Philip A. Calabro, 89, passed away February 24, 2022 at the Guthrie Cortland Medical Center. He was born February 14, 1933 the son of the late Frances and Christopher Calabro in Cortland where he lived his entire life. Philip was a graduate of Cortland High School. He was a proud veteran of the US Airforce as a member of the Airforce Band and Orchestra. He attended Ithaca College before purchasing City Delivery. During the 1970's Philip was co-proprietor of Cuzins 3 a bar/tavern with his brother Joe and cousin Phil Natoli. Later he and his son Chris bought the Dryden Hotel in 1986 and became part of that community. His memberships included the Cortland Kiwanis club serving as former president, Knights of Columbus "the Fourth Degree", Homer American Legion ,and Homer Elks. In 1960 he married the former Shirley Nichols who survives him after 62 years of marriage and raised five children together; Karen (John) Shirley, Christopher (Christine) Calabro, Matthew Calabro, Margaret (Linc) Swedrock, and Robert (Katie) Ryder, his grandchildren Sara (Jeff Stark) Shirley, Lauren Shirley, Jake Calabro, Carley Calabro, Camryn Calabro, Ty Calabro, Jackson Ryder, and Nora Ryder, along with many nieces, nephews, and cousins. He was predeceased by his parents along with brother Joseph and his sister Angeline. A Mass of Christian Burial will be celebrated 10:30 am Monday February 28, 2022 at St. Mary's Church, Cortland NY. A private burial will be at St. Mary's Cemetery Cortland at a later time. There are no calling hours. In lieu of flowers contributions may be made to the Cortland High School, “Music Booster Club”, 8 Valley View Dr., Cortland NY, 13045 or St. Mary’s School, 61 N. Main St., Cortland NY, 13045.