Cole Allsopp grew up racing dinghies and keel boats in Annapolis. He attended primarily the Severn Sailing Association Junior Program as well as the AYC Junior program. He went on to sail at the Key School and eventually the College of Charleston where he was captain of the sailing team his junior year. Cole was the Junior Sailing Program Director at Severn Sailing Association from 2012 to 2015 until moving to a career outside of the sailing industry. He is still an active part of the Annapolis sailing community. He lives locally with his wife Liz and two children Vivien and Remy.