Frederick Douglass is rented by a new owner named Mr. Freeland after having been owned by Mr. Auld, a slaveholder from Baltimore. Mr. Freeland owned fields of cotton white as the clouds above. Frederick knew that if he didn’t make an attempt to get to freedom he would not forgive himself. Frederick went to recruiting slaves and recruited John, Henry, and a former friend named Sandy all joined Douglass’s group.
Frederick Douglass and his newly formed gang start planning a way to escape, but kept running into problems. The group becomes discouraged by the low chances against them. They would have to avoid hundreds of scouts that lurked like lions in the woods and even if they did escape they would be liable to being turned in to the south, a certain death sentence. Frederick knew the group could not go to Canada because no one knew much about it. Frederick Douglass tells the group “We will escape, it is the choice between life or death!”
The next day as Frederick is harvesting cotton in the fields he has an idea. That night Frederick gets everyone to tell them the plan, “We are going to take a water route”, he says “We will leave in the cold, darkness of the night and take Mr. Hamilton's canoe and follow the north star that burns through the night and go up Chesapeake Bay to New York. This way, we look like fishermen and can avoid liability, I will also write protections for all of us.” The group agrees on the plans and will leave saturday night.