David B. Cleveland, 62, of Greenfield, passed away peacefully on May 5, 2026. Born on October 22, 1963, to Constance J. (Ruthurfurd) Sipe and the late Elmer C. Cleveland, David had a deep love for music and especially enjoyed playing the trumpet. He also loved baseball and golf and worked as a truck driver in the waste management industry for many years. David leaves his beloved life partner of twenty years, Jennifer Caples of Greenfield, MA; his stepdaughters, Lydia Caples and Devyn Caples, both of Greenfield, MA; his mother, Constance J. (Ruthurfurd) Sipe of Camino, CA; his brothers, Robert “Bobby” Cleveland of Placerville, CA, and John and Robin Cleveland of Camino, CA; and his sister, Karen Cleveland of Boise, ID; and many nieces and nephews who loved him dearly. A memorial service will be held to honor David’s life at John and Robin Cleveland's home in Camino, California on July 11, 2026, at 11AM. Family and friends are invited to attend. New England Funeral & Cremation Center, 25 Mill Street, Springfield, MA has been entrusted with the arrangements. Please visit David’s memorial page at www.nefcc.net to share expressions of sympathy.