Less than a week after 12-year-old Levi Dempsey died following a utility terrain vehicle crash in Maplecrest, a summer concert at CD Lane Park became a fundraiser for his family.
Hundreds of community members gathered at the park in collective grief on County Route 56, also known as Big Hollow Road, on Aug. 7. The Windham Chamber of Commerce raised at least $2,300 through raffle ticket sales and donations, while the Windham Hose Company collected additional contributions by selling food and drinks. The chamber hosts a concert in the park once a month from June to September, sponsoring a local group or organization. Windham Hose had already been selected for the August concert, and organizers quickly recast the event as a benefit for the Dempsey family.
“It just turned out that Windham Hose happened to be our partner, it was already pre-planned,” said Lisa Jaeger, chair of the chambers board of directors and member of Windham’s planning board. “For us to pivot to having Mr. Dempsey’s family be the recipient of anything we do here, it’ll help people heal and give them some financial relief.”
Levi’s father, Ryan Dempsey, is the second assistant chief of the Windham Hose Company.
Levi, 12, died following the July 31 crash near 84 County Route 56. He was ejected from a utility terrain vehicle and pinned beneath it before being airlifted to Albany Medical Center, where he was pronounced dead.
He was not alone in the vehicle—the crash injured three other children, ages 14, 11, and 10.
The 10-year old, identified as Levi’s younger brother, Cade Dempsey, remained hospitalized in critical condition as of Aug. 10.
None of the children were wearing a seatbelt or helmet, according to the Greene County Sheriff’s Office.
An online fundraiser, launched shortly after Levi Dempsey’s death, had raised over $149,000 as of Aug. 12.
The two boys are the youngest of Ryan and Alisa Dempsey’s six children. In addition to serving as a volunteer firefighter with Windham Hose Company, Ryan Dempsey is a pastor at Mitchell Hollow Mission Church.
Light rain fell during the fundraiser, where the chamber held a 50-50 raffle as well as a raffle for a wooden cross draped with an American flag, donated by Gilboa-based Garage Beers Woodworks.
Greg Thorpe, member of the Windham Hose Company, collected donations as locals lined up to order food.
“The rain really held it back a little,” he said. “But between social media and the radio, and people knowing all the proceeds would go to the Dempsey family, that helped a lot as far as the traffic.”
“It’s been good,” he said.
Cairo-based Round Top Knit and Screening Inc. also donated customer wristbands for the fundraiser on short notice, Thorpe said.
“Our vice president’s daughter happened to think of it,” he said. “We headed down to Round Top and they were able to get them on really short notice. They put a special order in.”
Between the raffles and food, visitors to the park line-danced to music by Albany-based country music group Tame the Rooster. A balloon artist circulated through the crowd as others gathered near the playground and took in mountain views.
The sun emerged later in the evening despite thunderstorms forecasted for the night.
“Maplecrest has always been known to have its own little climate,” Jaeger said.
“For us, this weather is normal,” Jaeger said. “We’re hardy folk.”
Connor Greco is a staff reporter for The Overlook covering Windham, Hunter, and surrounding Greene County communities. Send correspondence to connor@theoverlooknews.com.







