New Englanders looking for a tough-bones road cycling event with a spirit of camaraderie and a great party at the finish can look no further than the famed B2VT (Boston to Vermont) 2026 road cycling event in June each year.

In the early 2000s, Harpoon Brewery opened a second brewery in Windsor, Vermont. A group of elite cyclists from Team Psycho seized this opportunity to embark on the inaugural B2B ride, setting the wheels in motion for what would become the B2VT (Boston to Vermont) 2026 ride. With nothing but a SAG wagon stocked with essentials like water, tires, tubes, and tools, they took on the challenging route. Upon reaching Windsor, a keg (or maybe more) was rolled out from the brewery for a joyous post-ride celebration.

The B2VT event has grown, both in terms of participants and the intensity of the challenge. In 2014, the B2B became the B2VT, and a tougher course was unveiled, pushing riders to their limits. However, what has remained constant is the spirit of the event—a tough, bare-bones ride with the ultimate rewards of camaraderie and a memorable party at the finish. Strambecco rates B2VT as one of the Best Road Cycling events in New England. The event is produced by Streamline Events who also produced the highly acclaimed VT Monster Gravel Grinder.

B2VT Ride is designed to accommodate a wide range of cyclists. The event offers three distances, ensuring that every participant can find a ride that suits their skills and fitness level. The signature event is a whopping 142 miles with 9,000+ feet of elevation gain.

For those seeking an iron-distance challenge, the 103-mile route starts from Ashby, Massachusetts, and includes 8,000 feet of climbing, with four significant climbs that test even the most experienced cyclists. From “The Primer” to “The Burner,” each ascent offers a dose of reality, with the grand finale known as “Big Bear” delivering the ultimate high point of the course.

The 62-mile metric century ride offers an equally challenging yet slightly shorter option. Starting from Chesterfield, riders will conquer 5,000 feet of climbing, including the grueling “Burner” and the exhilarating “Big Bear” climb, making this a tough 62 miles of relentless ups and downs.

The B2VT Ride places great importance on safety and respect for the communities it passes through. Riders are expected to follow all traffic laws and be respectful to other road users. The event emphasizes safe and considerate riding, with riders encouraged to stay in double file or single file on narrow roads.

While the event offers support through world-class neutral road support and stocked water stops, participants are expected to ride unassisted and finish under their own power. Riders are encouraged to be self-reliant, with each cyclist responsible for servicing their own bikes, including repairing flats and conducting minor repairs.

The B2VT Ride culminates in a memorable post-ride celebration at Stratton Mountain Resort in Vermont. Partnerships with Stratton provide participants, as well as their friends and families, with special lodging discounts. The event operator offers return bus options to transport riders, bikes, and gear back to the starting line in Bedford, MA.