Douglas G Mccaskey

Douglas Graham McCaskey, 68, of Fairfield, passed away peacefully on September 28, 2023.
Doug was born to Thomas and Mary McCaskey on March 28, 1955, in St. Louis. His family moved to Fairfield, CT, where he would go on to attend Fairfield Ludlowe High School and be an active member in his community. Doug was a tremendous athlete as a young man, having several accomplishments and trophies for football, tennis,sailing and ski teams. He enjoyed teaching and was a certified ski instructor at Otis Ridge Ski Resort.
Doug was a graduate of Babson College, where he obtained his bachelor's degree in three years, was a member of Delta Sigma Pi fraternity, and was only one credit away from obtaining his MBA. He went on to have a successful career working with Reader's Digest, Shearson American Express, and Oppenheimer& Co.
Above all, Doug's passion in life was being out on the water. He was the owner of several different sail and motor boats. He was an accomplished captain, having traveled along the length of the Atlantic Seaboard from the Bahamas to Nantucket, Block Island, Cuttyhunk Island, Martha's Vineyard, and several places in between. He was trusted and joined by many friends and family members for his voyages.
Doug was a devoted and caring father to his two daughters, Isabelle and Mary Grace. He attended every horse show, sporting event, choir concert, and graduation with great pride. He was fun, spontaneous, and often surprised the girls with a trip to Disney World for their February school breaks.
Doug will be dearly missed by his loving family: his wife, Hope Trowbridge McCaskey; his daughters, Isabelle McCaskey (Mark Monteiro), Mary Grace McCaskey, their mother Elizabeth Canavan McCaskey; his siblings, David McCaskey (Laurie McCaskey) and Sandra Webb; and his several nieces and nephews.
Friends and family may visit at the Spear Miller Funeral Home on Thursday, October 5th, from 4:00 o'clock in the afternoon until 5:00. A memorial service will be held in the funeral home immediately following, beginning at 5:00 pm. In lieu of flowers, memorial contributions may be made to the Fairfield Fire Fighters Charitable Foundation, PO Box 261, Fairfield, CT 06824.