Conquer challenging New England terrain on this classic 100k adventure.

The Hopkinton the Boot 100k, part of the New England Randonneurs Series, is a 100 km (62-mile) unsupported endurance cycling event. Starting in Boston’s Jamaica Plain neighborhood, this brevet challenges riders to embrace the spirit of randonneuring—self-reliance and navigation—while traversing the historic suburbs and rolling landscapes of Massachusetts. Cyclists must complete the distance within set time limits, strategize at checkpoints, and experience New England’s scenic charm on a hilly and memorable course.

A loop route beginning in Jamaica Plain, Boston, featuring mixed paved suburban and rural roads, with frequent rolling climbs and a checkpoint-based navigation challenge typical of randonneuring events.

• Ride through historic Boston suburbs and picturesque rural Massachusetts
• Strategic checkpoint navigation and self-supported cycling
• Qualifier for major international endurance events like Paris-Brest-Paris