Kathleen Anne O'Connor

Hampton – Dr. Kathleen Anne O’Connor, formerly of Woburn, passed away peacefully on Friday February 14, 2025. She was 78 years old. Born on August 8th, 1946, to John and Agnes (Bridget Egan) Conway in Boston, Massachusetts, Kathy was proudly raised in West Roxbury within the Holy Name Parish. A brilliant, curious, and sassy young lady, Kathy knew she wanted to pursue a career in service to others. Teaching would become Kathy’s vocation, positively changing the lives of countless students, parents, teachers, and administrators along the way. Kathy was the first lay and female teacher at Boston College High School. She would go on to teach at Woburn High School, Mt. Alvernia Academy, and Boston College. Before retirement and focusing on caring for her husband, Oakie, Kathy spent 10 years as the Director of Lowell Teacher Academy (LPS’s Induction and Mentoring Program) instilling her passion for education in the lives and hearts of the younger generation of educators. Kathy met her long-time soul mate, William “Oakie” O’Connor in the late 1960s at a party of mutual friends. They immediately hit it off with similar humor and passion for teaching. They would marry at Holy Name Parish on July 18, 1970 and would spend the rest of their married life together in Woburn, Massachusetts. Shortly after starting her career at Boston College High School, Kathy made the decision to take time away and start a family with Oakie. The couple welcomed Patrick John to the world in 1971 followed by Caitlin Ann in 1977. Kathy took on the critical role of mother to Patrick and Caitlin but also the role of Mrs. O’Connor, tutoring local children and relatives, while also supporting nearly 4 decades of Coach O’Connors athletes, counseling them on college, applications, and scholarships. Many of those students she tutored and mentored would go on to illustrious college, athletic, and professional careers. It was only when Caitlin was in grade school that Kathy would continue her career as a teacher and administrator for the next 30+ years. Kathy was a lifelong student and educator. She was a graduate of Framingham State University, majoring in History and Education. She would go on to receive her Master’s Degree in American Studies and PhD in Curriculum and Instruction from Boston College. Family was important to Kathy. Being present and supportive both academically and athletically was of utmost priority. Kathy’s high-pitched squeal at indoor tracks cheering on each Algonquin, Woburn, UNH, or Bowdoin athlete was a staple at any meet. Kathy, not herself a runner, had the amazing ability to make it from one end of Franklin Park (Boston) to another screaming and waving her arms for her cross-country family as she would somehow make it to the finish line before them. Kathy would often put Oakie and her children’s needs before her own. She would forgo tropical vacations for indoor track meets, date nights for community fun-runs, and lavish gifts for game nights and movies with the family. Her and Oakie’s most cherished time together was the week or two they would spend each summer on Cape Cod. Whether it was Dennisport, Harwich, or Chatham this was their happiest place to be. Kathy loved the beach and the ocean. She loved the smell of the salty air and the friends she would spend time with while watching her children grow and create their own memories. Their favorite spots were Fenway Beach, Chatham Bars Inn beachside, and the Wild Goose Tavern (preferably by the piano). It is clear to see that Kathy was every bit a Leo. A passionate teacher, a leader in education, a friend to many, and an endless love to Oakie and her family. She was proud and courageous. She was selfless but sassy. She was hilarious yet proper. She did her best to hide the Lewy Body Dementia that would ultimately take her mind and body. Until her last breath, she had the smirk, the wink, and the wit. It only seemed appropriate that Kathy would be reunited with Oakie, who passed away in 2016 from cancer, on Valentine’s Day. Being the hopeless romantic, Oakie wanted his best girl back in his arms. Kathleen is survived by her children Patrick O’Connor and his wife Jennifer of Weymouth, MA, Caitlin Baldwin and husband Matthew of Exeter, NH along with her two grandchildren Jake and Ryan. In addition to her husband William, Kathleen is predeceased by her parents John and Agnes (Bridget Egan), Conway and her brother John Conway. In keeping with Kathleen’s wishes, a private celebration of life will take place on the Cape this summer where her and Oakie’s ashes will be spread together in their favorite spots. In lieu of flowers, please consider a donation in Kathleen’s memory to the two charities that meant the most to her, the Southern Poverty Law Center or the ACLU.

Kathleen Anne O'Connor

August 8, 1946 - February 14, 2025