The Dismal Swamp, a densely wooded swamp, covered over 2,000 square miles in southeastern Virginia and northeastern North Carolina between Chesapeake Bay and Albemarle Sound. It is geologically unusual in that it is higher than the surrounding land, and water drains out of it rather than into it.

In 1763 GW and several partners including Fielding Lewis and Burwell Bassett formed a company, “Adventurers for Draining the Dismal Swamp”. They constructed canals and causeways through the swamp allowing for lumber to be harvested while the swamp was draining and to farm the land once it became dry.