She was the first woman to receive the Skaneateles Jaycees Award and awarded “Citizen of the Year” by the Skaneateles Chamber of Commerce. The Junior League of Syracuse gave her a Lifetime Achievement Award and the Cultural Resources Council honored her with their Service to the Arts Award.
She was the broker/owner of a successful residential real estate firm, based in Skaneateles, for more than three decades.
Jo, the youngest of three children, was born on June 6, 1925 in Atlantic City NJ. Her father, Harold B. Montgomery, was the general manager of the renowned Traymore Hotel until the Great Depression struck. Jo never forgot how her mother, Leonide Dagit Montgomery, picked up the pieces of their shattered lives and provided for the family. Her mother’s drive and determination inspired Jo in many ways through the challenging times in her life.
Jo’s husband, Holland C. Gregg II, was enlisted in the US Army Air Force and stationed in Atlantic City and, during World War II, Jo, her sister and her mother participated in USO dance parties, where Jo and Holly met. They married in 1946 and moved to Holly’s hometown of Ithaca, NY. Shortly thereafter they relocated to Syracuse where Jo would meet many life-long friends. She and her family, including three children, moved to Skaneateles in 1957. The New Year’s Eve parties at the Gregg household over three decades were the stuff of legend.
She and Holly were avid skiers and were founding members of the Skaneateles Ski Club. Jo loved playing golf and tennis in Skaneateles and in Vero Beach, FL where, in their later years, she and Holly spent their winter months.
Jo is predeceased by her husband and her grandson, Holland C. Gregg IV, and longtime friend, William Livingston. She is survived by her three children, Leonide (Bob) Connelly, Holland (Patience) Gregg, and James (Emily) Gregg. She is also survived by her grandchildren Christopher (Adelaide) Connelly, Beth Connelly, Jonathan Connelly (fiancé Dena Copani), Marietta (Thomas) Bolster, JJ Gregg and Keely Gregg. She adored her great grandchildren Sean Connelly, JP Connelly, Quinn Connelly, Avery Bolster, Benjamin Bolster, Luna Bolster and Nova Bolster, Griffin Connelly, Keegan Connelly and Sam Copani.
The celebration of Jo’s life on May 2nd has been postponed to a later date. In lieu of flowers please consider a donation to the Leukemia & Lymphoma Society’s Holland C. Gregg IV Research Fund, c/o Marietta Bolster, 47 East Lake Road, Skaneateles, NY 13152.
To send condolences, visit robertdgrayfuneralhome.com.