Kenneth "Flapper" Flynn

Kenny "Flapper" Flynn, 79, of Boxford, MA passed away peacefully on August 20, 2025 at the Kaplan Family Hospice House in Danvers, MA with his wife, Ann and daughter, Colleen by his side. Born and raised in Stoneham, MA, Kenny was a proud member of the Stoneham High School Class of 1964. Kenny furthered his education at Salem State University where many lifelong friendships began to develop around the North Shore. Kenny's fondest memories include stories with his great teammates and friends. He routinely noted days at Rec Park, softball games at the Willows, times at the Redmen, and backyard parties on Beacon Street. Kenny's love and pride for his roots were strong. Kenny completed basic training at Fort Leonard Wood, Missouri and became a member of the National Guard. Soon after, his athletic competitiveness, strong work ethic, and charisma translated into a successful career in the automobile business. For over 20 years, Kenny's ability to connect with customers allowed him to dominate in both sales and leasing at Thomas Ford in Beverly, MA. The Ford industry is where he was introduced to his wife, Ann Regan and the two married in 1990. After an early retirement, he found a calling at Black Tie Limousine for 9 years. "Flapper," loved talking with passengers and sharing stories. He thrived covering the early morning trips to Logan Airport to ensure he was on the golf course for an early tee time. Kenny was the ultimate sports junkie. He had a unique ability to connect with anyone he met by stating sports statistics from any area. In addition to knowing sports, Kenny was an esteemed athlete well into adulthood. A member of Haverhill Country Club since 1990, Kenny thoroughly enjoyed the game of golf, but it was Kenny's HCC friendships that were a far greater joy. He loved meals in the 19th hole, being a course ranger, Christmas parties, and the camaraderie with fellow members. Travel was another large part of Kenny's life. The Flynn family explored new places together including Ireland, Italy, England, Costa Rica, and most U.S. states. In addition to vacations, Kenny and Ann spent several winters in Naples, Florida. Kenny was the perfect snowbird: basking in the sun, playing golf, watching Red Sox spring training games and dinners out on the town. No matter where he was Kenny always found time to watch Chuck Connors on "The Rifleman." Family was the center of Kenny's world. Husband to Ann for 34 years, and wonderful father to his daughter, Colleen. Colleen was the proudest gift he ever received in life. The two shared a bond that ran so deep. They loved sports, dancing, listening to rock n roll music in the car, eating ice cream and just spending time together. Kenny made sure to instill the importance of slowing down and enjoying life. Kenny was the very best father, husband, brother, uncle and friend. He was a genuine and caring person with both a big heart and personality. He will truly be missed by many. Kenny is predeceased by his parents Fenton George Flynn and Lois Tyler Longland of Stoneham, MA. Kenny is survived by his wife Ann Regan Flynn of Boxford; his daughter Colleen Flynn; sister Patricia O'Hearn of Boca Raton, FL; and many extended family and close friends. Relatives and friends are respectively invited to attend a Funeral Mass on Tuesday, August 26th at 11:00 AM in Sacred Hearts Church, 165 South Main St. Bradford, MA. Kenny's celebration of life will follow. Interment will be private at the St. James Cemetery at a later date. The Flynn family would like to extend a special recognition and thank you to Dr. Beltran and her team at the Dana Farber Cancer Institute for the outstanding treatments, care and support given to Kenny. Donations are kindly asked to be made to Saint Vincent de Paul Society at Sacred Hearts Parish or Dr. Beltran's Giving Page for Dana Farber Cancer Research. To share a memory or for more information, please visit www.farmerfuneralhomes.com