Schedule of events
Friday 8/22/2025
Early comers welcome! Enjoy MTB trails at Ascutney Outdoors, endless gravel roads, food and drink at the Brownsville Butcher and Pantry. Preview the course at your convenience by using Ride with GPS.
4:00 pm – Camping opens! Come check-in, pick up your camping pass, and claim your spot at the Ascutney Outdoors Center and set up camp for the weekend. Spots are allocated on a first come first serve basis. (Please note that camping at Ascutney is saved for those who reserved their spots on BikeReg, this is no Burning Man...)
Saturday 8/23/2025
9:00 am to 2:00 pm – The Overland (run) – RACE DAY! We welcome cyclists to come early and spectate this now iconic 15 mile Vermont trail run.
12:00 to 8:00 pm – Expo/vendor zone opens! Come hang with out friends from Specialized Bicycles, THULE, KO Ineos Grenadier, Class4 Designs, Julbo, Untapped Maple, OVRLND.studio and more.
6:00 pm – Wahoo Mountain Mile hosted by Northwoods Athletics! Anyone is welcome to join this short trail run and those who are brave enough will get a free beverage and a chance to win prizes from Wahoo.
4:00 to 8:00 pm – Race number pickup party with The Brownsville Butcher & Pantry at Ascutney Outdoors with live music!
7:30 pm – S’mores and fun with Specialized & THULE.
Sunday 8/24/2025
6:00 am –The parking rush begins! CARPOOL. CARPOOL. CARPOOL. Arrive early, and listen to our parking volunteers!
7:00 to 9:30 am – Enjoy free coffee from Carrier Roasting served by THULE as well as baked goods, and breakfast burritos for sale from The Brownsville Butcher & Pantry at Ascutney Outdoors! First come first serve a la carte.
7:00 to 9:45 am – Number pick-up and at the race venue at the Ascutney Outdoors Center.
9:00 am – OVERLAND MASS START (neutral rollout for the first 1.5 miles)
1:00 to 8:00 pm – Post-RIDE Party & Cookout with The Brownsville Butcher & Pantry.
3:30 pm – Podium ceremony near the finish line. (Top three overall women, non-binary, and men only. No age groups.)
5:00 pm – Venue clean up... care to help??? (:
6:00 pm – camping closes!
The course: Overland (bike) 2025
General Course Info
We typically release the course to our participant list around 7-14 days ahead of the event.
55.6 miles
7,000ft of elevation gain (give or take a little…)
7-8 Class4 unmaintained road sectors
2 Aid Stations
SELF NAV! We have been conducting a self-navigated gravel event for 7 years in a row now. Please come prepared with the route pre-dowloaded to our bicycle computer, or printed cue sheets in your pocket.
Notes
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. Experience what it’s like to ride your bike on roads that are not only incredibly beautiful but are, most importantly, largely free of hostile car traffic. Throw in some ancient unmaintained roads for technical challenge and the real adventure begins!
The Overland is an open ride so anyone can enter. From the more aggressive riders gunning for the win to the local biker out for the challenge, everyone will start together. The riders will embark at 10 am sharp on the amazingly picturesque “ronde” course meandering through some of the most lovely Vermont countryside.
Pre-race camping. Absolutely! We’ll have options for car camping and tent camping at and around Ascutney Outdoors. Please be sure to register for a spot on Movemint and pick up your camping pass at Ascutney Outdoors.
Class-4 is the name of the game. These are Vermont’s unmaintained legal throughways, or old town roads. Some are mellow, some are not. The Overland overall is a very challenging ride that requires good technical skills on a bike - please come prepared with the correct equipment, skill level and fitness!
Riders will be treated to two awesome sag stops.
And to reward everyone, we’ll have a huge post-ride party with local food and craft beer (included in your entry!) from Brownsville Butcher and Pantry!
FAQ:
Where’s the start/finish, parking and registration? Everything is located at the race venue at Ascutney Outdoors. Race starts promptly at 10 am. Neutral start for the 1st mile.
Will there be camping near the venue? Absolutely! You can sign up for camping on our BikeReg page. Limited spots are available.
Where can I stay? There’s a variety of local hotels in the area (listed below), but if you want our opinion, just freaking camp! It’s the best experience and you’ll be right in the center of all the action.
What kind of bike race is this? Road race? Cross race? Mountain bike race? It’s a little bit of all three. It’s an overland bike race.
What percentage of the course is dirt? About 95%. The pavement sections are purely transitional and no longer than a kilometer or two in each stretch.
SELF-NAV!!: Vermont Overland strongly feels that the very roots of gravel grinding lie in self and group navigation. Directional signs have such a massive visual impact on the communities through which we ride and race. Further, sign sabotage is real and can ruin your day as a rider (and as a promoter). So download the course to your phone or GPS unit or print out the cue sheet (or both) and have a blast navigating your way around the course with whatever group you end up with! Through our partnership with Ride with GPS, participants have access to the course with custom cues, points of interest, marked segments, aid stations and navigation FOR FREE.
What type of bike is optimal for the Overland: Run what you bring! A cross bike or gravel-specific bike with at least 32c tires and low gearing (at least 1 to 1) will also do nicely. You may need a mountain bike rear derailleur to make it work. For those new to dirt road riding, a hardtail mountain bike is great. Road bikes on as big a tire as you can fit are okay but not optimal. [NB: For those just riding to finish and on the fence between a cross and mt bike, you may want to go with the latter.]
Is there a bike shop in town in case I need to have my bike tuned or pick up a spare tube and CO2? Yes, Route 4 Bikes, located at 30 Central Street, Woodstock will be open and ready for business on Fri and Saturday. Drummond Cycles is also somewhat nearby in Enfield, New Hampshire.
What about COVID-19? The Vermont Overland team is doing everything possible to promote a SAFE event. All registrants are required to know and follow local and state guidelines. Currently, we are following the most recent Vermont State guidelines and ask that all individuals who are un-vaccinated to please wear a mask at the festival, staging area, and food areas when social distancing cannot be maintained. Subsequent communications about COVID-19 and what will be expected on event weekend will be sent out to registrants prior to the event, and may be adjusted accordingly as the COVID-19 situation evolves.
Can I get a refund or deferral? We have a VERY strict no-refund and no-deferral policy. No exceptions. If you wish to give up your spot, you can sell your entry to anyone you know and then easily transfer your entry to them through Movemint. You can also automatically transfer your spot to the next person in line. This only applies if there are people on a waitlist for the category you registered for. Please check before hand! The deadline to transfer is August 23, 2025. Thank you for understanding!
The Overland sold out and I want in…!!! Join the waitlist and cross your fingers that someone can’t make it and sends you their spot, look for an opportunity to get in through one of our limited charity spots when they’re announced, or be sure to register on-time next year on January 1st, 2026!!!