Sunday, July 27, 2025 | 6:30 AM Start | Winchester to Worcester and back
Get ready for one of CRW's most inspiring rides of the year! The Major Taylor Century combines challenging miles with powerful cycling history, featuring a midpoint stop for the legendary George Street Bike Challenge, the same steep hill where world champion Major Taylor once trained.
REGISTER FOR THE CENTURY
A Champion's Story
Marshall Walter "Major" Taylor was a trailblazer who shattered barriers on and off the cycling track. Born in Indianapolis in 1878, Taylor moved to Worcester as a teenager, drawn to the city's thriving bicycle industry. Training on George Street's punishing grades helped forge him into the 1899 world sprint cycling champion—the first African American to achieve world champion status in any sport. Despite facing severe racial discrimination, Taylor's grace and determination earned him the nickname "The Worcester Whirlwind."
The Challenge Awaits
Our 105-mile out-and-back journey departs from Winchester and features a special midpoint stop in Worcester at the annual George Street Bike Challenge. This 500-foot, 18% average grade monster has humbled cyclists since Taylor's era. The current record stands at just 22.19 seconds.
Key Details:
- Start: 6:30 AM sharp from Shannon Beach, Winchester
- Pace: Steady 15-17 mph (GPS required, no cue sheets)
- George Street arrival: 9:30 AM for photos at the Major Taylor statue
- Hill climb window: 9:45-10:30 AM (separate $20 entry)
- Finish: ~2:15 PM back in Winchester
REGISTER FOR GEORGE STREET CHALLENGE
Ready to Roll?
This fast-paced century demands preparation and commitment. Pack your repair kit, have the route on your GPS, and be ready to maintain our ambitious schedule. Whether you watch from the sidelines or test your legs against George Street's intimidating grade, you'll be part of an event honoring Major Taylor's memory.
Contact ride leader Randolph Williams with questions, and if you're entering the George Street Challenge, let him know so we can cheer you on!
