James E. Callahan Jr, of Middlebury, VT, died peacefully surrounded by his wife Karlene and three sons on August 8, 2019. Jim was born January 29, 1936 in Boston, Massachusetts to James and Katherine Callahan. Jim joined the Air Force in 1954 and was stationed in Thule, Greenland. In 1958, he returned and attended Lowell State, followed by earning subsequent degrees from Salem State and Boston University. Upon graduating, he taught elementary mathematics in Burlington and Winchester, Massachusetts before coming to Vermont in 1970 to become the principal of Mary Hogan School in Middlebury until 1983. During his tenure as principal he also taught graduate classes at St Michaels, St Joseph, and Castleton State, as well as coaching boys hockey and teaching Middlebury College students SCUBA diving. In the mid-80s he began his math consulting business which took him all over the county doing math workshops for elementary schools. In his retirement, he enjoyed tutoring local students his favorite subject of math. He dearly loved his family and spending time with them and his special friends. Jim is predeceased by his parents, his son James Callahan III in 1982, and his sister Pat and his brother-in-law George Dow. He is survived by his wife, Karlene, his son Dan and his wife Natalie and their 4 children Jim, Peter, Oni, and Evan of Middlebury, his son Mike and his wife Kate and their daughter Amanda of Dover, NH, and his son Will and his wife Rachel and their three children Brooks, Taea, and Ronan of Essex Jct, and several extended families members all over the country. Visiting hours will be held at the Sanderson-Ducharme Funeral Home on S. Main St in Middlebury on Monday Aug 12th from 4-7. Contributions can be made to St Judes Hospital for Children or Shriners Hospital for Children in his name. Arrangements are under the direction of the Sanderson-Ducharme Funeral Home. Online condolences at www.sandersonfuneralservice.com SERVICES Memorial Service Monday, August 12, 2019 4:00 PM - 7:00 PM Sanderson Funeral Service 117 South Main Street Middlebury, Vermont 05753