Robert McLain Hawkridge Jr. “Lain”, was born on May 12, 1958 in West Chester, Pennsylvania. He attended St. Andrews Academy and St. James Academy. He graduated from Washington College in 1980, returned to Kent County in 1987 and never left. He worked for UPS and received his Master’s in Education from Widener University.

His career as a teacher included teaching in the Baltimore City and Kent County Public Schools before joining the faculty of Radcliffe Creek School, where he was an Orton-Gillingham teacher for 10 years. He retired from teaching to care for his parents, Robert McLain Hawkridge and Sally Middleton Hawkridge, who both predeceased him. During this time he tutored and coached people with learning disabilities primarily through Washington College and Bowman Educational Services/LINKZ.

Lain married Arlene F. Lee, his college sweetheart, in 1984 and again in 1999. He is survived by his wife and two sons, Ian McLain Hawkridge and Jennings Lee Hawkridge, and Ian’s partner, Sarah Bradham; his sister, Sally Hawkridge and nephew, Tim Beken; his godsons, Will Wood and Art Mason; and, his many beloved Middleton and Hawkridge cousins.

During his time as a UPS delivery driver Lain marched in the 1997 Teamster’s National Strike, an expression of a lifelong passion for economic, social, and racial justice. In recent years he became a founding member of the Social Action Committee for Racial Justice in Kent County. He was a primary organizer of the SACRJ food delivery program during the Covid-19 pandemic, extending vital food aid to schoolchildren and seniors in need during the shutdown of regular services. He personally delivered food to the seniors in the Baywood community, whom he came to call his friends.

Lain Hawkridge was deeply committed to family, community, young people, and equality for all. He loved chess, music, history, wine, scotch, and books of all kinds. Lain never missed a wine tasting at the Imperial and, later, he could be found discovering new scotches at the Retriever. He was a dedicated member of Lani Parks’ book club. Lain started an after school Scholastic Chess club with Michael Harvey that taught students in every Kent County school. He was devoted to his Library Chess program every Wednesday afternoon and the Thursday Night Chestertown Chess Club. For years he played chess at the Tea Party festival as Ben Franklin and served as a Tea Party Festival Committee member. He made many friends in his journeys throughout the county, including during his weekly trips to the Chestertown Farmer’s Market.

His fascination with music began as a child in the Holy Trinity Church choir and was evident every Thursday night during his Musicology Show on WKHS. He spent hours each week preparing to share his love for different artists and genres of music with his listeners. But he loved WKHS mostly for the opportunity to work with KHS students like “Johnny Rocker” and his fellow adult DJs. His most recent contribution to Kent County’s music scene was his work as board member for the Chestertown Jazz Festival.

Due to the COVID-19 pandemic, services will be private for family members. The family requests those who wish to express sympathy consider making a donation to the Social Action Committee for Racial Justice in Lain Hawkridge’s name.