Phillip A. Chesky, age 68, passed away peacefully on November 16, 2025 at Baystate Medical Center, with his loving family by his side. Born in Holyoke, he was the son of the late Carl and Evelyn (Gawron) Chesky. Phil served the City of Holyoke for many years as Director of the Parks & Recreation Department and later operated a neighborhood liquor store, forming lasting connections with the community. Above all, Phil took great pride in the life he built with his late wife, Lori (Curran) Chesky, and in the family they raised together. In his early life, Phil overcame cancer, an experience that shaped his appreciation for the everyday joys he loved: summer afternoons by the pool, Red Sox games, swimming at the Y, visits to the beach, playing cards on his porch and cheering on his grandchildren, nieces and nephews or friends from the neighborhood at their sporting events. He especially treasured being a Dziadziu to Colleen, Ben, and Will Chesky, and Saylor, Rory, and Finn Santabarbara. He is survived by his son, Phillip Chesky, and his wife Maureen of Wilbraham; his daughter, Roz Santabarbara, and her husband Gregg of Walpole; his siblings Jeff (Priscilla) Chesky, Kris (Aimi) Chesky, and Carlene (Steve) Hamlin; and many nieces, nephews, cousins and extended family. In recent years, he enjoyed the companionship of Kathleen Magoon, and together they traveled with friends and shared new adventures that brought happiness to his life. Phil will be remembered for his welcoming nature, the easy conversations he struck up with people from all walks of life, and the genuine joy he found in everyday moments. Funeral services will be held Tuesday, November 25, at 11:00 a.m. from Barry J. Farrell Funeral Home, 2049 Northampton Street, Holyoke, followed by a Mass of Christian Burial at 11:30 a.m. at St. Theresa of Lisieux Church, 9 E Parkview Dr, South Hadley. Burial will be at the convenience of the family. Calling hours are Tuesday, 9:00–11:00 a.m. In lieu of flowers, donations may be made in Phil’s memory to the Greater Holyoke YMCA.