WINDHAM - James Howland of Windham, passed away peacefully on May 3, 2020 while in hospice care. Mr. Howland was born on March 27, 1964 in Boston, Massachusetts to the late Dorothea E. and Harrison C. Howland. He was raised and educated in Stoughton and West Bridgewater. As the youngest child, Jamie always strived to keep up with his brothers, especially in sports. In 1984 he moved to Maine. He worked for D'Angelo's and J Brothers, both family businesses. He had a strong sense of family and was a steadfast son to his parents, visiting them often and keeping in touch by phone and thoughtful correspondence. He enjoyed taking drives to visit his Maine siblings and would arrive with his ever present headset on, lost in his music. He would often call just to check in with family members concerned for their well being. He was loved for his kind heart and sense of humor and will be missed by his siblings and their spouses: Jay and Ingrid Howland, Jon and Sandy Howland, Janis and Gary Erickson, Jill and Robert Wallace, Jeff and Dawn. Howland, and Jerry and Denise Howland. He also leaves behind his partner Angela L. Penek. In addition he is survived by numerous nieces, nephews, cousins, aunts and uncles. A family gathering will be scheduled at a later time to share memories and honor his life.