On the Big Rock Candy Mountain /All the cops have wooden legs/ The bulldogs all have rubber teeth/ And the hens lay soft boiled eggs…
The original hobo’s version of this children’s song contrasts sharply with the reality of being a tramp in Hartford throughout the late 19th and early 20th centuries. Examples of the hobo’s life could be found in the North Meadows at the edge of Hartford’s railroad yard.
Originally, most tramps had been tradesmen or artisans: weavers, shoemakers, machinists, masons. They were workers who could not find jobs in the financial crash of the 1870s and their numbers increased as one economic slump followed another right up until the great depression of the 1930s. Louise Newkirk, for many years a cook in a local Hartford day care center, remembers a tar paper shack hobo jungle populated by men and sometimes women who had been discarded by–or who had rejected– proper society.
Many hoboes rode the rails, building a culture of language and ethics that still exists today. Hopping the freights with the unemployed were the Wobblies–labor organizers for the Industrial Workers of the World (IWW), the “One Big Union” that rocked the textile industry in Lawrence Massachusetts, organized workers in Hartford, and spread the union cause throughout the country. Hoboes and Wobblies had a common antagonist in the form of the Pinkerton Agency, a private police army that specialized in busting unions and breaking heads in factories and railroad yards. Allen Pinkerton’s account of his exploits was set down in his book “Strikers, Communists, Tramps and Detectives.”
Even though”vagabonds, tramps and thieves” were banned from entering Hartford as far back as 1678, not every attitude toward hoboes was unsympathetic. In the early 20th century, Hartford’s Socialist Labor Party campaigned to eliminate “tramp laws” used to jail the homeless. Hartford residents in the 1890s read tales like “John Smith, Tramp,” a short story about a mysterious stranger who approaches a widow for help. “Are you brute or human?” she demands as she points a gun at him. The woman eventually allows the ragged man to work for room and board but he soon quietly disappears. A few months later, he sends the widow a check for her kindness. She discovers he is a judge who took to the roads after mistakenly believing he had killed his wife.

The study of hoboes was often relegated to such romantic folklore. But Trinity College professor and clergyman John James McCook made it his business to study the lives of displaced people from 1890 until his death in 1927. McCook surveyed, photographed, and corresponded with men such as Pittsburgh Phil and Connecticut Fatty to get to the root of the “tramp problem,” which he initially ascribed to personal defects. He focused on the use of hoboes by local politicians for what was called “venal voting” or vote buying. He even set up a citizens’ committee, which he said included Pinkerton agents, to monitor polling places. McCook also proposed government control and distribution of liquor and the establishment of a reformatory where vagrants would work for their room and board. Attempting to have the state institution built on Fairfield Avenue, McCook seriously misjudged the political opposition of wealthy neighbors and the plan was abandoned after years of work.
It was Roving Bill Aspinwall who tried to show Dr. McCook that the reverend’s answers were superficial. Bill and McCook corresponded for almost twenty-five years; Aspinwall wrote to McCook on the road anywhere from Niagara Falls to Mexico. He had been a worker at a Rhode Island woolen mill. Like many others, he was a victim of capitalism’s boom-and-bust cycle. Aspinwall was frank about his drinking problem, but unlike McCook, he considered it more the result of his inability to stay employed, not the other way around. His travels allowed him to become a barometer of the country’s financial condition; the more tramps he met on the road, the more he recognized that another depression was coming.
Roving Bill believed that if Dr. McCook wanted to rid Hartford of vice and alcohol abuse, the solution was full employment. As he wrote to McCook, society had to “abolish industrial booms, financial crises, business slumps, hard times!”
Hobo life rose with the railroads and the chaos created by the race for profits. Hartford’s hobo neighborhood was bulldozed to make way for Route 91. Nowadays homeless shelters have largely replaced fleabag hotels and hobo jungles in the city. But when hard times hit, the unemployed and homeless seek out a more independent way to live. Today you will still find individuals or small tribes of homeless men and women spending their summers in an abandoned trailer truck near the north Hartford railroad tracks, or under the giant highway bridges.