John I. (Jack) Caldwell III passed away on Tuesday, April 18, 2023, in his home in Bavon, Va., surrounded by his family. He was vibrant and healthy only two months ago, but surgery and a long hospital stay eventually took its toll. Jack wanted to be home in his last days, so his family obliged. He was able to enjoy his fabulous view and see the sunrise over the Chesapeake Bay with a smile on his beautiful face. Jack was born in Meadville, Penn., and spent his teenage years in Pompano Beach, Fla., where he met his future wife, Louise Loftus, through mutual friends. In August of 1965, they were married and spent nearly 58 wonderful years together. Jack worked in the architectural field but also built two of his own homes almost entirely by himself. Just for fun, Jack and Louise sailed their boat (Celtic Knots), paddled their kayaks, rode their bikes, took classes at the gym, traveled extensively, and loved every minute of it. Jack was a kind, generous, warm-hearted man who was delightfully goofy and happy-go-lucky always. He is survived by his wife, Louise Caldwell; his daughters, Eileen Hubbard (Johnathan) and Denise Hood (Mike); granddaughters, Kelly Grubb (Seth) and Annabelle Needham (Josh), and great-grandchildren, Eleanor and Eddison Grubb. A funeral mass was held at Francis de Sales Catholic Church in Mathews on Wednesday, April 26, 2023, at 11 a.m., followed by a reception at Mathews Yacht Club. In lieu of flowers, the family asks that you send donations to Hands Across Mathews either monetary (mailed to P.O. Box 1303, Mathews, Va. 23109) or clothing, food, etc., taken to their physical location at 10878 Buckley Hall Road, Mathews, Va. 23109.

Faulkner Funeral Homes, Foster-Faulkner Chapel, Mathews, is assisting the family.