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The headless horseman rides again at The Players

The Players expands its production of the classic tale of 'The Legend of Sleepy Hollow,' just in time for Halloween.

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  • | 2:10 p.m. October 14, 2021
Philip Troyer plays Ichabod Crane in The Players Centre for Performing Arts "Legend of Sleepy Hollow."
Philip Troyer plays Ichabod Crane in The Players Centre for Performing Arts "Legend of Sleepy Hollow."
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Let’s face it. Everyone loves a ghost story—and what better time to indulge in this pleasure than Halloween?

For the past five years, The Players Centre for Performing Arts recognizes that the locals’ timeless love of a good ghost story is engrained in Washington Irving’s classic, "The Legend of Sleepy Hollow," and Irving’s short story has never failed to terrify and entertain us for the past 200 years.

Beginning Oct. 22, The Players will host four dates at two, separate outdoor venues of the spooky production (Sarasota Polo Club in Lakewood Ranch, and at Selby Botanical Gardens’ Historic Spanish Point). Families and people of all ages will particularly enjoy the story’s main character, Ichabod Crane — a tall, lanky character who is the local schoolmaster and has a strong belief in all things supernatural, including the legend of the headless horseman.

If you need a memory refresh on the theme of this 1790s tale, Crane eventually begins courting an heiress, a decision which angers a local man who also wishes to marry her. After asking for her hand in marriage, Crane is headed home alone at night when the headless horseman appears and chases the schoolmaster. Crane is never seen again.

Thirty-six-year-old Philip Troyer plays the role of Ichabod Crane and says he thoroughly enjoys playing the character, particularly because he loves looking out into the audience and seeing the families who are mesmerized by the show. It helps him to exaggerate his otherwise shy personality. 

“I’ve been playing the role for four years now, and I love the fact that the character is over the top and outlandish,” says Troyer. “That’s not me in real life. It allows me to transform. I especially love to speak with a distinct British accent like they did in the late 1700s,” he says.

Troyer volunteers his time as an actor, but his day job is working as a designer with The Rhinestone World, a Bradenton-based national custom jewelry manufacturer. He grew up in Sarasota and considers himself “a Sarasota lifer.” His love of theater stems from his middle school days when he performed in shows and loved every minute of it. He went on to study photography at the International Academy of Design and Technology.

The headless horseman always steals the show in the
The headless horseman always steals the show in the "Legend of Sleepy Hollow."

Jeffery Kin,  producing artistic director at The Players, says the idea of producing "Sleepy Hollow" was conceived over five years ago when he was driving around the Lakewood Ranch area thinking of ideas for show productions. “I heard the distant sound of a neigh from a horse,” Kin says. “It was an aha moment for me, and I thought of 'Sleepy Hollow' immediately."

Kin says he also likes the idea of establishing community traditions, of which Lakewood Ranch only had a few at the time. He saw the production as an opportunity to draw and entertain families and folks of all ages. He adds the classic tale teaches valuable life lessons to kids, such as two of the seven deadly sins: greed and gluttony.

This year is the first the production will add a second venue to the mix, with three performances at Historic Spanish Point.  "We were touring Historic Spanish Point and thought it would be an ideal location to take our Sleepy Holly production. [Marie Selby Botanical Gardens] has been enthusiastic about their partnership with us ever since we hosted Broadway on the Bay at their Selby Botanical location on North Tamiami. It made sense for us to use their Historic Spanish Point location for the 'Sleepy Hollow' show."

This will be the last season for Kin, who, after 15 years with The Players, will leave in January to be the new general director of a proposed citywide arts festival.  Planned by the Arts and Cultural Alliance of Sarasota in conjunction with the Sarasota Downtown Improvement District, the festival's goal is to bring greater awareness to the Sarasota area arts and culture scene and possibly draw national and international attention and help local businesses.

“I hope that the Players Centre will continue to be mobile and really get out into the Sarasota communities, getting to know our neighbors, drawing families to us and giving them a legacy," he says. "This is a major initiative for us and we know it has amazing potential for growth, not just in Lakewood Ranch and in Historic Spanish Point, but everywhere in Sarasota."


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