Joseph A. Oslander Jr.

Joseph A. Oslander, Jr., a lifelong resident of Madison, Connecticut, passed away peacefully on March 27, 2026, surrounded by family. Joe was the son of the late Joseph A. Oslander, Sr. and Marion (Hilgert) Oslander. He was predeceased by his beloved wife, Florence (Boryszewski) Oslander, and his sister, Arlene O. DuBiago.

Joe is survived by his children: Sepherson Landers (né JP Oslander) and his lifelong partner Jim Hester, of Farmers Branch, Texas; and Suzanne M. Oslander of Newington; along with her longtime friend Thomas Ronalter, of New Britain. He is also survived by his brother, Donald M. Oslander, and his wife Noreen of Madison; his sister, Evelyn O. Barnes, and her husband William, of Niantic; his brother-in-law, Nicholas DuBiago of Worcester, Massachusetts; and his sister-in-law, Linda Sadler of Reno, Nevada, as well as many extended family members and friends.

A graduate of Daniel Hand High School, Joe attended the University of Connecticut, where he received a B.A. in History. He continued at Southern Connecticut State College, where he attained a M.A. in History and a Sixth Year Diploma.

He began his teaching career at Sheridan Middle School in New Haven before returning to serve the community of Madison at Daniel Hand High School. Over the course of his career, he served as a social studies teacher, department coordinator, assistant principal, and principal, shaping generations of students and faculty through his leadership, integrity, and commitment to education.

Joe lived a life rooted in family, learning, service, and nature. Joe’s love for the outdoors began as a child living on the family farm in the Rockland section of North Madison. It continued as he worked seasonally for more than twenty years at Chatfield Hollow State Park. It was there that he met Florence, his best friend and wife of 58 years.

A deep sense of community service for his hometown was at the core of Joe’s life. As a young family man, he joined the North Madison Volunteer Fire Company, later serving as President and becoming a life member. His interest in Madison’s history led him to serve as sexton of Rockland Cemetery and Indian Cemetery and later to become a charter member of the Charlotte Evarts Archives.

Joe considered the creation of Rockland Preserve as a crowning achievement for the Town of Madison. His membership on the study committee to establish Rockland Preserve was followed by his chairmanship of the Rockland Preserve Advisory Committee. He also served on the Madison Land Conservation Trust, the Representative Policy Board of the South Central Regional Water Authority, and the Madison Youth Services Board.

Joe enjoyed cycling, birding, traveling, and nature. He found great joy in being a lifelong learner and teacher. In retirement, his passion for teaching continued, especially when leading hikes and educating Madison third graders about the intricate process of charcoal making at Rockland Preserve. A man of character, intellect, and kindness, Joe will be remembered for his dedication to his family, students, and community.

Joe’s family wishes to thank the wonderful caregivers at Middlesex Hospital, Jerome Home, and The Hospital of Central Connecticut, with special thanks to the North Madison Volunteer Fire Company and Madison Emergency Medical Services.

A Celebration of Life will be held Friday, June 12th, at 1:00 p.m. at the North Madison Congregational Church. In lieu of flowers, memorial donations may be made to the Friends of Rockland Preserve Fund in care of The Madison Foundation or the Madison Land Conservation Trust.