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 sectors of “Vermont pavé” (unmaintained ancient public roads), and two well-fortified sag stops. It’s the ultimate overland adventure ride and one that at Strambecco, we consider to be one of the Best Gravel Events in New England. Open dirt roads, amazing scenery, and an epic course unlike any you’ve ever ridden before, all within a beautiful Vermont pastoral setting. Don’t be fooled by the rolling nature of Vermont’s Green Mountain roads; the route comes with a barrage of short, punchy climbs.

The event is produced by Vermont Overland, an organization dedicated to promoting a variety of gravel, adventure cycling, and running events every year. The Vermont Overland Bike 2026 specifically benefits the Reading/West Windsor Food Shelf, Ascutney Outdoors, and WAMBA all integral organizations in the event’s host town of Reading/West Windsor.

With a field limit of 1,000 participants, this is one of the most popular gravel events in the country. This event sells out within hours – registration opens annually on Jan 1, so it’s important to mark your calendar.

The Overland Bike kicks off at 10 AM on Saturday with a mass start. The challenging terrain and seven Class-4 unmaintained road sectors demand technical skills, preparation, and determination. These sectors vary from leisurely stretches to demanding ascents, ensuring an adventure that tests every aspect of your gravel cycling abilities.

The event emphasizes self-sufficiency while providing necessary support for a successful journey. Two aid stations powered by Untapped Maple are strategically placed along the route. However, it’s recommended that participants start the ride with all the essentials for self-sufficiency. The event is self-navigated, enhancing the authenticity of the overland adventure. Riders are required to have the route pre-loaded on their GPS devices or carry printed cue sheets.

The route is predominantly composed of dirt roads, making gravel-specific bikes or cross bikes with a minimum of 32c tires and low gearing ideal choices. A hardtail mountain bike is also a suitable option, especially for those new to dirt road riding. While road bikes are allowed, they might not provide the optimal experience on this demanding terrain.

Once you cross the finish line, the festivities continue with a post-ride party and cookout presented by The Brownsville Butcher & Pantry. Live music, a vibrant expo featuring partners like Specialized Bicycles and SRAM, create an atmosphere of camaraderie and celebration. The top three overall, women, non-binary, and men, are celebrated in a podium ceremony near the finish line.

Vermont Overland also produces the Overland’s sister trail running event, the Vermont Overland Trail each spring. New in 2023 is the Overland TROPHY which is eligible to athletes that compete in both the running and cycling events. The top 3 participants win bragging rights to being the most well-rounded athletes with the ability to traverse a landscape efficiently no matter the mode, in addition to some cool custom Vermont Overland prizes.