PINE PLAINS — Robert L. Harpp Jr., 57, passed away unexpectedly on March 1, 2025 in Great Barrington. He was born on Feb. 10, 1968, in Sharon, Connecticut, the son of the late Robert L. Harpp Sr. and Judy (Shook) Harpp.
Bobby graduated from Pine Plains Central School in 1986, where he excelled at baseball. After graduation he went to Columbia Greene Community College, where he studied criminal justice.
He loved all sports, but his passion was baseball. He was instrumental in sharing his love for the sport by coaching baseball in Pine Plains since he was a teenager. He was also an avid New York Yankees fan.
In 1992, he joined the Dutchess County Sheriff’s Department where he would become a detective, arson investigator, and hostage negotiator. After his time in law enforcement, he served as Pine Plains Court Clerk. Most recently he worked as the Director of Security for Calyx in Great Barrington, a job that he enjoyed and made many friends and connections throughout the community.
He was truly a people person with a unique ability to build friendships wherever he went, often leaving a lasting impression by giving everyone a special nickname.
Above all else, Bobby was most proud of his children and their accomplishments. He played an essential role in their success, instilling in them the same determination, creativity, and dedication that defined his own life.
Bobby is survived by his devoted children; Abigail J. Harpp and Nolan Thomas Harpp; and his loving mother Judy Harpp. He is also survived by his sister Lenora Carr, her husband Jeff, and nephew Austin. He was predeceased by his father Robert L. Harpp Sr. and his brother Thomas J. Harpp.
A celebration of Bobby’s life will be held on March 15 from 1 to 4 p.m. at the Pine Plains Lions Club Pavilion.
For directions or to leave a message of condolence for the Harpp family, please visit www.peckandpeck.net.
In lieu of flowers, the family kindly requests that memorial contributions be made in Bobby’s memory. Please make donations payable to Judy Harpp, PO Box 149, Pine Plains, NY 12567, with the understanding that the funds will be directed to the Pine Plains Recreation Department.
Justine and Victor Valla in their studio with a painting of Victor’s,”Jonah and the Whale.” Robin Roraback 
A ceramic vase by Kathleen Heidemann.Provided 
Joy Brown’s delightful ceramic sculptures.Provided 
Hundreds of items at Stateline Auctions, including a candy-apple-red Crosley pickup truck.D.H. Callahan
