CHESHIRE, Mass. —  Steven Ralph Bailey, 62 of Cheshire, MA died Thursday October 15, 2026 at Hillcrest Commons.

He was born in Pittsfield, MA on February 22, 1964, a son of the late Ralph Everett Bailey Jr and Emma A. (Maggioli) Bailey. He graduated from Taconic High School.

Steve was employed with BETNR Construction for many years. Before that, he worked at Quality Auto. He enjoyed playing golf, fishing and watching sports.

Survivors include his sister, Diane Bailey of Pittsfield, MA; his sister in law, Heidi Bailey of Adams, MA; two nephews and one niece including Trevor Bailey, Scott Bailey and Tawnia Hanel. His brother, John J. Bailey died on May 2, 2026. Steve’s family would like to extend a heartfelt “thank you” to the staff of HospiceCare in the Berkshires for their support in his final days.

FUNERAL NOTICE: The funeral for Steven Bailey will be Wednesday October 21, 2026 at 11:00 AM at FLYNN & DAGNOLI-BENCIVENGA FUNERAL HOME, 5 Elm St. Pittsfield, MA. Burial will follow in St. Joseph’s Cemetery. A calling hour will be held Wednesday morning October 21st from 10:00 AM to 11:00 AM. Memorial donations may be made to the American Cancer Society in care of the funeral home. To add to the Book of Memories, please visit www.flynndagnolifuneralhomes.com