Robert "Bobby" Stephenson grew up in Kent County, Delaware, and attended Lynchburg College in Lynchburg, Virginia, where he earned a Bachelor of History in 2008. After earning his Masters degree in American History from James Madison University in 2010, Bobby accepted his first teaching position at Valwood School in Valdosta, Georgia, where he taught an assortment of Social Studies classes and served as History department chair from 2010-2018. In the summer of 2018, Bobby and his wife Heather moved to the Eastern Shore where Heather took a position as a Physical Education teacher at Country School in Easton and Bobby joined the History department at The Gunston School. In addition to teaching U.S. History, Bobby advises the Mock Trial Club, serves as Students Activities Coordinator, and coaches the Varsity Cross Country team. Bobby and his wife, Heather, have a young son, Lane, a proud member of the Gunston class of 2034! In his spare time, Bobby loves to spend time with his family, hiking, biking, camping, and kayaking, and his favorite book is A Walk in the Woods by Bill Bryson.

Bobby Stephenson Named ESIAC Coach of the Year