The Herring Island Sailing Fleet is a group of dissipated sailors united by a common delusion, to wit: there is an island in the Miles River at the mouth of the Wye River which no one else can see. They make great fanfare of racing sailboats around said non-existent geographical feature.

The Herring Island Sailing Fleet was formed in 1977 by Miles River Yacht Club members who wanted an informal sailboat racing program for cruising style boats. We now conduct nearly 20 races a year on and around the Miles River. The races usually start and end on the Miles in the vicinity of the sunken Herring Island, north of St. Michaels, and range from five to 20 miles in length. The series races are for cruiser/racers sailing with spinnakers and there is a more casual series for boats with just Jib and Mainsails. We also have social events such as picnics, often at a members’ waterside home. Our dinners and social events are legendary.