October 31, 2013 - Photos by Patrick Tewey Three-hundred ... night at Sleepy Hollow (N.Y.), Pock and Catalfumo combine to form the scariest mascot in the country. The duo comprise the Headless Horseman, the long-time Sleepy Hollow mascot....

3 days ago - The Headless Horseman mascot for Sleepy Hollow High School, in Westchester County, New York, has been referred to as "America's scariest high school mascot". Since 1983, Conner Prairie Interactive Historic Park in Fishers, Indiana has held a Headless Horseman festival celebrating the legend ...

August 24, 2026 - Sleepy Hollow High School (SHHS) is a high school located in Sleepy Hollow, Westchester County, New York, United States. It is part of the Union Free School District of Tarrytowns. The mascot is the Headless Horseman. It is consistently ranked in the top 5–10% of high schools in New York State.

6 days ago - The Westchester town has possibly the nation's spookiest high school mascot – a Headless Horseman who leads the football team onto the gridiron in a nod to Washington Irving's epic tale, "The Legend of Sleepy Hollow."

October 7, 2015 - Posted by u/Nacho_friend - 5 votes and 5 comments

September 23, 2024 - As legend goes, at least according ... the ghost of a solider from the Revolutionary War, who haunts the town in ghostly form in search of his missing head. On nights where Sleepy Hollow High School hosts home football games in the village some 30 miles upstate from Manhattan, the storied tale lives on. The high school has a pregame tradition where its mascot, a literal headless horseman, leads the ...

October 3, 2021 - TIL The Sleepy Hollow High School's mascot is the Headless Horseman · r/todayilearned • · upvotes · · comments · What’s Sleepy Hollow, NY like? r/howislivingthere • · upvotes · · comments · Tarrytown / Sleepy Hollow schools · ...

June 8, 2018 - New York's Sleepy Hollow High School broke out the mascot for its homecoming game. Check out the mascot, via Max Preps: The high school has done this every homecoming for years. John Catalfumo serves as the headless horseman, and the horse's ...

October 2, 2021 - TIL There is a high school called Sleepy Hollow High in Tarrytown, New York with a headless horseman as their mascot

October 31, 2024 - Leora Dillon, aka The Headless Horseman, and her horse Eagle, lead the Sleepy Hollow football team onto the field prior to game against Irvington at Sleepy Hollow High School Oct, 19, 2024.

Might be the greatest mascot in high school football 🔥 (🎥: corinthian_cecllc/TikTok) #headlesshorseman · #highschoolfootball · #hsfb · original sound - The Washed Athlete · 00:00 / 00:00 · 95.8K · 872 · 5550 · 13.5K · CBS Sports ...

September 16, 2026 - Sleepy Hollow’s Headless Horseman has been called the coolest high school football mascot after a viral team entrance clip.

3 days ago - A group of high school players comes onto the field, led by their mascot: a black-clad rider on horseback with no discernible head, made famous in Washington Irving’s “The Legend of Sleepy Hollow.” Now it’s time for kickoff for the Sleepy ...

2 weeks ago - The Sleepy Hollow High School's mascot is the Headless Horseman. American writer, Washington Irving wrote 'The Legend of Sleepy Hollow' in 1820 which took place in the area.

September 16, 2026 - Before home games, a real equestrian dressed head-to-toe as the terrifying Headless Horseman emerges onto the dark field. The mysterious figure leads the varsity squad out of the tunnel while riding a striking, jet-black horse. Such was the case this week, which is why they are being called the coolest mascot in high school football.

The Headless Horseman mascot for Sleepy Hollow High School, in Westchester County, New York, has been referred to as "America's scariest high school mascot".[22]

October 28, 2025 - The rebrand worked and the town embraced its new identity. The Headless Horseman became the town's unofficial mascot – and the official mascot of the local high school.