Sleepy Hollow Announces Full Slate of Halloween-Themed Events

Sleepy Hollow ushers in Halloween season with a full calendar of family friendly events. From Hayrides — to a glass pumpkin patch — to a Washington Irving-inspired circus, Sleepy Hollow continues its tradition as a regional destination for Halloween-themed events, experiences and entertainment.

World Premier of The LEGEND
On Friday, September 23, The Village of Sleepy Hollow hosts the world premiere of The LEGEND, a gravity-defying cirque theatre performance commemorating the bicentennial of The Legend of Sleepy Hollow. Weekend evening and matinee performances continue through October 16.

“The LEGEND” is a simmering adaptation of Washington Irving’s iconic ghost story, “The Legend of Sleepy Hollow.” Audiences will be treated to a cirque/theatre noir production with narration by Washington Irving himself – in hologram form.

“This will also be the first time in the history of American circus that an animal act has been presented holographically in a circus tent…but you’ll have to see the show to experience the surprise,” says Carlo Pellegrini, of Westchester Circus Arts.

Under a big-top tent that intimately seats 220, performers will soar above the audience in a production created by Westchester Circus Arts, written by longtime circus creator/producer Carlo Pellegrini with staging by the director Hilary Sweeney.

“We’re excited to host another Westchester Circus Arts production,” said Sleepy Hollow Mayor Ken Wray. “Halloween gives us an opportunity to work with local creatives to celebrate our timeless cultural treasures,” Wray continued.

Westchester Circus Arts was commissioned by the Village of Sleepy Hollow to create ‘The LEGEND. Other productions by Westchester Circus Arts include NEVERMORE, CIRCUS LATINO, and CirqueFEST.

Tickets are available at

Photo: Margaret Fox

Sleepy Hollow Cultural Festival
Saturday, September 17, 11:00 am – 7:00 pm
Kingsland Point Park

Sleepy Hollow’s annual Culture Festival will be held Saturday, September 17th at Kingsland Point Park from 11am-7pm featuring music, food, drinks, Kids entertainment (bouncing castle, clown, magician) and more! Admission is free. A $5 parking fee applies, however, a free shuttle bus will be provided from Beekman Avenue. Visit for more information

10th Annual Oktoberfest
Saturday, September 24, 1:00 – 5:00pm
Kingsland Point Park

A day of music, food, bouncy castles and refreshments at the Kingsland Point Park Kathryn Davis River Walk Center. Admission is free. (parking requires a separate $5 fee) Visit for more information

Photo by Margaret Fox

Sleepy Hollow Street Fair
Saturday, October 8, 10:00 am – 4:00 pm
Beekman Avenue

Featuring over 70 vendors, a kid’s carnival, music and food from local restaurants. Presented by the Sleepy Hollow Tarrytown Chamber of Commerce. Visit  for more information.

Glass Pumpkin Patch (NEW)
October 14 – 16, 10:00 am – 5:00pm
Kingsland Point Park

For the first time, visitors can walk through a maze of hay bales featuring special hand-blown glass pumpkins. Proceeds from the sale of the glass pumpkins benefit the Make-A-Wish Hudson Valley Chapter. This great gift shopping and fundraising opportunity was the brainchild Sleepy Hollow’s Recreation Superintendent, Matt Arone. Food trucks will be available. The event is free to the public, although a parking fee will apply. Visit for more information.

Photo by Tim Grajek

SUP Witches Festival at Horan’s Landing
Sunday, October 16, noon – 4:00 pm (Rain date October 23.)

If you are searching for a wicked sight, come to Horan’s Landing for the 3rd Annual SUP Witch Paddle. Witches will gather and “The Legend of Sleepy Hollow,” will be told. Join the witches on the water or stroll along the riverwalk. Vendors, food, brews and spooky views are available. Costumes encouraged! All paddlers must register in advance to participate at Registration starts September 16.

Photo: Joe Golden

Sleepy Hollow Haunted Hayride & Block Party
Friday, October 21 – Saturday, October 22. Block party begins at 5:00 pm, Hayrides 7:00 pm – 11:00 pm.

The Haunted Hayride legend rides again into the dark night where ghosts and goblins loom. Time entry, advanced purchase required for hayrides only. Tickets at No fee for the block party that features food, music and bouncy castles.

Sleepy Hollow “Run For Your Life” Halloween 10K
Saturday, October 29, Kids race, 9:00 am, 10k, 9:30am at Morse School

Experience historic and scary sites along the scenic Hudson Valley course. A best costume prize will be given. Advance registration at

Photos attached

For more information visit


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