Breckinridge was also concerned with easing overland transport of goods to Virginia. In mid-1795, he, Robert Barr, Elijah Craig, and Harry Toulmin formed a committee to raise funds for a road connecting the Cumberland Gap to central Kentucky. Breckinridge was disappointed with the quality of the route, which was finished in late 1796, concluding that the individual maintaining it was keeping most of the tolls instead of using them for the road's upkeep.