In Memory of

Cheryl

Ann

Penna

(Barile)

Obituary for Cheryl Ann Penna (Barile)

Cheryl Ann Barile Penna, 59, of Washington, passed away on April 14, 2021 after a two-year battle with metastatic breast cancer.

Cheryl was born on June 25, 1961 to Thomas Jr. and Joan Barile of Pittsfield. After graduating from Taconic High School in 1979, she went on to major in education at Westfield State University.

After graduation, she worked briefly at Lenox Memorial Middle & High School before accepting a position at the Berkshire County District Attorney’s office. Cheryl worked as a victim witness advocate and a youth leadership and prevention specialist for over 20 years until retiring in 2019. Throughout her career, she was passionate in both of these roles at the DA’s office. She loved going to work and helping to shape the lives of Berkshire County’s youth every day.

In 1985 she met James Penna and they wed on August 22, 1987. Cheryl and James went on to have one son, Michael Penna.

When Cheryl had Michael, in addition to excelling at her work, she decided to dedicate her life to excelling as an amazing mother. Cheryl was a rock for her family. Her strength and love guided them through the good times and the bad. Whether supporting James through the loss of his parents or helping Michael get through medical school, she made it her mission to improve the lives of her loved ones.

Cheryl was an excellent cook and loved to entertain. When she wasn’t filling her home with warmth and love, she could be found covered in topsoil in one of her many gardens. We will miss her greatly.

Cheryl was predeceased by her father, Thomas Barile Jr. She is survived by her mother, Joan Allegrone (Louis); her husband, James Penna; her son, Michael Penna; Michael’s fiancé, Olivia Napoli; and her siblings Thomas Barile III (Linda), Kathy Pelkey (Edward), and Joan Barile.

FUNERAL NOTICE: A Liturgy of Christian Burial will be held, MONDAY, April 19, 2021 at 9:00 a.m. at St. Mark’s Church in Pittsfield. Entombment will follow at St. Michael the Archangel Mausoleum in St. Joseph’s Cemetery. Calling hours will be held, SUNDAY, April 18, 2021 from 2:00 p.m. to 5:00 p.m. at DERY FUNERAL HOME, 54 Bradford St, Pittsfield. In lieu of flowers, the family requests that all donations be sent to the charity of your choosing in Cheryl’s name.