The log canoe is a type of sailboat developed in the Chesapeake Bay region. Based on the dugout, it was the principal traditional fishing boat of the bay until superseded by the bugeye and the skipjack. However, it is most famous as a racing sailboat, and races continue to be held.

The history of the log canoe is closely tied to the development of the oystering industry on the bay. In pre-power days, the log canoe was an inexpensive craft which could be assembled without recourse to shipbuilders; before the dredge was made legal in 1865, the log canoe was sufficient to the needs of oyster tongers. It did not have the pulling power necessary for dredging, however, its log construction was combined with characteristics of other vessels to form the first bugeyes, a much larger and more powerful vessel. As motor power became available, watermen who were not dredging gradually abandoned sail power; also, the supplies of suitable timber were gradually exhausted. Log canoes were often converted to motor power, and new workboats (such as the Chesapeake Bay deadrise) were motored from the start and used frame construction instead of logs. Many of the existing log canoes have suffered some conversion of this sort during their lifetimes.

Over the same period, however, the ad-hoc racing of canoes evolved into a semi-formal sport, and boats began being purpose-built for racing. From 1885 onward various clubs and associations sponsored organized races. This continues to the present, and racing canoes have been built as recently as 1974.