Welcome…

Vermont Overland exists to celebrate effort, community, and the rugged beauty of traversing a landscape under your own will. We have no bureaucratic agenda; we simply hope to inspire movement, adventure, and a deeper appreciation for the places you explore.

What began in 2013 as a small gravel ride through Vermont's forgotten Class 4 roads has grown into a weekend of running, riding, camping, live music, local food, and thousands of people coming together around a shared love of adventure. While a lot has changed over the years, our philosophy hasn't: build challenging and memorable courses, support the communities that host us, leave every place better than we found it, and never lose sight of why we started.

If we've learned one thing after more than a decade of hosting these events, it's that preparation leads to a better adventure. This manual contains everything you need to know before arriving—from schedules, course information, and navigation to safety guidelines, parking, camping, and race-day logistics. Give it a thorough read now so you can spend less time asking questions on event weekend and more time enjoying the experience.

Finally, thank you. Vermont Overland only exists because of the participants who show up ready to challenge themselves, the volunteers who give their time, the landowners and towns who welcome us, our charitable partners, and the brands that believe in everything we do. We're incredibly grateful to have you here.

Now let's go have some fun.

Before you arrive…

  • Download the latest course routes and navigation files.

  • Read the safety information for your event.

  • Double-check parking and camping instructions.

  • Review the weekend schedule so you don't miss the fun.

Schedule of events

Friday, August 14th, 2026 (Expo, bib pick up, food & live music)

  • 2:00 pm – Camping & event expo opens at Ascutney Outdoors.

  • 4:00 pm to 8:00 pm – Runner & rider bib pick up at Ascutney Outdoors.

  • 5:00 to 8:00 pm – Pre-ride party & cookout with The Brownsville Butcher & Pantry.

  • 5:00 pm – Mountain Mile, prizes and more. (free fun run for kids & anyone else brave enough)

  • 6:00 pm – Live music: The Gr8tful Folk with Erik Boedtker

Saturday, August 15th, 2026 (Vermont Overland BIKE)

  • 6:00 am – Parking rush begins! CARPOOL. Arrive early and listen to our parking volunteers! 

  • 6:00 to 8:30 am – Bib pick up at Ascutney Outdoors, free coffee + breakfast items served by THULE. Donations to Ascutney Outdoors appreciated.

  • 9:00 am – RACE START Mass start: everyone starts together. Neutral rollout for the first 1.5 miles.

  • 1:00 to 7:00 pm – Post-ride party & cookout with The Brownsville Butcher & Pantry, Untapped Maple creemees and more. Bib pick up for runners continued. 

  • 4:00 pm – Podium ceremony near the finish line. (top three overall women, men, and NB only)

  • 5:00 pm – Charity raffle with awesome prizes. (Buy tickets at the Vermont Overland merch booth)

  • 6:00 pm – Live Music: Johnny Spampinato & The Value Leaders

  • 8:30 pm – Fireside chat & smores with TRACKSMITH & THULE.

  • 9:30 pm – Lights out! Please respect everyone camping at the venue.

Sunday, August 16th, 2026 (Vermont Overland RUN)

  • 6:00 to 8:30 am – Bib pick up at Ascutney Outdoors, free coffee + breakfast items served by TRACKSMITH. (Donations to Ascutney Outdoors appreciated.)

  • 9:00 am – RACE START.  Mass start: everyone starts together.

  • 12:00 to 3:00 pm – Post-run party & cookout with The Brownsville Butcher & Pantry, Untapped Maple creemees and more.

  • 1:30 pm – Awards ceremony near the finish line. (top 3 women, men, and NB for both race distances & top 3 overall Overland TROPHY only)

  • 4:00 pm – Venue clean up... care to help??? (: 

  • 5:00 pm – camping closes!

Course Info

The Overland TRAIL (long course)

  • 15 miles

  • 2,400ft of elevation gain (give or take a little…)

  • 3 Aid Stations p/b Untapped Maple – please start the run with everything you need to complete it SELF-SUPPORTED! Our Aid Stations are managed by volunteers and should be treated as extra hydration/fuel, but only if you need it.

  • LINK TO OFFICIAL 2026 ROUTE (TRAIL course)

  • LINK TO OFFICIAL TCX and GPX FILES (TRAIL course)

The Overland PATH (short course)

  • 5.5 miles

  • 800ft of elevation gain (give or take a little…)

  • 1 Aid Station p/b Untapped Maple – please start the run with everything you need to complete it SELF-SUPPORTED! Our Aid Stations are managed by volunteers and should be treated as extra hydration/fuel, but only if you need it.

  • LINK TO OFFICIAL 2026 ROUTE (PATH course)

  • LINK TO OFFICIAL TCX and GPX FILES (PATH course)

Course Markings and Navigation

PLEASE study the routes above beforehand. Both courses will be fully marked with directional arrows and Vermont Overland marking flags, but we’re still encouraging runners to bring a GPS or phone with the routes pre-loaded. The directional arrows will be at each trail crossing or intersection and the marking flags will be placed periodically throughout the trails/roads. If you see these flags, you’ll know you’re on course.

  • Orange Arrows = 15-mile Overland TRAIL

  • Turquoise Blue Arrows = 5.5-mile Overland PATH

  • Orange Flags = you’re on course, both TRAIL and PATH

RUN - Race Rules & Safety

  • Cup-free race: Start with everything you think you need to complete the race in a self-sufficient fashion. All runners are required to start with at least 1x re-usable water flask.

  • Open course: Roads remain open to traffic. Follow all course police & marshal instructions, obey traffic laws, and stay alert.

  • Share the trail: Yield when appropriate, be courteous, and respect fellow runners, horses, cyclists, hikers, and motorists.

  • Respect the land: Stay on the marked course and treat every property—public and private—as if it were your own.

  • No outside support: Crew and outside aid are only permitted at designated aid stations.

  • Leave no trace: Pack out everything you bring. If you can pick up someone else's trash, even better.

  • Run safe and within your own control at all times.

  • Don't be lame. Help people. Say thank you. Smile often. Have fun.

  • All runners are expected to read and know our rider code of conduct.

Results & Awards:

Individual and age-group results for all races will be available shortly after you finish by the 802 timing trailer near the finish line. They’ll also be posted online shortly after each race is finished. For past years results please visit our website here.

We’ll be recognizing our top three women, men and non-binary runners, riders, and TROPHY seekers overall with prizes from Class IV Designs, Tracksmith, THULE, Suunto, and Wahoo.

Awards will be presented at 4:00 pm on Saturday and 1:30 pm on Sunday near the finish line.

  • $5,000 in cash prizes split evenly for men/women (14-mile Overland TRAIL only).

    • We’re pleased to offer, with the help of Tracksmith, a healthy prize purse for the pointy end of this trail race. The awards ceremony will take place at 1:30 pm and the cash prize breakdown is as follows:

      • 1st – $1,250

      • 2nd – $750

      • 3rd – $250

      • 4th – $150

      • 5th – $100

  • Additional prizes from Suunto, Tracksmith and THULE for the top three men/women (both 15-mile Overland TRAIL and 5.5-mile Overland PATH)

Pre & Post-Race Food

The Brownsville Butcher & Pantry will be serving up an absolute feast all weekend.

  • Friday evening: Wood-Fired Pizza, live music, and more at Ascutney Outdoors. We invite everyone signed up to pick up their race numbers, enjoy some incredible food & drink, and kick off the weekend with us at Ascutney Outdoors. Also: don’t miss the mountain mile (our free fun run) with awesome prizes for kids at 5:00pm.

  • Saturday post-run party (free for riders) 1x beverage and entire food plate from The Brownsville Butcher & Pantry included in your entry. Additional food can be purchased from the BB&P for friends and family on-site.

  • Sunday post-ride party (free for runners) 1x beverage and entire food plate from The Brownsville Butcher & Pantry included in your entry. Additional food can be purchased from the BB&P for friends and family on-site.

The Venue

Camping

We’re excited to expand upon our camping options at Ascutney Outdoors this year! Remember: all campers are expected to be 100% self-sufficient. Pack it in, pack it out.

  • Tent only camping = Space for you and your tent at Ascutney Outdoors – away from your car! This camping option requires you to walk to the tent camping zone with your gear.

  • Car & Tent camping = Space near Ascutney Outdoors, along the treeline in the general parking area, or just North of the venue zone, to camp in or next to your car. We ask that noone take up more space than 1.5 parking spots for this.

  • 4x4 Camping = Space to camp in or next to your car in a meadow about a ¼-mile away from Ascutney Outdoors. PLEASE NOTE – 4x4 vehicles are required to access this field.

  • Camper or small RV = We have a limited amount of space for campers or small-RV's near Ascutney Outdoors. PLEASE NOTE: there are no electrical hook ups and no toilet hook ups. This camping option only reserves you space. Full size RV's are NOT allowed.

  • All camping spots and their respective categories are reserved ahead of time through our event registration pages hosted by Movemint. There are a limited amount of space for all camping categories. You will not be able to purchase additional camping spots on-site.

  • Camping check-in opens at 2pm on Friday. Each camping pass is good for both Friday & Saturday nights.

  • Once arriving at the venue, please come check-in at Ascutney Outdoors to pick up your race number and camping pass.

  • Please study & reference the camping zone map below before you arrive. If you are having trouble finding the different camping zones, we’ll have signs and volunteers to direct you to the different zones.

  • Camping spots in each respective category are self-assigned and allocated on a first-come, first-served basis. Water and portable toilets will be available at Ascutney Outdoors. If you pack it in, you need to pack it out!

  • IMPORTANT: ABSOLUTELY NO CAMPFIRES. We’re very lucky to have Ascutney Outdoors as our host venue and breaking these camping rules would not be good.

  • Once you’re set up, please have your camping passes displayed on the windshield of your vehicle or attached to your tent at all times!

General Notes

  • The purpose of this race is to promote the wonderful world of overland running and to benefit both Ascutney Outdoors and Ascutney Trails Association, both integral organizations in the event’s host town of West Windsor. The trails on and around Mt Ascutney are absolutely amazing and we owe our thanks to these incredible organizations.

  • The Overland TRAIL is an open run so anyone can enter. From pro runners going for the $5k in awards to folks just wanting to find a new challenge, everyone is welcomed and celebrated. Runners will start at 9 AM sharp, all together #OneAdventure style, and go on to complete their respective routes (15 miles or 5.5 miles) with course markings.

  • The format, vibe, and course of The Overland TRAIL is drawing inspiration from our first and most successful event, The OVERLAND gravel bike race. There’s something special about experiencing every kind of surface, road, gravel, trail, unmaintained class-4 roads, etc, in one beautiful route. Sharing that experience with others is what we do here at Vermont Overland.

FAQ:  

  • Where’s the start/finish, parking, camping, and registration? Everything is located at the race venue at Ascutney Outdoors, except for the pre-registration party on Friday evening which will be located right down the road at The Brownsville Butcher & Pantry.

  • Will there be timing? Oh yes. We’ll have the gold standard of timing, 802 Timing, back in action with their live timing screen right at the finish! They’ll also break down results into ten-year age categories for both men and women.

  • Will there be camping near the venue? Absolutely! You can sign up for camping on our RunReg page. Limited spots are available and first come first serve.

  • What kind of run is this? Road race? Cross-country race? Trail race? It’s a little bit of all three. It’s an overland race.

  • What percentage of the course is dirt/trail? About 98%. The pavement sections are purely transitional.

  • Will the course be marked? Yes, absolutely. The course will be fully marked with Vermont Overland directional signs.

  • Will there be Aid Stations? Yes, we’ll have 3 Aid Stations for the 14-mile TRAIL course and 2 Aid Stations for the 5-mile PATH course. Each Aid Station will have water, Untapped Mapple fuel, snack bites, and other treats from The Brownsville Butcher & Pantry among volunteers. PLEASE PLAN YOUR RUN ACCORDINGLY! Even with our Aid Station support, we ask every runner to bring everything they need to make it through the course self-supported.

  • What type of shoe is optimal for The Overland TRAIL? Run what you bring! But any kind of trail shoes would probably do the trick.

  • 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.

  • 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 or gift your entry to anyone you know and then easily transfer your entry to them through Movemint. The deadline to transfer is August 14, 2026. Thank you for understanding! Our full refund policy can be read here.