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 purchased one through Movemint).

  • 4:00 to 7:00 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. Spice Spoke 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 – Campers & early risers: find THULE in the vendor zone for FREE COFFEE! (limited supplies, served until we run out)

  • 7:00 to 9:45 am – Runner sign-in and number pick-up at Ascutney Outdoors.

  • 9:50 to 9:55 am – Call to staging and pre-race announcements.

  • 10:00 am – The Overland RUN: race mass start! Good luck and enjoy the trail!

  • 11:30 am to 3:00 pm – Post-race 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!

  • 12:00 to 8:00 pm – Vendor zone & pre-registration party for The Overland BIKE! RIDERS: COME GRAB YOUR NUMBER EARLY! Enjoy live music from Johnny Spompinato & The Value Leaders, Wood Fired Pizza from The Brownsville Butcher & Pantry, and noodle bowls from The Spicy Spoke! Good vibes all-around and lot’s to do in the vendor zone with: Specialized, Thule, Ko–INEOS Grenadier, Tracksmith, Julbo, Untapped Maple, Velocio, Class4 Designs, Paradis Sport, EF Adventures, Athletic Brewing, Fiddlehead Brewing, Shacksbury Cider, and more!

  • 3:30 pm – Awards presented by Tracksmith & THULE at Ascutney Outdoors!

  • 5:00 pm – Wahoo Mountain Mile hosted by Northwoods Athletics! This is a free and fun run up and down the J-bar at Ascutney Outdoors with prizes from Wahoo & Julbo. All are encouraged and all are welcome! Sign the waiver at registration.

  • 5:30 pm – CHARITABLE RAFFLE with awesome prizes from THULE, Wahoo and Specialized. Tickets can be purchased at registration and are $10 each. 100% of proceeds for to Ascutney Outdoors. Winning numbers will be drawn after the finish of the Wahoo Mountain Mile in the vendor zone. This is an old-school raffle with a max of 3 number reads per ticket –– you must be present to win!

  • 6:00 to 8:00 pm – Live music headliner: Jonny Spompinato & The Value Leaders! These guys are coming all all the way from Cape Cod, MA, to play for Vermont Overland 2025!

  • 9:00 pm – Lights out!

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 8:45 am – Enjoy free coffee from Black Magic Coffee 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 8:45 am – Number pick-up and rider sign-in at the Ascutney Outdoors Center.

  • 9:00 am – OVERLAND BIKE 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!

Courses:

The Overland TRAIL (long course)

  • 14 miles

  • 2,300ft 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 2025 ROUTE (TRAIL course)

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

The Overland PATH (short course)

  • 5 miles

  • 750ft of elevation gain (give or take a little…)

  • 2 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 2025 ROUTE (PATH course)

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

Course Markings and Navigation:

PLEASE study the routes above on 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 = 14-mile Overland TRAIL

  • Turquoise Arrows = 5-mile Overland PATH

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



Race Rules

  • All runners participating in the TRAIL 14-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 5-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 14-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 (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 1:00 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 14-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 on Movemint or 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 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 23, 2025. Thank you for understanding! Our full refund policy can be read here.

  • 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.