We promote adventure travel.

Register for The Overland Run

Register for The Overland Bike

Register for both and compete in The OVERLAND TROPHY

WebRes-VO-Tom-Batch3-24.JPG

About Us

Welcome to Vermont Overland, where your passion for adventure travel meets the Green Mountain State’s love for enveloping you in lush beauty, crisp air, incredible food and drink and thrilling backcountry travel on a vast network of ancient roads rich with history and unparalleled scenery.

We promote a variety of gravel and adventure cycling/running events every year. Our passion is sharing the spirit of adventure and making it possible for people to go and explore Vermont on their own. 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.

 

The latest happenings.

 
 

Get the goods.

 
 

Our Events

Overland TRAIL (running) – May 10th, 2025

The Overland (cycling) – August 24th, 2024

ScreenGrabs_Vermont_Overland_gravel_race_trail_running_Events.03_11_44_19.Still028.jpg
 

The Overland TRAIL (run)

May 10-11th, 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.

 

The Overland (bike)

August 24, 2024

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.