tour to see the grave of Washington Irving and a number of other notable folks like Andrew Carnegie and William Rockefeller. Throughout September and October, there are also a host of special activities, including a murder mystery, tavern sign painting and ghost stories. Browse the schedule and purchase tickets here.

The Great Jack O’ Lantern Blaze – Van Cortlandt Manor, 525 S. Riverside, Croton-on-Hudson – The Great Jack O’ Lantern Blaze is one of the most family-friendly Halloween events in Sleepy Hollow country and it’s appropriate for all ages. Held at Van Cortlandt Manor in Croton-on-Hudson, it’s among the largest Halloween-themed extravaganzas in the country. The unique spectacle features more than 7,000 hand-carved jack o’ lanterns, sound effects, elaborate lighting and an original soundtrack by Richard Christy. The Great Jack O’ Lantern Blaze 2018 will run on select evenings from September 28 through November 24. Last year, most nights sold out, so purchase tickets in advance.

Sleepy Hollow Haunted Hayride – Sleepy Hollow Village Hall, 28 Beekman Avenue – The Sleepy Hollow Haunted Hayride is one of our favorite annual traditions. Who doesn’t like getting a little scared? Hop on the hayride and keep an eye out for the Headless Horseman as you make your way downtown, through the woods and into the old cemetery. Prior to your ride or after, enjoy the free block party on Beekman Avenue, which will be complete with music, food and vendors. The block party and Sleepy Hollow Haunted Hayride 2018 dates will be Friday, October 26 and Saturday, October 27. Tickets usually go on sale towards the end of September, so stay tuned since they sell out fast.

Horseman’s Hollow – Philipsburg Manor, 381 N. Broadway, Sleepy Hollow – If you’re looking for Sleepy Hollow Halloween events for kids, this is definitely not it! Horseman’s Hollow takes the Legend of Sleepy Hollow up a few notches and it’s pretty terrifying. Horseman’s Hollow is more appropriate for adults, teenagers and maybe really brave older kids. Throughout October, the historic Philipsburg Manor is transformed into a dark, scary land under the Headless Horseman’s rule. Vampires, witches, ghouls, ghosts and a variety of creatures will be hiding in the shadows and trying to prevent you from leaving the Hollow. The attraction features professional actors and cutting-edge special effects for a seriously spooky experience. You’ll walk a haunted trail, enter Ichabod’s schoolhouse for a maze of horrors and then head into the Horseman’s lair. The dates for 2018 are October 5-7, 12-14, 19-21 and 25-31. Tickets will go on sale on September 4 and can be purchased here.

Irving’s Legend – Old Dutch Church with Parking at Philipsburg Manor, 381 N. Broadway, Sleepy Hollow – Jonathan Kruk, a master storyteller, will put on a dramatic performance of Washington Irving’s tale with a backdrop of organ music by Jim Keyes. One of the coolest Sleepy Hollow, NY Halloween events, Irving’s Legend is geared towards those ages 10 and up. Performances will be held at the Old Dutch Church on October 5-7, 12-14, 19-21 and 25-31. Ticket sales start September 4. Get them here!

Sunnyside: Home of the Legend – Washington Irving’s Sunnyside, 3 W. Sunnyside Lane, Irvington – Go deeper into the Legend of Sleepy Hollow in Irving’s home. This daytime Halloween event in Sleepy Hollow country is great for families. Visitors will tour the house, hear about what spurred Washington Irving to write his classic tale and see works of art inspired by it. You’ll also get to check out previously unseen items from the Historic Hudson Valley’s collection, do Headless Horseman arts and crafts and play historic games. The dates this year are Saturdays and Sundays, October 6-7, 13-14, 20-21 and 27-28.

Jay Ghouls’ House of Curiosities – Lyndhurst, 635 S. Broadway, Tarrytown – Our favorite Tarrytown Halloween activity is back and this year’s Jay Ghoul’s House of Curiosities is all about classic mystery stories. When you arrive for the 40-minute performance, you’ll be smack dab in the middle of an archeological dig site in 1922. The archeologists have just uncovered an ancient Egyptian tomb and they mysteriously die right after. You’ll solve the mystery during your journey through the mansion. While you’re waiting for your turn to tackle the mystery, you can enjoy activities, food, shopping and Halloween movies in the Welcome Center and walk through the scarecrow and skeleton invasions on the path to the Welcome Center. Jay Ghoul’s House of Curiosities isn’t overly scary and it’s ideal for school-aged kids, teens and adults. Tickets are available for numerous times between 6pm and 9:15pm on Friday, October 19 through Sunday, October 21, Thursday, October 25 though Sunday, October 28 and Wednesday, October 31. Purchase tickets here.

Tarrytown Halloween Parade – Starts at Patriot’s Park and ends on Main Street, Tarrytown – The Tarrytown Halloween Parade was named “Best of Westchester” four years in a row. The parade starts at Patriot’s Park, makes it way down Broadway and ends on Main Street where a block party kicks off with live performances, a DJ, dining and fun. The 2018 Tarrytown Halloween Parade is scheduled for Saturday, October 27 at 5:30pm with a rain date of Sunday, October 28.

Want to perfect your smile with braces or Invisalign in Tarrytown in between your Sleepy Hollow Halloween events? Schedule a free consultation at 914 Orthodontics. Book your visit online or by calling or texting us at (814) 332-0900!


Dr. Kothari

Author Dr. Kothari

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