Pushing Through the Rain: Hundreds Ride George St. to Train Like the 'Worcester Whirlwind'

A Rainy Day Celebration of Cycling and Legacy

Despite the rain and chilly temperatures on Sunday, July 27, hundreds of people gathered at the base of George Street in Worcester to take part in the annual George Street Bike Challenge. This event is held in honor of Marshall "Major" Taylor, a legendary cyclist who was once known as "the Worcester Whirlwind." Taylor, originally from Indianapolis, spent 25 years living in Worcester, where he trained by biking up George Street—a steep road that connects Main and Harvard streets.

Now nearly 100 years after Taylor's passing in 1932, cyclists continue to gather each year to challenge themselves on the same route that once tested the endurance of one of the greatest athletes of his time. The race has become a cherished tradition, drawing participants from across the region.

Mary Porter, a volunteer with the Seven Hills Wheelman group that organizes the event, noted that this year saw the largest turnout yet. Over 100 people took part, with about 70 registering online beforehand and another 30 showing up on the day of the event. Porter believed those who arrived on race day were particularly dedicated, as they braved the rain to take part.

Many of the participants were clearly experienced cyclists, dressed in cycling shorts, shoes, and jerseys featuring Major Taylor’s image. Others came in more casual attire, wearing T-shirts and sneakers, ready to tackle the 18% incline hill that stretches for 500 feet.

Jeff Greenwood of Leicester was among the competitors this year. He had watched the race for the first time last year and was inspired to join this year. His wife, Katelyn, described the rain as "torrential" when they arrived with their three children to cheer him on. Despite the weather, they stayed, holding signs and waiting for Jeff to complete the climb.

The Greenwoods weren’t the only family to make the event a special occasion. Cas Roberts of Worcester, who has competed in the race four or five times, brought his son, William, for his first experience. Roberts joked that he expected to go slower than ever before, but he and his son had practiced the climb a few days earlier to prepare.

Nathan Wong of Worcester also brought his sons to the event. His youngest son, August, joined him on the climb, while his 14-year-old twins, Lathe and Ulysses, raced separately for the first time. Four years ago, Wong had taken all three kids with him, with one riding on the handlebars and the others on a seat attached to his bike. This year, the twins were racing on their own, marking a new milestone for the family.

In addition to the cyclists, members of the Major Taylor Association were present at the event. Melanie Morris of Boston, who has been on the board for about five years, was selling raffle tickets and wearing a vintage cycling cap with "1899" embroidered on the brim—the year Taylor became a world champion. She expressed her admiration for Taylor’s story, noting that he broke barriers in the sports world.

Morris is also involved in an upcoming movie about Taylor, which she hopes will bring more attention to his legacy. Meanwhile, Cyrille Vincent of Worcester, who is producing a documentary about Taylor using period costumes and actors, was also at the event. He wore a similar cycling cap to Morris and shared that he has raised about 5% of the $1.25 million needed for the film. Fundraising events are planned for August 28 and October 11.

The George Street Bike Challenge began in 2002 and has been held almost every year since. This year, the event included a vendors' row and a raffle for a new bicycle, adding to the community spirit and celebration of Major Taylor’s enduring legacy.