PITTSFIELD, Mass. —  

Jonathan Joseph Kellogg, 42 of Pittsfield, passed away peacefully on October 29, 2026, surrounded by his loving family and friends after a courageous battle with cancer.

He was born in North Adams, MA on September 23, 1984 to John and Mechelle LeBeau Kellogg. Jon was a 2003 graduate of Hoosac Valley High School, a 2008 graduate of American International College, where he played football for the Yellow Jackets, creating lasting friendships and memories both on and off the field. He later received his Masters of Business Administration from Cambridge College.

He married the love of his life, the former Ashley Collins on February 26, 2016.

Jonathan dedicated his entire professional career to Hillcrest Educational Centers. He held many positions along the way to becoming the Director of Development and Community Relations.

A diehard University of Michigan fan, Jon even had named his beloved dogs, Michigan and Maize, in honor of the team. He took great pride in maintaining his and Mike Phillips lawn, even resulting in him being initiated into the immaculate lawn club in the neighborhood. He enjoyed the many rounds of golf he played over the years at Berkshire Hills, coaching his daughter Mila’s soccer team, spending time with his loved ones in his pool, but most of all, being a girl dad.

Jonathan is survived by his loving wife of 10 years, Ashley Kellogg of Pittsfield. Their beloved daughter, Mila Collins Kellogg of Pittsfield. His parents, John and Mechelle Kellogg of Cheshire; sister, Shelley Kellogg and children Hannah and Aiden Pringle of Cheshire and brother, Matthew Kellogg of Pittsfield. His in-laws, Gary and Irene Collins of Pittsfield and sister in-law, Lindsay Collins, Matthew Vaughan and son Mason of Pittsfield. Jonathan also leaves a large group of close friends who he loved like family.

A very special thank you to his medical team, Dr. Michael Wagner of Dana Farber, Dr. Margaret Connolly of Brigham and Women’s, Dr. Trevor Bayliss and Brittany Slater, RN, of Phelps Cancer Center as well as Julie Thurston and the team at HospiceCare in the Berkshires.

FUNERAL NOTICE: Calling hours will be held Sunday, November 8, 2026 from 2 to 5 PM at Dery Funeral Home, 54 Bradford St, Pittsfield.

Jon had a unique perspective on life and death, and he felt strongly that when his time on earth was complete, he wouldn't simply be passing away — he would be receiving a well-deserved promotion to heaven. And in true Jon fashion, a promotion of that magnitude deserved a party.

Per Jon’s wishes, a “Promotion Party” will be held Monday, November 9, 2026 at 11 AM at Pittsfield Country Club, 639 South St, Pittsfield.

In lieu of flowers memorial donations may be made payable to Ashley Kellogg for Mila’s college education fund and mailed to Dery Funeral Home.