She was a cunning Underground Railroad ‘conductor’
For more than a decade, Tubman crossed back and forth into the Eastern Shore of Maryland to rescue slaves and guide them to freedom. It was dangerous, highly-risky work. The fact that Tubman managed to work undetected and maintain her freedom for so long is testament to her cunning. She knew the risks and so planned every trip meticulously. While she would improvise if necessary, for the most part, she liked to follow her own rules and demanded others obey her instructions to the letter.
Above all, she had a rule of working during winter months. Not only did this time of year offer more chance to hide and travel under the cover of darkness, it also meant that fewer people were out on the streets. What’s more, Tubman would look less conspicuous wrapped up in bundles of clothes, plus nobody would think twice about people being hidden away in their houses rather than out and about. As one contemporary of Tubman famously recalled of her methods: “She always came in the winter, when the nights are long and dark, and people who have homes stay in them.”
Tubman could do nothing to disguise the fact she was a short woman of color. But she did do her best to disguise herself. She would recycle a collection of bonnets and outfits. Additionally, she would always try and look busy: when she and some slaves were hiding out at a home on the Underground Railroad, for example, she might sweep the steps to make it look like she was a domestic servant. On other occasions, she would walk with live chickens under her arms. This way, white people would usually just ignore her, believing her to be a slave or servant running errands.