Dover-Foxcroft, Maine - Jefferson "Skip" Leon Prestridge Jr., 82, passed away January 13, 2026, at Massachusetts General Hospital in Boston with family by his side. Born November 1, 1943, in Brewer, Maine, he was the eldest son of Effie Mae (McGray) and Jefferson Leon Prestridge Sr.

In 1961, he earned his high school diploma from RHAM High School in Hebron, Connecticut. Jefferson went by the nickname "Skipper" or "Skip" by friends and family. Aptly named and following in his father's footsteps, Jefferson served honorably in the U.S. Navy from 1962 to 1968. During that time, he attended the United States Naval Academy (USNA, Class of 1968) and served aboard the USS Kittiwake (ASR-13) during the Cuban Blockade. Upon leaving the Navy, he started a family and earned a master's degree in education. A dedicated educator for 36 years (1969-2005), he served his communities as a teacher for children with special needs, and as a ninth grade English teacher and football coach, eventually moving into administrative roles. As principal at the Charleston Mountain View Correctional Facility, he built a therapeutic education program for youth that became a model nationwide. He particularly enjoyed recalling representing the teacher's union in Hampden in the 1970s, telling the story of picketing with his family to ensure that the teachers' voices could be heard.

Throughout his life, he expressed unwavering pride and passion for learning and teaching. He taught his children how to change the oil, replace a flat tire, do a layup, build a bookcase, tighten bolts without over torquing, and what a triple play is. He also instilled in them a love of reading, poetry, and literature, including how to properly recite a poem. Jefferson decided that in retirement he needed something to keep him busy, so he built a "camp" up at the lake - a two-story, two-bath cabin for everyone in the family to enjoy. He could be spotted landscaping his yard and that of the Dover-Foxcroft Library with his dog by his side. Jefferson was a loving husband and father. He was extremely supportive of all of the women in his life, encouraging them in their education and careers, and offering advice, support, and mentoring.

Jefferson is survived by his wife, Lori (Perrigo) Prestridge; daughters, Dr. Katherine Prestridge and her husband, Ben Sims, Kristen Murphy and her husband, Brenden, their mother, Marcia (Trotta) Prestridge, and Catherine Carpenter; stepchildren, Major Stephanie Hasenfus and her husband, Lieutenant Colonel Alex Brubaker, and Nikolaus Hasenfus; sister, Nina Zahacefski and her husband, Ronald; and several nieces, nephews, and grandchildren. He was predeceased by his parents; and his brother, Tommy Prestridge.

A graveside memorial service with military honors will be held at 1 p.m. Friday, May 22, 2026, at Puddledock Cemetery, 169 Puddledock Rd., Charleston, ME. Arrangements are in the care of Lary Funeral Home. Jefferson loved a good story, so if you have one, don't hold back. The family would love to hear it. In lieu of flowers, donations may be made to adoptaclassroom.org in his honor. Messages of condolence and memories may be expressed at laryfuneralhome.com.