Register for the Vermont Overland BIKE (event date: August 15th, 2026)
Register for the Vermont Overland RUN (event date: August 16th, 2026)
Register for both and compete in the Vermont Overland TROPHY (event dates: August 15-16th, 2026)
Vermont Overland was founded in the belief that all-surface exploration is transformative.
Today we still host our flagship event, The Overland (bike) & The Overland (run), along with many other smaller events with the goal of sharing the spirit of adventure while also supporting the local communities of Vermont that make these events possible.
Be sure to follow us on YouTube, Instagram, Facebook and Strava to join the party. Also, subscribe to our email list below for updates and info as our events tend to sell out within minutes.
Moments, memories & more from our 2025 edition of the Vermont Overland BIKE. These images remind us why we put on this event year after year.
Photos by – Tom Dils & Ansel Dickey
Moments, memories & more from our 2025 edition of The Overland RUN – our biggest running event to date. We’re proud of where we started and excited to continue watching this one of a kind all-surface running race grow.
Words are never enough. Photos are better, but still not enough to describe everything that was Vermont Overland 2025. The only thing we can accurately express is a heartfelt THANK YOU.
Overland is an invitation to go beyond what’s charted, to explore Vermont’s hidden public corridors, appreciate all this beautiful state has to offer and to rediscover what adventure really feels like.
If you're not already registered, join us 🤘
In the build up to registration day on 1/1/2025 we thought it might be fun to talk about how we stay motivated during these cold winter months! While we’re dreaming of spring trails, and summer gravel, we keep the engines lubricated in a variety of ways. Spoiler: It’s not all about the bike.
Registration day is 1/1/2025 at 9 AM! We’re moving away from BikeReg and switching our registration platform to movemint.cc, and we couldn’t be more stoked.
We created this art work for fun… we’re trying to poll our audience to see if there’s enough interest in turning it into something physical and tactile like a poster, shirt, patch, etc… let us know!
Moments. Memories & more from our first two Overland TRAILs (run) in 2022 and 2023. We are grateful to witness this event grow!
As seen through singular frames pulled from a couple of our cinema cameras out on course. We hope that you enjoy this visual memories as much as we do!
Help us support Vermont’s flood recovery efforts. We created this VERMONT STRONG Art Poster in hopes of encouraging our audience to help us support the local highway departments, fire departments, and emergency service departments in each town that our race courses go through.
Through September 1st, 2023, 100% of profits from the sales of this artwork will be donated to those departments in those towns.
We’re excited to expand and improve upon our offerings to women registered for The Overland! What used to be our Overland Women’s Weekend has been converted into a comprehensive online course, live webinar, and event-day pace groups. All are welcome. Those who are interested should keep reading and sign up!
With Registration Day coming up FAST, we wanted to update you on how we’re moving forward this coming year. Please give our info and updates below some thoughtful consideration.
The real reason for this post is somewhat against the grain and isn’t related to bikes. If you follow me on Strava, you’ll know that over the past couple of years I’ve fallen in love with running.
“Community” – a feeling of fellowship with others, as a result of sharing common attitudes, interests, and goals.
It’s a word that I feel has been overused lately, but when I sat down to write this letter, I couldn’t find a better one to describe what the Vermont Overland brand has turned out to be. I’m honored to be writing to all of you within The Overland community because it has allowed me to reflect on what has not only been a transformative year but what also makes VO so special in the first place.
"Vermont Overland 2021 – A New Era." It's a headline we couldn't have predicted, yet is so fitting. Vermont Overland had an epic year with our community to thank. As we look ahead to what's next, we can't help but reminisce about the fantastic year we've had.
Folks, it’s an honor to be writing this letter. This marks the first of a series of important pre-event communications designed to give you all the information you need to enjoy The Overland 2021!!! We pride ourselves on NOT constantly spamming your inbox, so please, do us a favor, grab a cup of coffee, sit down, and REALLY READ THIS THING.
Vermont Overland’s mission is to promote adventure travel in the state of Vermont, and to appreciate and support the communities that support us. This is our Code of Conduct.
I hope this letter finds everyone well and excited about a NEW YEAR. It goes without saying that 2020 was rough on a lot of fronts. This is the first direct communication that I’ve made with the Vermont Overland community, and I want to personally thank you for staying positive, rolling with the punches, and keeping the stoke high for when we can all gather again. I’m excited to see where we can take Vermont Overland in the years to come.
Vermont Overland BIKE (cycling) – August 15th, 2026
Vermont Overland RUN (running) – August 16th, 2026
Vermont Overland BIKE
August 15th, 2026
Our original event and the biggest of the bunch. The Overland is a 55-mile dirt road bicycle race featuring 7,000 feet of climbing, eight sectors of Class-4 Roads (unmaintained ancient public roads), two well-fortified 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 both the Reading/West Windsor Food Shelf, Ascutney Outdoors, and WAMBA–integral organizations in the event’s host town of Reading/West Windsor/Woodstock.
Vermont Overland RUN
August 16th, 2026
We got our start by believing in the transformative power of all-surface exploration. It’s the best way to race, run, ride, and ultimately experience a landscape. This is our first running-specific event and it certainly won’t be our last.
This is not a half marathon. This is not a Ultra. It’s something completely different. Challenge yourself over 14(ish) miles and 2,500ft(ish) across an all-surface course covering the best of the best in West Windsor, VT.
This event raises funds for both Ascutney Outdoors and Ascutney Trails Association.
Vermont Overland TROPHY
August 15th–16th, 2026 (combined events)
More sports are better than one. Challenge ignites growth. Physical and physiological boundaries are meant to be broken. The Overland TROPHY is all about being a well-rounded athlete with the ability to traverse a landscape efficiently no matter the mode. We want this to challenge you, push your boundaries, and discover the fun in each unique sport.
The Vermont Overland TROPHY is a combined competition for runners & riders competing in both BIKE & RUN events.
Vermont Overland was founded in the belief of transformative all-surface exploration. We truly believe that it’s the best way to race, run, ride, and ultimately experience a landscape.
With Overland Registration Day approaching on January 1st, 2024, at 9 AM, we wanted to reflect on 10 years of memorable Overland’s and look forward to many more to come. THANK YOU for being part of the adventure.
This is a look back on 10 years of Vermont Overland. We hope that you enjoy.