Vermont Overland BIKE

Distances and entry

• Overland (bike) – Men — $208.40
• Overland (bike) – Women — $208.40
• Overland (bike) – Nonbinary — $208.40
• Overland (bike) – Juniors — Free
• Overland (bike) – E Bikes — $240.31

About Vermont Overland BIKE

The Vermont Overland BIKE is a 50-mile (distances fluctuate based on years/course) dirt road bicycle race featuring close to 7,000 feet of climbing, eight sectors of Class-4 Roads (unmaintained ancient public through-ways), two sag stops, a magnificently scenic route and an awesome afterparty. 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.

This event is now 12+ years old and has a strong history of selling out registration in minutes to hours on opening day. If you're interested in acquiring a race entry for 2026, be sure to bookmark this page, set up your Movemint account, and set your alarms for 9 AM EST on January 1st!

RACE INFO:

• Saturday, August 15th, 2026

• Ascutney Outdoors, 449 Ski Tow Rd, Brownsville, VT 05037

• 50 Miles, 7,000' climbing

• 9 AM Start

• Race is limited to 1000 riders.

• Registration Opens on January 1st, 2026 at 9 AM EST.

• Compete in the OVERLAND TROPHY: An overall competition between our 15-mile Overland Trail running race and 55-mile Overland bicycle race. Read more here.

REGISTRATION:

• Registration opens at 9 am on January 1st, 2026, book this page 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 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). Please see Movemint for further information on how to make transfers. Read our full no refund and deferral policy here. 

• By registering for and participating in a Vermont Overland event, you are agreeing to our Privacy Policy.