Strambecco rates the best gravel cycling events New England 2025 based on various factors, including reputation, route quality, location, rider feedback, and the overall uniqueness of the event or race. Spanning upstate New York, Connecticut, Massachusetts, New Hampshire, Vermont, Maine, and Rhode Island — New England terrain features of Strambecco’s best list are typically hard-packed dirt & stone with the occasional rocky, rooty sections. You’ll also find many rollers with short, steep climbs, including some hike-a-bike. Of course, whether can change course conditions dramatically, especially for those Spring events where you likely throw puddles and mud.
If we had to rate the best of the best gravel cycling events New England 2025, we start with Rasputista and Tour of the Battenkill, two great early-season options. Battenkill bills itself the “Queen of the Spring Classics” and is one of the oldest gravel events in the country. Battenkill is produced by Ventures Endurance, who are producers of the famed multi-day RAGBRAI (Ride Across Iowa) and Ride the Rockies. The Vermont Overland is an extremely popular event in late August.
Strambecco does not list every event. We strive to identify and review events that are special and noteworthy. If you have suggestions on other events we should consider or review, please get in touch with us here or send us a note at editors@strambecco.com.
With start-finish at the Stratton Mountain Resort, the VT Monster Gravel Grinder 2026 offers three-course options spanning 100 miles, 78, and 48 miles. However, the 78-mile course comes with 70% gravel and…
For gravel cycling enthusiasts, the Deerfield Dirt Road Randonnée (D2R2) 2026 stands as a beacon of adventure, camaraderie, and breathtaking scenery. Held annually in western Massachusetts, D2R2 has become a mecca for…
The Vermont Overland Bike 2026 is one of the most popular and longest-running gravel cycling events in the US. The scenic route spans 55 miles and features 7,000 feet of climbing, seven…
This gravel classic returns to its roots for its 10th anniversary, reintroducing the notorious Cyberia section that built its reputation. The course features deep mud, steep grades, and Vermont’s unpredictable early spring…
Last updated June 7, 2026 Event for 2027 has not been confirmed yet… Billed as the “Queen of the Classics,” the Tour of the Battenkill 2027 is a legendary 75-mile mixed surface…




