Alan Roy Osgood Sr., 64, of Pownal, VT, passed away on January 4, 2024, at his home surrounded by his family. Alan was born in Troy, New York, on August 16, 1959, the son of Matthew and Della (Prue) Osgood. He was married to the former Cherie Belville. Alan was an accomplished wrestler in his earlier days. He spent a large portion of his working life as an auto mechanic, working for several different garages and dealerships in the area. He loved working on and rebuilding older cars. He also enjoyed fishing. He loved his miniature dachshunds, Minimin and Precious. Alan is survived by his wife of over 40 years, Cherie Osgood, of Pownal; his children, Edward Belville of Pownal, VT, Karen Osgood and her husband, Matt Wright of Pownal, VT, , and Alan “AJ” Osgood, Jr., also of Pownal, his brothers and sister; Stanton Osgood of Maynardville, TN, Chuckie Osgood of Pownal, VT, Jeffrey Osgood of Maynardville, TN, Donald Osgood of Bennington, VT and Karen Greene of Shaftsbury, VT. He is also survived by his grandchildren, Austin Belville, Isiah Belville-King, Amiah Belville-King, Amarah Osgood, Brody Osgood and Jaxtyn Morse, his dear friends, Andy and Shirley Martin, Terri Smith, Mark Dufresne, Joe Walsh, James Harley, Laura and Richard Muir, Robert, and Arlee Yeardon, Pearl and Bruce Burbee and many more nieces, nephews and friends. The family will receive friends at the Mahar Funeral Home, 628 Main Street Bennington, VT, on Friday, January 19, 2024, from 5:00 PM to 7:00 PM.