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Backstory: Retracing Annie Londonderry's Victorian odyssey

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For me, riding at least a couple of hundred miles in Annie's shoes, from Boston to New York earlier this month, was the culmination of three years of research into her long-forgotten story. It was the next logical step in my own odyssey on the Londonderry trail that began with a query from a perfect stranger looking for information about her and making it clear that Annie was my great-grandfather's sister – even though no one in my family had ever heard of her.

August 12 brought clear blue skies in Boston, a perfect day for cycling. After a brief ceremony at the Massachusetts State House, at the precise spot where Annie's journey began 112 years ago, a couple dozen cyclists and I, some on high-wheel bikes from the 1880s, pushed off and, like Annie, flew away like kites down Beacon Street.

It is presumptuous to think that riding a lightweight carbon-fiber bike, powered by Gatorade and energy bars, and with a cellphone for emergencies, is much like Annie's experience in 1894. Annie began her journey on a 42-pound Columbia bike that weighed twice as much as mine. It had but a single gear and no freewheeling mechanism, which meant that the pedals spin with the wheels. Going downhill she placed her feet on rests mounted on the front fork, lest the spinning pedals tangle in her skirts and bring her crashing to the ground. (Later in her trip Annie acquired a man's Sterling bicycle, donned bloomers, and then a man's riding suit. The Sterling, unlike the Columbia, had no brake.) Annie traveled roads that ranged from smooth macadam in the cities to impassable sand that required her to push her bike.

On the flip side, Annie rode without the noise and constant danger of the fast-moving traffic we contended with much of the way, though we rode secondary roads and rural byways whenever possible. "Road books" for cyclists offering meticulously detailed routes between cities as distant as New York and Chicago were available in the 1890s. Today, it would be possible to navigate using a portable GPS system, though we relied on bike maps which were sometimes unreliable.

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