David Wayne Cheschi

Mr. David W. Cheschi, 60, of Milford, MA, passed away unexpectedly at his residence on Friday, March 6, 2026.

David was born in Rochester, NH, the son of the late Louis J. Cheschi Jr. and the late Dianne L. (Miller) Chambers. He attended Milford public schools and graduated from Milford High School, Class of 1983. He later studied electronics at a local community college.

Following his graduation, David began his career at Waters Associates in Milford, but his true calling was always found on two wheels. What began as a childhood fascination with dirt bikes eventually evolved into a lifelong career and a testament to his entrepreneurial spirit. David turned his passion into a profession, founding and operating Dirt Cycle Salvage, first in Hopedale and later in Mendon, as well as Stator Corporation in Mendon.

Whether fixing a stator, or riding on a trail, buying, selling, or collecting, he was always in his element and respected by many for the expertise he brought to his work.

When he wasn't working, David enjoyed playing poker. A skilled Texas Hold 'em player, he competed in numerous tournaments and earned a reputation for his sharp play. Many of these games took place at Foxwoods, a place that held special significance for him and his family.

Beyond the cards and the casino floor, Foxwoods served as the backdrop for cherished family vacations. While David enjoyed the camaraderie of the poker room, his children remember those trips for the simple joys of room service, afternoons by the pool, fun in the arcade, and the adrenaline of the motion movie ride.

These childhood moments remain some of their most treasured memories, and they remain deeply grateful for the fun and adventure their father provided. David leaves behind a legacy of hard work, a passion for the ride, and a family who will forever carry his spirit in their hearts.

David is survived by his three children: Sara Cheschi of Millville, MA; Stevie Lee Cheschi and her partner Andrew Redquest of Norwood, MA; and David Cheschi of Milford, MA. He also leaves behind three grandchildren: Aidin Rawlinson, Adalyn Rawlinson, and Colton Redquest. He is also survived by his former wife, Carol A. (Grant) Cheschi of Milford, MA, along with many nieces, nephews, cousins, and several aunts.

David was the brother of the late Steven E. Cheschi and the late Robert S. Cheschi.

Relatives and friends are invited to extend their condolences to his family at the Edwards Memorial Funeral Home, 44 Congress Street, Milford, MA on a DAY & TIME TO BE ANNOUNCED.