The native people of the Chesapeake relied heavily on the canoe as their primary means of transportation. The most common canoe was the dugout , made from the trunk of a large, straight tree. These canoes could be quite large, up to 45 ft long and 3 ft deep, and could carry up to 40 people. They were not very maneuverable, and paddling them was very hard work, but they were highly valued by the indians both because of their usefulness and the difficulty of their manufacture.

Once a good tree was located, it would be felled by burning a fire at its base and chopping with stone axes, then floated back home. The log was shaped by building small fires on the surface of the log and then scraping away the charred wood with oyster shells. Mud was packed on the edges of the log to limit the extent of the burning. This laborious process of burning and scraping would be repeated until the trunk was hollowed out and the bottom flattened to make the canoe stable in the water.

Birch-bark canoes were sometimes seen on the Chesapeake in the hands of the Massawomeck, who lived farther north where the bark needed for canoe making was available. These canoes were faster and more manueverable than the dugouts and were used by the Massawomeck to conduct very effective raids that were greatly feared by the Chesapeake people.