The Herring Island Sailing Fleet, affiliated with Miles River Yacht Club, races sailboats on and around the Miles River. The fleet holds over 20 races a year, ranging from 5 to 20 miles in length. They host a series race for boats with spinnakers, and a more casual race for boats with just jib and mainsails. The fleet website also offers a crewfinder option, and matches crews with skippers.