The Overland

The Overland is a premier 55-mile dirt road bicycle race set against the stunning backdrop of Ascutney Outdoors in West Windsor, Vermont. With approximately 7,000 feet of climbing, participants will navigate a challenging course that includes eight sectors of Class 4 roads, offering a unique blend of adventure and scenic beauty. The race features two sag stops to support riders along the way, culminating in a celebratory gathering that highlights the spirit of community and outdoor exploration. This event not only showcases the thrill of overland adventure riding but also serves a greater purpose by benefiting local organizations, including the Reading/West Windsor Food Shelf and Ascutney Outdoors. The Overland encourages participation from all, with juniors racing for free and guaranteed spots for West Windsor locals. The commitment to fostering a welcoming environment for women is also a key aspect of the race, ensuring inclusivity and support for all riders. Registration opens at the beginning of the year, and participants are encouraged to secure their spots early, as the race is limited to 1,000 riders. Volunteers play a vital role in the success of the event, contributing to various tasks that enhance the overall experience. With a focus on safety and community engagement, The Overland promises an unforgettable adventure for cyclists and supporters alike.