Gertrude (Trudy) Gilleland O'Connell

GAINESVILLE, Fla. – Gertrude (Trudy) Gilleland O’Connell, 66, of Gainesville, passed from this world into God’s perfect peace at 3 a.m. on Jan. 27, surrounded by family. She was born in Norfolk, Va., on Nov. 21, 1957, the daughter of the late World War II veteran Thomas Albert Gilleland and Gertrude (Landing) Gilleland. She grew up in the historic riverside Winona neighborhood with her brother Thomas and cousin-more-like-sister Ruth just down the street. It was here that Trudy came to embrace Southern hospitality and discover a lifelong love of being near the water — defining characteristics she would carry throughout the rest of her life. In 1979, Trudy completed her undergraduate studies in education at Old Dominion University and three years later graduated from the College of William & Mary with a Master of Business Administration. On her first day at William & Mary, Trudy met her lifelong love, Mark O’Connell. The nicest girl he ever met, they married Dec. 19, 1982, in a beautiful ceremony in the Wren Chapel at William & Mary — the oldest college building in America. The newlyweds spent their early years in St. Louis then later took up residence in Ocala for 32 years, where they raised three children. During the last three years, they lived in Gainesville only a few blocks away from their daughter, son-in-law and beloved grandsons. Trudy was an endless source of generosity, comfort and warmth to all she knew, the portrait of a Proverbs 31 woman. The O’Connells often opened their home to neighbors, friends and acquaintances for parties featuring Trudy’s signature tablescapes, home-cooked meals and delightful dessert spreads. She was a gifted hostess and homemaker, and her kitchen always smelled of freshly baked cookies. She passed her love for baking on to her children and grandson; her legacy of hospitality and kindness will carry on for generations. Trudy’s soft-spoken and gentle demeanor was contrasted by her sharp sense of humor and terrific wit. Besides baking, she enjoyed restoring their properties on Lake Weir and in Savannah. She loved cross-stitch, travel, antique shops, and especially their Corgi, Jeffers. Trudy was happiest near the water, whether it was found in summer weeks on the remote island of WaWaNosh in Canada; beachside in Captiva; or from Adirondack chairs looking over Lake Weir for a Fourth of July sunset with a yard full of friends, kids and neighbors humming in the background. Throughout all of her days, Trudy trusted in Jesus, delighting in the Lord’s presence and His people. She was active in her children’s schools, home rooms and PTAs, and she made friends everywhere she went. She was a deeply devoted wife, mother, grandmother and friend. Trudy is survived by her husband of 41 years, Mark, of Gainesville, and her children, Dan O’Connell of Ocala; Harris O’Connell and his wife, Miki, of Jackson Hole, Wyo.; Amy Sapp and her husband, Brandon, and their sons, Micah Thomas (3 years) and Nolan Dermot (3 weeks), of Gainesville; and Kayla Castillo and her husband, Randy, and stepson, Mikkel Baker, of Lagrange, Ga.; as well as many other close family members and friends. A celebration of life for Trudy will be held at a later date. In lieu of flowers, donations to Ocala Interfaith Emergency Services and Women’s Pregnancy Center of Ocala may be made in Trudy’s name.

Gertrude (Trudy) Gilleland O'Connell

November 21, 1957 - January 27, 2024