The Overland 2022 – Registration Day is Coming!

“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.

Our common attitudes toward leaving a place better than we find it, fostering camaraderie, positively stoked energy, and the vital role that health and the beautiful outdoors play in all our lives no doubt align.

Our common interests in making events like this more accessible to women, supporting the next generation of youth cyclists, finding the next gnarly class-4 road, and growing the sport in a sustainable way as a whole remain strong.

And our common goals, to make events like this sustainable for the long haul, by supporting charities, towns, and organizations. This is the standard that allows us to move forward with joy and goodwill.

Why am I making you read a longer than typical VO newsletter? It’s to say thank you. Thank you for being part of the community, for being brave enough to compete in The Overland, and for entrusting me with what’s next.

So, what IS next?

  • The Overland registration day! It’s coming up soon on January 1st at 10 AM. We’re old school and are yet to be converted to the big event lottery sign-up, so if you want one or more of the 1500 available spots, we recommend that you’re ready to go with your BikeReg account dialed once it opens! It sells out FAST. Register here.

  • Race day for The Overland moves to Saturday, August 27, 2022. With The Overland historically being on a Sunday, we found that a large number of participants were rushed to get home, thus minimizing the post-ride party vibes. By moving the race to Saturday we hope to double down and maximize the celebration of all things Overland with even more live music, food, drink, and camping.

  • We are saying goodbye to VOMAR - the Vermont Overland Maple Adventure ride and hello to a couple of other areas of sport. In an effort to minimize the number of large events in the Town of West Windsor, we’ve decided to focus on The Overland in August moving forward while branching out into some other fun and challenging areas of sport, these being running and backcountry skiing. We are confident that it will help keep all events in the West Windsor area more sustainable. Information will be forthcoming regarding running and backcountry skiing. Stay tuned!

  • Expanded and FREE women’s preview rides throughout 2022. Stay tuned for details. We are stoked!

Other minor things to note:

  • In an effort to minimize waste and accurately predict how many event hats we need to order, we’ve made it separate from event registration. If you want a coveted Vermont Overland cap (the color changes every year), it must be purchased in addition to your entry. This can be done easily through BikeReg at any time.  

  • There are limited camping spots at Ascutney Outdoors! To keep numbers accurate in accordance with our venue and the town, camping spots need to be purchased separately from your entry. This can also be done easily through BikeReg.

  • Check out our latest uploads, from the 2021 Overland. These include event Videos and rider testimonials among other goofiness. It can all be seen on the Vermont Overland YouTube channel here.


All the best everyone - happy holidays, and cheers to consistent training!


Ansel Dickey

Owner/Director - Vermont Overland

Ansel Dickey