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Best Cycling Events Massachusetts 2024

Best Cycling Events Massachusetts 2024

Pack of riders in B2VT Event

The team at Strambecco rates the Best Cycling Events Massachusetts 2024 based on various factors, including reputation, route quality, location, rider feedback, and the event’s or race’s overall uniqueness. Strambecco does not list every event.  We strive to identify and review special and noteworthy events, spanning Road, Gravel, and Mountain Bike events and races.

Massachusetts, with its diverse landscapes and rich cycling culture, is a haven for riders of all levels. Whether you’re a road cycling enthusiast or a mountain biking maven, the Bay State has something for everyone. Here, we’ll explore three of the best cycling events that make Massachusetts a cycling paradise.  If we had to pick the best of the Best Cycling Events Massachusetts 2024, we start with these three:

1. B2VT Ride: Border to Vermont Gravel Adventure

Event Overview: The B2VT Ride is the ultimate test of endurance and adventure for cyclists. Starting at the border of Massachusetts and finishing in Vermont, this epic gravel event stretches for 148 miles through the scenic New England countryside. Cyclists take on the challenge of rolling hills, dirt roads, and breathtaking landscapes.

Rider Experience: The B2VT Ride is not just about the destination; it’s about the journey. Riders tackle a mix of pavement and gravel, with challenging climbs that lead to awe-inspiring descents. The camaraderie among cyclists and the picturesque views along the route make this event a cherished experience for riders of all levels.


  • A unique opportunity to ride across state borders.
  • Satisfying post-ride festivities with food, drinks, and music.
  • Varied terrains for a well-rounded challenge.

2. Deerfield Dirt Road Randonnée: Gravel Cycling at Its Best

Event Overview: The Deerfield Dirt Road Randonnée (D2R2) is a gravel grinder’s dream come true. This event, hosted in the picturesque Pioneer Valley, offers multiple route options, catering to both novice and experienced cyclists. With loops ranging from 20 to 180 miles, riders can tailor their D2R2 experience to their level of expertise.

Rider Experience: D2R2 is known for its breathtaking scenery, challenging terrain, and exceptional support for riders. Gravel enthusiasts revel in the variety of surfaces, from pristine backcountry roads to rugged tracks, while taking in the serene landscapes that Massachusetts has to offer.


  • Multiple route options for all skill levels.
  • Stunning views of the Pioneer Valley and classic New England farmlands.
  • Well-organized and fully supported event with rest stops and SAG support.

3. Freetown 50 MTB Event: A Mountain Biker’s Paradise

Event Overview: If you’re a mountain biking aficionado, the Freetown 50 MTB Event is a must-attend. Located in the Freetown-Fall River State Forest, this event offers a unique blend of challenging singletrack trails, technical descents, and heart-pounding climbs. The 50-mile course promises an unforgettable adventure for riders seeking the thrill of off-road cycling.

Rider Experience: The Freetown 50 is renowned for its rugged trails and natural beauty. Riders navigate through dense forests, over rocky terrain, and across pristine water crossings. It’s a true test of skill and endurance, but the exhilaration of conquering nature’s obstacles is the ultimate reward.


  • Remote and unspoiled forested routes.
  • Technical challenges that keep even the most experienced riders engaged.
  • A celebration of mountain biking culture with fellow enthusiasts.

Massachusetts offers cyclists a diverse array of events, from the road-based B2VT Ride to the gravel grind of the Deerfield Dirt Road Randonnée, and the off-road adventure of the Freetown 50 MTB Event. Each of these events not only tests your mettle as a rider but also provides a unique opportunity to explore the state’s stunning landscapes and connect with fellow cyclists. So, gear up, saddle up, and experience the pedal paradise that Massachusetts has to offer.

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  Strambecco also rates the best Road, Gravel, and MTB events in greater New England.

B2VT finish at Stratton Mountain Resort

B2VT (Boston to Vermont)

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The Deerfield Dirt Road Randonnée (D2R2)

For gravel cycling enthusiasts, the Deerfield Dirt Road Randonnée (D2R2) stands as a beacon of adventure, camaraderie, and breathtaking scenery. Held annually in western Massachusetts, D2R2 has become a mecca for cyclists…
mountain biker and scenery at freetown 50 event

Freetown 50

Called the toughest mountain bike event in the Northeast, the Freetown 50 has made a name for itself as a challenging and extremely well-attended endurance mountain bike race in Assonet, Massachusetts. Initiated…
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