SCHEDULE OF EVENTS

Friday 8/22/2025

  • 4:00 pm – Camping Opens! Come check in at Ascutney Outdoors and pick up your camping pass (if you ordered one through RunReg).

  • 4:00 to 7:30 pm – Runner sign-in and number pick-up at Ascutney Outdoors! You can grab your number, hang out and enjoy food/drink with our partners and vendors. The Brownsville Butcher & Pantry will be cooking up a feast.

  • 5:00 pm – Shakeout run led by Tracksmith & Northwoods Athletics! We’ll do a short portion of the course starting and finishing from Ascutney Outdoors.

  • 7:00 pm – Bonfire & S’mores hosted by Thule & Northwoods Athletics! (weather permitting…)

  • 10:00 pm – lights out!!!

Saturday 8/23/2025

  • 7:00 am – Find THULE in the vendor zone for FREE COFFEE! The Brownsville Butcher & Pantry also serves a killer breakfast!

  • 7:00 to 8:45 am – Runner sign-in and number pick-up at Ascutney Outdoors.

  • 8:50 to 8:55 am – Call to staging and pre-race announcements.

  • 9:00 am – RACE STARTS! Good luck and enjoy the trail!

  • 11:30 am to 3:00 pm – Post-race party and lunch served by The Brownsville Butcher & Pantry at Ascutney Outdoors. Stick around after the race, grab a bite to eat (included in your entry) and cheer on other Overland TRAIL finishers!

  • 2:00 pm – Awards presented by Tracksmith & THULE at Ascutney Outdoors!

  • 4:00 pm – Final runners finish and clean up… care to help?!? (:

Courses:

…check back in 2025 for our official Overland TRAIL course!

Course Markings and Navigation:

PLEASE study the routes above on Ride with GPS or Strava 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 Arrows = 6-mile Overland PATH

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

Race Rules

  • All runners participating in the TRAIL 15-mile course MUST start with a water flask, bottle, belt, or hydration pack! It is required and we may be disqualifying runners who break this rule.

  • All runners must register online and then sign-in and pick up their bib number on Friday evening or Saturday morning prior to the race start in person. There is no same-day sign-up.

  • This is a cup-less race! Please plan accordingly and bring a water flask, bottle or hydration pack to refill at the Aid Stations.

  • Absolutely no littering. If you pack it in, you pack it out.

  • Absolutely no cutting the course unless you’re dropping out due to an emergency.

  • Horses have the right of way. West Windsor has a large equestrian community. If you see a horse, give it space, and say HELLO!

  • This race takes place on trails and roads that are open to the public. They are not closed for the race so please run against traffic when possible and be cautious and courteous with everyone you encounter.

  • Runners that abandon the race are required to check back in and notify The Vermont Overland team and 802-timing.

  • Well-behaved dogs are welcome to run the 6-mile PATH course but ONLY if they’re leashed and you carry ample extra water for them. Runners with dogs assume 100% risk and liability for themselves, their dog, and those running around them. Dogs are not allowed to run the 15-mile TRAIL course.

  • All runners are required to sign and follow our Vermont Overland Code of Conduct provided in pre-registration!

  • Most importantly, have fun!

Awards:

  • $5,000 in cash prizes split evenly for men/women (15-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 1:00 pm and the breakdown is as follows:

      • 1st – $1,250

      • 2nd – $750

      • 3rd – $250

      • 4th – $150

      • 5th – $100

  • Tracksmith and THULE Gear for the top three men/women (both 15-mile Overland TRAIL and 5-mile Overland PATH)

  • The award ceremony will recognize only the top three overall men/women in each event. We will not be doing podiums for age categories but these categories will be listed in the results at 802 Timing.

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 miles) with course markings.

  • Pre-race camping. Absolutely! We’ll have options for car camping and tent camping at Ascutney Outdoors for folks who pre-registered through RunReg. Once it opens, just come and set up shop.

  • 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.

  • And to reward everyone, we’ll have a huge post-run party with local food (included in your entry!) from The Brownsville Butcher and Pantry.

 

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 and 1 Water Stop for the 15-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 your entry to anyone you know and then easily transfer your entry to them. You can also automatically transfer your spot to the next person in line on the waitlist through Movemint. The deadline to transfer is May 10th, 2024. Thank you for understanding!

  • 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.