We promote adventure travel.

Register for Overland Run (event date: August 23rd, 2025)

Register for Overland Bike (event date: August 24th, 2025)

Register for both and compete in The OVERLAND TROPHY (event dates: August 23-24th, 2025)

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About Us

Vermont Overland was founded in the belief that all-surface exploration is transformative.

Today we still host our flagship event, The Overland (bike) & The Overland (run), along with many other smaller events with the goal of sharing the spirit of adventure while also supporting the local communities of Vermont that make these events possible.

Be sure to follow us on YouTube, Instagram, Facebook and Strava to join the party. Also, subscribe to our email list below for updates and info as our events tend to sell out within minutes.

 
 

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Our Events

Overland Run (running) – August 23rd, 2025

Overland Bike (cycling) – August 24th, 2025

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Overland Run

August 23rd, 2025

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 a Ultra. It’s something completely different. Challenge yourself over 15(ish) miles and 3,300ft(ish) 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.

Overland Bike

August 24th, 2025

Our original event and the biggest of the bunch. The Overland is a 55-mile dirt road bicycle race featuring 7,000 feet of climbing, eight sectors of Class-4 Roads (unmaintained ancient public roads), two well-fortified sag stops, a magnificently scenic route and an awesome party afterwards.  It’s the ultimate overland adventure ride.   Open dirt roads, amazing scenery and an epic course unlike any you’ve ever ridden before, all within a beautiful Vermont pastoral setting.

The purpose of this race is to promote the wonderful world of overland adventure riding and to benefit both the Reading/West Windsor Food Shelf, Ascutney Outdoors, and WAMBA–integral organizations in the event’s host town of Reading/West Windsor/Woodstock.