One of the high points in metropolitan Boston-- literally and figuratively -- for local and visiting riders alike was Corey Hill in Brookline. Wheelmen strove to become the first to make it to the top of the hill and, after that barrier was broken in 1883, to set a new record time or simply challenge themselves to conquer the steep incline.
Bicycle manufacturers and sellers even promoted in advertisements the fact that their bicycles had made it to the top of Corey Hill.
"The hill is one of the steepest and longest in the vicinity of Boston," wrote the Boston Daily Globe on July 29, 1883, shortly after the first successful ascent "and hundreds of wheelmen have unsuccessfully tried to ride up."
The length of Corey Hill is 2300 feet [continued the Globe article], height 199 feet; average grade, one foot in 11.41. On the last 158 feet the average grade is one feet in 7.85 feet, and for the next 170 feet lower down the rise is one foot in every 7.87 feet
W.W. Stall, a Boston bicycle and tricycle dealer, was the first to make it to the top, in July 1883. He rode a Victor Tricycle like the one shown in the ad at left.
Later that month, H.D. Corey (fittingly enough) became the first to make the climb on a bicycle, a Rudge Light Roadster similar to the 1887 model pictured at left below. Corey was a noted Boston wheelman. (The following year he would become one of the first to ride a bicycle down Mt. Washington, the highest peak in New England.)
Annual Corey Hill climbs, organized by the Boston Bicycle Club, were held for the next several years. The 1886 event, part of the League of American Wheelman gathering in Boston, attracted particularly large crowds. (See the Harper's Weekly illustration at the top of this story and one from the Boston Globe below.)
Organized climbs were not the only way to attempt the hill, of course. The 1886 Cyclists' Road Book of Boston and Vicinity included Corey Hill as part of Route Five, starting at Trinity Church in the Back Bay. "The view from the top of the hill well repays for the labor of ascending it, on foot if necessary," said the guide, noting that the final, steepest 158 feet "is what generally bowls over the cyclist."