Chesapeake also offers a wide selection of kayaking options from the historic Great Dismal Swamp Canal to Lake Drummond, the largest of two natural freshwater lakes in Virginia. Kayaking also takes center stage during the annual Paddle for the Border event (May) and the new Paddle the Peake challenge. Join the adventure when you download the free, mobile app and earn rewards by checking in at nine locations while learning more about the history and ecology of local waterways.