Heading to the river near Dent's Meadow on the night of April 20, Jones led the fugitives down a steep path to the shore. Here Booth was placed in the stern of a small boat and Herold climbed in to row. Jones gave the pair a proper course to carry them across to Point Mathias, VA and on down to Machodoc Creek and the home of Elizabeth Quesenberry. After paying Jones $18 for the boat, Booth and Herold shoved off.

Rowing out into the stream, the two became disoriented due to difficulties reading the compass and tricky currents in the river. As a result, they missed the tip of Point Mathias and rowed upstream to Blossom Point, MD. At dawn, Herold recognized their location as the mouth of Nanjemoy Creek. In typical dramatic fashion, Booth, in his diary, attributed their navigation error to being chased by Union gunboats. While Union warships were active on the river that night, none reported seeing Booth or Herold. Familiar with the area, he guided Booth to a farm owned by his friend Peregrine Davis. Known as Indian Town, the farm was inhabited by Davis' son-in-law, John J. Hughes. Coming ashore, Hughes fed the men and allowed them to stay through the evening of April 22. At sundown, Booth and Herold departed in a second attempt to cross the river.