Our Story
Vermont Overland began in 2009 with a simple idea: share the wild, rugged beauty of Vermont’s ancient roads and legal through-ways with people who crave adventure. What started as a quirky experiment—part classic overlanding, part old-school bike racing—quickly grew into something bigger. The Overland BIKE became a ride unlike any other. Playful, demanding, wildly fun… a challenge that captured the imaginations and training calendars of cyclists far beyond Vermont.
Today, Vermont Overland is one of the most unique and recognized names in gravel riding and adventure travel. Our flagship event, The Overland BIKE, remains at the heart of what we do, now joined by The Overland RUN, and experiences that celebrate the same spirit: connecting people to Vermont, to community, and to adventure.
Our mission is to promote adventure travel. We want it to be more accessible to all, authentic, and deeply connected to place. Through world-class gravel cycling and trail running events, curated digital routes & guide books, free video courses, products, gear and the occasional documentary film. Why do we do these things? Because those who seek adventure by traversing a landscape and more likely to care for and protect that landscape.
So what does Vermont Overland actually mean? The simplest answer is opaque and paradoxical: many things by fewer ways.
