Obituary: Jeffrey D. Caldwell, Sr.

Jeffrey D. Caldwell, Sr. age 74 of Orange entered into rest on Friday, March 4, 2022 at his home with his loving family by his side.
He was the devoted husband of almost 50 years to Candice (Smith) Caldwell. Jeff was born in New Haven on March 6, 1947, son of the late Theodore Carter Caldwell, Sr. and Helen (Taylor) Caldwell and was an Orange resident for most of his life.
Jeff was a kind and gentle man who lived a full life that some would compare to Forest Gump. As a child, he grew up in Stockbridge, MA, home of Norman Rockwell. He and his friends would find Norman’s dog wandering around the town, return him, where Mr. Rockwell would give them $5 which he and his friends would use to buy candy. As he grew up in Stockbridge, he got to know all the real life characters from the Arlo Guthrie song “Alice’s Restaurant”. Stockbridge is also home to Mohawk Lake, where Jeff got to play hockey with several characters from the movie Slap Shot. Jeff then moved to Orange, CT where he graduated from Amity Sr. High, then enlisted in the USAF. It was in the Air Force where Jeff had the opportunity to travel the country, world, and even shake the hand of President Johnson. After his brave service to his country, Jeff had the chance to see Queen Elizabeth in New Haven in 1976, the day after having his vasectomy, stating the whole thing was a pain in his….
He proudly served with the US Air Force as a Flight Line Mechanic from 1966 - 1970. Jeff worked for United Technologies for many years until his retirement. He was a car enthusiast and a longtime member of the Shoreline Street Rods Club. Jeff was also an avid billiard player, played hockey, enjoyed horror movies, trips to Mohegan Sun Casino and visiting local dog parks. Jeff was a die-hard fan of the New York Rangers, New York Giants and the Los Angeles Dodgers.
Other enjoyments of Jeff’s life were many swap meets to find parts for the engines he rebuilt, several fun camping adventures in his boyhood town of Stockbridge with family and friends. Later years included his daily ride to the baseball fields to watch the games and check out the Ospreys. Winter would bring him to Wright’s Pond to watch the skaters, some in figure skates but was most interested in hockey, once asking the players to ask a lone skater with his stick and puck to join them. At times he would bring hot chocolate and hand warmers for the skaters.
He was the beloved father of Tiffany Beesley (William) and Jeffrey Caldwell, Jr. (Melanie), loving grandfather of William and Sarah Beesley, and Kyle and Kadin Caldwell and brother-in-law of Lorraine Caldwell. Jeff is also survived by several nieces and nephews. He was predeceased by his brother Theodore Carter Caldwell, Jr.
Friends may call on Wednesday from 4 to 7 PM at the Edward F. Adzima Funeral Home, 253 Elizabeth St., Derby. Masks are required in the funeral home. On Thursday, friends are invited to go directly to Orange Congregational Church, 205 Meetinghouse Lane, Orange for his funeral service at 11 AM. His burial will be private.
The family requests, in lieu of flowers, that memorial contributions may be made to American Lung Association, www.lung.org or American Cancer Society, donate3.cancer.org.
Friends may leave condolences at www.adzimafh.com.