The Overland Trail
The Overland Trail: a challenging 15-mile all-surface race with 2,500 feet of climbing in Vermont's hills.
Race Date
Aug 16, 2026
Location
Brownsville, VT
Quick facts
- Date
- Sunday, August 16, 2026
- Location
- Brownsville, Vermont
- Distance
- Half marathon (13.1 mi) + 5 Miles, 15 Miles
- Course
- Loop Course
- Terrain
- Trail
- USATF certified
- Not listed
Highlights
Good For
Atmosphere
Course
The Experience
The Overland Trail isn't your standard half marathon. This 15-mile all-surface challenge climbs nearly 2,500 feet through the hills of West Windsor, Vermont, starting and finishing at Ascutney Outdoors. Racers tackle a mix of trail, dirt, and gravel – a true all-surface experience designed to showcase the region's best terrain.
This first running-specific event from the organizer (who believes in the transformative power of all-surface exploration) puts a premium on grit and scenery. The course covers the best of the best of West Windsor, sweeping through forests and over hills with mountain views. With a field limited to 1,000 runners, the atmosphere is intimate and community-focused.
Proceeds benefit Ascutney Outdoors and Ascutney Trails Association, so every step supports the trails you're running. The 9 AM mass start on a Sunday morning in August kicks off a day of challenge and reward. This is a race for those who want something different – a genuine trail test with a hometown heart.
Race-provided description
We got our start by believing in the transformative power of all-surface exploration. It’s the best way to race, run, ride, and ultimately experience a landscape. This is our first running-specific event and it certainly won’t be our last. This is not a half marathon. This is not an Ultra. It’s something completely different. Challenge yourself over 15 miles and close to 2,500ft across an all-surface course covering the best of the best in West Windsor, VT. This event raises funds for both Ascutney Outdoors and Ascutney Trails Association.
Logistics
Race Day
Sunday, August 16, 2026
Start Time
9:00 AM
Start Location
449 Ski Tow Rd, Brownsville, VT, 05037
Course Info
Course Type
Loop Course
Terrain
trail
Scenery
Forest, Mountain
Difficulty
Hilly
Net Drop/km
0 m (Flat)
Separation
0.0%
Also Offers
Quality Score
first year
no finisher counts yet
small race — neutral
needs a few years of results
3 timing sources
no finisher data yet
no winner time yet
typical high 77°F
Race Day Weather
5-year historical avgStart (Low)
58°
Afternoon (High)
77°
Warm — hydration strategy is key, start conservatively
0.1"
Precipitation
8 mph
Wind
78%
Humidity
Frequently asked
When is the The Overland Trail?
The The Overland Trail is held on Sunday, August 16, 2026, starting at 9:00 AM.
Where does the The Overland Trail take place?
It takes place in Brownsville, Vermont.
What distances does the The Overland Trail offer?
The half marathon (13.1 miles), plus 5 Miles, 15 Miles.
Is the The Overland Trail course flat and good for a PR?
The The Overland Trail is a hilly, loop course course.
HalfRuns editorial — independent, no paid placement.
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