Obituary: Winifred 'Winkie' Schaefer Chesley, 89, Of Wilton

Information and Photo Courtesy Bouton Funeral Home

WILTON, CT — Winifred “Winkie” Schaefer Chesley, 89, completed her earthly life suddenly, on Wednesday, Feb. 28, 2024. Prior to having had spent her last five years in Redding, she was a resident of Wilton for over 50 years.

Born Sept. 14, 1934 in New York, NY, she was the daughter of the late Frederick Maximillian Emile Schaefer and Helene Goldsmith Schaefer, and spent her childhood in Larchmont, NY, where Winkie developed her love of the sea. Some of her fondest memories were of sailing and fishing with her father. Ocean water grounded her, and in her later years she could be found beachside daily, walking her beloved dogs.

Winkie and her late husband, Willoughby F. Chesley, Sr, raised six children in Birmingham, MI; Bay Village, OH; and then Wilton.

Never idle, when her children were younger, with patterns spread all over the floor, she could always be found at a sewing machine making the kids’ clothes and repairing costumes. In the kitchen, she would single-handedly put on the traditional Sunday dinners; and, she was forever making carrot bread for others. Each evening, she had knitting needles in hand, creating intricately patterned sweaters, mittens and hats.

She was always highly invested in her communities, volunteering and serving with numerous charities. She was the longtime bookkeeper for the non-profit Wilton Community Assistance Fund (previously named Wilton Interfaith Council). She served as an EMT with the Wilton Ambulance Corps, and was a hospice provider with Fairfield County Hospice, having deep-felt love and respect for patients with AIDS. In addition, Winkie volunteered numerous hours with Meals On Wheels, Minks-to-Sinks, and Stay at Home Wilton.

Combining her passion for gardening and her drive to give of herself, she volunteered 40 years of service to the Saint Matthew’s Episcopal Church, overseeing all aspects of the parish cemetery. She was responsible for the burial scheduling, site prep, working with families, and the cemetery record keeping. Not only did she oversee the grounds upkeep, she performed a good deal of physical maintenance herself, hauling jugs of water and potting soil. Winkie was taken by complete surprise several years ago, when the church erected a memorial bench in her honor.
Winkie’s need to always be giving of her time made a huge impact on her grandchildren, as she was fiercely devoted to fulfilling their needs with her time, talent and treasures.

She had a generous spirit, offering room and board to recovering alcoholics, and those experiencing other challenging chapters of life. She loved giving surprise gifts to anyone and everyone.

Winkie was a role model as how to age with vitality and purpose. She had infectious energy. Winkie trained long hours walking the hills of Wilton, with a rock weighted backpack strapped to her, training for a hike in the Alps. She accomplished her mission 6 months later, spending the nights in hostels. She was 56 years old at the time.

She is survived by her sister Frederica H. Schaefer; six children; eleven grandchildren; five great-grandchildren; and two step-grandchildren.

Memorial contributions may be made to either: Saint Matthew’s Parish Cemetery, c/o Saint Matthew’s Episcopal Church, 36 New Canaan Road, Wilton, CT 06897; or, to Wilton Community Assistance Fund, 180 School Road, Wilton, CT 06897.

Arrangements are being posted by Bouton Funeral Home, Georgetown, CT.

Condolence messages can be sent to: www.boutonfuneralhome.com

Celebration of Life gathering is Monday, March 11, 2024, 2-4 p.m., at Meadow Ridge Senior Living, 100 Redding Road, Redding. Open to family and friends.