This legendary New England road ride traces its roots to the early 2000s when Team Psycho cyclists rode from Boston to Harpoon Brewery’s new Windsor, Vermont location with nothing but a SAG wagon and the promise of kegs at the finish. What started as an adventurous brewery run has evolved into one of the region’s most respected endurance challenges, transforming in 2014 from the original B2B into the more demanding B2VT with extended distance and serious elevation.

The signature 142-mile route delivers over 9,000 feet of climbing through New England’s rolling terrain. For those seeking something slightly more manageable, the 103-mile option starts from Ashby, Massachusetts and includes 8,000 feet of climbing across four major ascents nicknamed “The Primer,” “The Burner,” and culminating with “Big Bear.” The 62-mile metric century from Chesterfield still packs 5,000 feet of elevation gain, proving that even the shortest option maintains the event’s no-compromise reputation.

This is decidedly a bare-bones affair that emphasizes self-reliance. Riders handle their own mechanicals and navigate open roads alongside vehicle traffic, supported by neutral road support and strategically placed water stops. The ethos remains firmly rooted in personal responsibility and respect for local communities.

The reward for grinding through New England’s challenging terrain comes at Stratton Mountain Resort, where the post-ride celebration maintains the original spirit of that first Harpoon keg rollout. A return bus service handles the logistics of getting riders and bikes back to the Bedford, Massachusetts starting point, completing a weekend that balances serious athletic challenge with genuine cycling community.