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The Overland

August 26, 2024

gravel cyclists at starting line at the overland event

The Overland 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 for 2023. 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 — all to share the spirit of adventure and make it possible for people to explore Vermont on their own.  The Overland 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, let alone New England. This event sells out within hours – registration opens annually on Jan 1, so it’s important to mark your calendar.

Event & Course Info

The Overland kicks off at 10AM on Saturday with a mass start. The event offers one route option (55 miles / 7,000 ft of elevation gain), carefully designed to provide participants with a journey that’s equal parts demanding and rewarding. 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 Overland emphasizes self-sufficiency while providing the necessary support for a successful journey, organizers believe that self and group navigation is part of the spirit of gravel cycling. 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 aid stations are there to supplement your hydration and fuel needs. 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. This navigation approach adds an element of exploration and self-reliance to the experience.

The Overland blurs the lines between cycling disciplines, making bike selection an important aspect. 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. Visit Woodstock Sports for any bike needs while you are in town for the event.

Once you cross the finish line, the festivities continue after the race with a post-ride party and cookout presented by The Brownsville Butcher & Pantry. Live music, a vibrant expo featuring partners like Specialized Bicycles, SRAM, and more, 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. This recognition adds a competitive edge to the event while honoring the diverse participants who take on the challenge.

Area Accommodations and Things to Do

Get the full Overland experience by planning to camp at and around Ascutney Outdoors by adding this to your registration. There are options to pitch a tent, camp in your car, or camp in your 4×4. If you prefer more traditional lodging accommodations, check out Kedron Valley Inn or the Woodstock Inn or the full list of recommended hotels. There are also vacation rentals to choose from, from this stylish guesthouse to this peaceful retreat perfect for a group participating in The Overland.

Nestled in the charming embrace of Vermont’s natural beauty, West Windsor offers not only breathtaking landscapes but also a delightful culinary scene that celebrates organic and locally sourced foods. As you explore the town’s quaint streets, you’ll discover a range of dining options like South Woodstock Country Store and Mon Vert Cafe, that reflect the region’s commitment to sustainability, organic ingredients, and a farm-to-table ethos.

For outdoor athletes and adventure enthusiasts, West Windsor, Vermont, is a haven of possibilities during the summer months. From heart-pounding activities to serene nature explorations, the town and its surroundings offer a diverse range of options that cater to every adrenaline level. Pack your mountain bike to enjoy the Ascutney Trails after the event has concluded. This mountain biking haven offers an extensive network of trails that cater to various skill levels, from beginners to seasoned riders. The diverse terrain includes thrilling descents, technical challenges, and flowy singletrack.

Hiking the Weathersfield Trail to the summit of Mount Ascutney is an ideal choice for those looking for a challenging hike that rewards your efforts with panoramic views that stretch across Vermont and beyond. As you ascend through lush forests and rocky terrain, you’ll experience a true connection with nature. The summit’s observation tower provides a vantage point to admire the surrounding landscapes.

For those who find solace in the water, kayaking or canoeing on the Connecticut River offers a serene and invigorating escape. Launch your vessel from West Windsor’s riverside areas and embark on a journey along the tranquil waters. You can also swim in secret swimming holes like the freshwater Kedron Pond, this 20ft swimming hole, and Brook Road swimming hole

Related Events

Vermont Overland also produces the Overland’s sister trail running event, the Vermont Overland Trail each spring which is one of the Best Trail Running Events in New England. 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.

Vermont’s topography and outdoor culture make it a perfect host for other premiere endurance events throughout the year including top gravel cycling events such as Rasputista and VT Monster produced by Streamline Events. For the multi discipline cyclists, the state is also host to the Vermont 50 MTB organized by Ascutney Outdoors / Vermont Adaptive Ski & Sports and the epic Fox US Open of Mountain Biking, both of which are considered to be some of the Best Mountain Bike Events in New England. The Vermont Gran Fondo road cycling event, one of the Best Road Cycling Events in New England, is a stop on the Gran Fondo World Tour and a Gran Fondo National Series event. Finally, the trail runners of the group have a few great options for top tier events including the Vermont 50 Ultra Run which takes place the same day as its MTB partner event, as well as the Vermont 100 Endurance Race a Grand Slam of Ultrarunning event.


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Vermont Overland


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