Robert L.P. Montgomery, Jr., 75 of Bennington, VT and Poinciana, Fl., passed away unexpectedly but peacefully at his deer camp in Winhall, VT on November 16, 2025, surrounded by family and friends. Bob was born in Bennington on August 16, 1950, the son of Robert Sr., and Janette Alice (Brown) Montgomery.
Monty was an educator for 34 years, most of which was spent teaching Biology and Earth Science at Mount Anthony Middle School. He also taught at Mount Anthony Union High School for 5 years, was Assistant Principal and Interim Superintendent of the Career Development Center.
He enjoyed hunting, fishing, golfing and shooting trap. He was a member of the Catamount Rotary, also serving on its board, a former member and past president of the Norshaft Lions Club, a member of the Superintendents Association, the Principals Association and a member of the Elks Club for over 30 years.
Monty is survived by his wife, Amy Jo Montgomery, of Bennington, VT and Poinciana, FL, his children; Maegan Morgan of North Hoosick, NY and Robert III (Amira) Montgomery of Leominster, MA, his sister, Gwenn Hannan of Bennington, VT and his grandchildren; Michaela, Declan, Allanah, Noelle, Mina and Ashlee. He was predeceased by his sister Julie Hannan and son Eddie Montgomery.
At his request there will be no formal services. There will be a celebration of life at a later date. Should family and friends desire, contributions in Robert’s memory may be made to Habitat for Humanity through the office of the E.P. Mahar and Son Funeral Home 628 Main Street Bennington, VT 05201.