Our sweet mystery of life, Josephine Montgomery Gregg, passed away peacefully on Feb. 23, 2020. She will always be remembered as a person who saw the bright side in every situation. While she projected an aura of lightness and joy, Jo possessed incredible leadership skills and administrative savvy. She was a founding member and president of the Skaneateles Cooperative Nursery School, president of the Skaneateles Garden Club and president of the Confraternity of Christian Mothers of St. Mary’s of the Lake Church. She was president of the Austin Park Development Fund and, in the mid 1960s, Jo developed and participated in the successful annual fundraiser known as “Skane-E-Antics,” which featured humorous performances by dozens of residents each year. She was a founding member and later president of the Skaneateles Unit of the Syracuse Symphony Guild, president of the Syracuse Symphony Guild and president of the board of the Opera Theatre of Syracuse. Jo built the annual “Polo for Opera” event, which was held throughout the 1980s and 90s.
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 U.S. 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, N.Y. 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.
A celebration of Jo’s life will be held on May 2, 2020, at 11 a.m. at Saint Mary’s of the Lake Church in Skaneateles. In lieu of flowers please consider a donation to the Leukemia and 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.
