Race Info
Saturday, August 24th, 2024
Ascutney Outdoors, Ski Tow Road, West Windsor, Vermont
55 Miles, 7,000' climbing
10 AM Start
Race is limited to 1000 riders.
Registration Opens on January 1st, 2024 at 9 AM.
Compete in the OVERLAND TROPHY
An overall competition between our 14-mile Overland Trail running race and 55-mile Overland bicycle race. Read more here.
About The Overland
The Overland is a 55-mile (distances fluctuate based on years/course) dirt road bicycle ride featuring close to 7,000 feet of climbing, eight sectors of Class4 Roads (unmaintained ancient public through-ways), two sag stops, a magnificently scenic route and an awesome party afterwards. It’s the ultimate overland adventure ride. Open dirt roads, amazing scenery and an epic course unlike any you’ve ever ridden before, all within a beautiful Vermont pastoral setting.
The purpose of this race is to promote the wonderful world of overland adventure riding and to benefit the Reading/West Windsor Food Shelf, Ascutney Outdoors and WAMBA–all integral organizations in the event’s host towns of Reading/West Windsor/Woodstock.
Registration
Registration opens at 9 am on January 1st, 2024. Bookmark the RunReg link and set your calendars!
Juniors race for FREE. Always.
West Windsor locals have a guaranteed spot. Contact us with your address.
We save space for women.
Registering for a Vermont Overland event is a commitment to yourself, our charities, the local West Windsor community, and our Vermont Overland Staff. We take this very seriously and have developed our registration and no-refund policies to around this fact.
Vermont Overland does not process or handle refunds and reserves the right to postpone, cancel or defer the event in any way shape, or form without issuing refunds whatsoever. However, as with all Vermont Overland events, if you can’t make it, you may privately assign your registration to whomever you like (this requires you to find a rider on your own and handle payment on your own) or send your spot to the next person in line on the waitlist (this only applies to categories that currently have people on a waitlist – there are no guarantees that our waitlists will be populated). If you decide to send your spot to the next person on the waitlist, BikeReg will process a 50% refund. Please see the BikeReg Knowledge Base for further information on how to make transfers.
By registering for and participating in a Vermont Overland event, you are agreeing to our Privacy Policy.
*** By registering for a Vermont Overland event, you’re agreeing to follow all local and state-mandated guidelines regarding safety and COVID-19. For more info, visit our FAQ page.
Volunteer
We COULD NOT pull off this event without our host of wonderful volunteers. There’s always a lot to do, from directing parking, helping at the registration table, helping with food, traffic flaggers, and many other tasks. Our volunteers are the heart and soul of the party! All Vermont Overland volunteers are treated to free meals from The Brownsville Butcher & Pantry as well as Vermont Overland swag. If you have an interest in volunteering, please sign up below! After you submit the form, the Vermont Overland team will reach out directly.
Volunteer Event dates: August 20-23rd (set up), 24th (race day), and 26th (clean up).
