On February 22, 1861, the trek almost failed before it even began. A large crowd had gathered at the Boston State House in anticipation of Weston’s departure. But as he stepped out of his carriage to greet the onlookers, he was stopped by a debt collector looking to settle up on a debt Weston owed – one thing about Weston is that he was frequently in debt. When Weston made it clear that he would not be able to settle his debt until he returned from Washington, the officer informed him that he would be placed under arrest. As this was occurring, another debt collector stepped up and presented a different claim against Weston. After an hour of intense negotiation, the would-be walker was released on the condition that he pay his debts upon his return to Boston.
At a quarter to one, Weston made his way back to the State House, where he gave a brief speech at the insistence of the crowd, while explaining that he “preferred to keep his breath for the long journey.” Weston shared that he felt a certain calling to complete this walk: “Abraham Lincoln had been elected by the people, President of these United States, and he believed he had been elected to walk to Washington to see him inaugurated, and with God’s help he would do it.” Following his speech, Weston and his companions set off, with a crowd of several hundred following them down Beacon Street. He traveled the first five miles out from Boston in 47 minutes and reached his first stop in Framingham 15 minutes earlier than he had originally intended, despite his delayed departure. In Framingham, Weston and his crew were entertained at the Framingham Hotel, where he encountered a number of ladies who “desired to send a kiss to the President.” Mr. Weston gladly accepted these kisses from the ladies, but he told them he could not promise to deliver them to the president.
As Weston continued on his journey, he encountered snow and ice in his path and at one point was chased by a dog, which led to an ankle sprain. He walked on rough and muddy roads, even while injured and in pain. In Worcester, Massachusetts, Weston encountered yet another debt collector. Despite these obstacles, Weston stated that he would “sooner die on the road than back down.”