Stephen Arthur Tole

Stephen Arthur Tole, of Orange, Connecticut passed away peacefully at Bridgeport Hospital, in Bridgeport, Connecticut on April 3, 2024. He was 79.

The second son of nine children, Stephen was born in Cambridge, Massachusetts to Rita Marie (Sweeney) and Arthur Francis Tole on June 6, 1944, a date that gave him much pride and reverence for WWII history. There wasn’t a movie about D-Day that he hadn’t watched, nor a historical fact that he did not know. 

Stephen grew up in Melrose, Massachusetts, where he attended St. Mary’s Elementary School, later moving with his family to New Rochelle, New York. After graduating from Blessed Sacrament High School in New Rochelle, Stephen attended Fordham University in Bronx, New York. He met his wife Mary Camille (Millard) while skiing at Windham Mountain in the Catskills, they married in 1967 and resided first in Bronxville, New York before settling in Darien, Connecticut to raise their two girls.

For over 30 years, Stephen was a devoted employee of Helmsley-Spear Inc., and was General Manager of some of New York City’s most iconic properties; the 15 years he spent overseeing the management of the Empire State Building were his most rewarding. The pride and meticulousness in his stewardship of the famed building garnered many awards but his greatest joy was engaging with the flocks of tourists visiting the building, many of whom he’d graciously whisk out of the long queue and send on an express elevator up to the observation deck. Hundreds of thank you notes from weary and grateful travelers from around the world attest to his kindness and generosity.

Stephen lived a large and gregarious life. He had a flair for the dramatic, loved being in the spotlight, and most of all, loved playing golf with family and friends. He never passed up an opportunity to belt out a pitch-perfect rendition of Danny Boy or Ave Maria, be the Grand Marshal in Tole Family St. Patrick's Day Parades, or regale his golfing buddies with jokes and stories on the 19th hole at his beloved Abenaqui golf club. 

Stephen’s favorite place to be was Rye Beach, New Hampshire where he spent over 75 joyful summers. First, as a child growing up with his siblings, spending long days on the beach, and later with his own family in his cherished cottage by the sea; golfing, tending to his rose bushes, hosting Great Lawn Parties, organizing beach bonfires and grilling big steaks. Here, he was most happy and content, surrounded by the huge extended family he adored.

Stephen is survived by his wife of 56 years, Mary Camille, his two daughters Suzanne Webster and Cynthia Miller, their husbands Steven Webster and Gordon Miller, his five grandchildren Henry, Annabel and Claudia Webster, and Wyatt and Cal Miller. His eight siblings also survive him; Robert Tole (Margaret), Mary Claire Clarkson (Stephen), Karen Borgia (John), Christine McGill, Richard Tole (Martha), Barbara Krant (Ken), Kathy Corbett (Greg) and Paula Tole; as well as his brother-in-law James Millard (Kathleen), sister-in-law Tricia Millard, and twenty-one nieces and nephews.

A funeral mass will be held at St. Pius X Catholic Church in Fairfield, Connecticut on Monday, April 22 at 11:00 a.m. In place of flowers, donations can be made to the National Fragile X Foundation (www.fragilex.org) or FRAXA Research Organization (www.fraxa.org).