Tom Rowland was born in Ware around 1660. Nothing is known of his parents, apart from the fact that at some point they sent Rowland to act as an apprentice to a bricklayer. This career would have given Rowland some stability in life, but Rowland was reputedly of “a slothful and idle disposition”. Whilst acting as an apprentice he seems to have fallen into bad company and before long he stole a horse belonging to the Duke of Beaufort in Badminton, Gloucestershire. This was an extremely risky crime, as horse theft could be punished with death.
Knowing the danger of the crime he had committed, and being aware he could not return to normal life, Tom Rowland became a highwayman from that day onwards. He was a highwayman for 18 years, an incredibly long career. Contemporary reports revealed how Rowland managed to go for so long without being caught: “he always robbed in women’s apparel, which disguise was the means of his reigning so long in his villainy”. The Newgate Calendar notes that whilst he would act like a lady by riding side-saddle, he would ride astride if he needed to make a quick getaway.
Rowland’s reign as a highway robber came to an end in 1699 when he tried to rob a person on Hounslow Heath who was carrying a significant £1,200 worth of valuable bone-lace. He was caught and found guilty and was sentenced to death.
However, Rowland lived his life to the full even at the end. Due to the wealth he had accumulated during his time as a highwayman, he was able to pay for luxurious prison lodgings. The Newgate Calendar also notes with disgust that on the morning of his execution he paid for a “common woman” to visit him and he “had the unparalleled audaciousness to act carnally with her”. Rowland was executed on Friday 24th October 1699, aged forty.
To his contemporaries, Rowland dressing as a woman was solely a way to evade capture and detection whilst living outside of the law. This may well be true: disguises were often a way for highway robbers to extend their success, with cross-dressing by both women and men. However, author John Higgs in his book “From Watling Street: Travels Through Britain and Its Ever-Present Past” raises the possibility that Tom Rowland may have identified as a woman and lived as a highway robber as a way to be their authentic self.
Rowland dressed as a woman for eighteen years, so it is possible that this may have been part of his identity. Although dressing as a woman could help his disguise, women’s clothes in the 17th century were not typically well suited to riding.
Rowland does appear to have had sex with a woman on the morning of his execution, and as the only real records we have of Rowland’s life is from the Newgate Calendar which briefly describes his life and crimes, we have no way of knowing how Rowland himself identified. Rowland could have been a transwoman who was a lesbian, they could have been a heterosexual, cis man and enjoyed wearing women’s clothes, they could have been bisexual and used cross-dressing as a way to explore this, or they could simply have been cross-dressing as a disguise. Without Rowland’s own words, we cannot tell.