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TIER 2

Vermont Overland

West Windsor, Vermont (starts at Ascutney Outdoors; course also touches Reading and Woodstock) · 2026: August 15; 2027 date not yet announced

VERDICT Vermont's steepest 55 miles disguised as a pastoral New England postcard.

71
LAB SCORE
[05]

The Ratings

Course verdict

55 miles of Vermont pavé. 7,000 ft elevation. 60% gravel, 30% dirt, 10% pavement.[4]

Course Profile ratings for this race. Select a point for its explanation. LOGISTICS3/5LENGTH2/5TECHNICAL5/5ELEVATION5/5CLIMATE2/5ALTITUDE1/5ADVENTURE5/5 23/35
Course Profile
How the scoring works →
Custom plan

Train for Vermont Overland

A training plan for Vermont Overland—shaped to your fitness and the hours you have.

[01]

Course Overview

OG gravel since 2009—55 miles of Vermont pavé, 7,000 feet of climbing, and Paris-Roubaix dirt roads.

55 mi
Distance
7,000 ft
Elevation
West Windsor, Vermont (starts at Ascutney Outdoors; course also touches Reading and Woodstock)
Location
August 15; 2027 date not yet announced, 2026
Date
~1,000
Field Size
$100-$150
Entry Cost
MORE IN VERMONT: Rasputitsa · Rooted Vermont
Facts & History

Vermont Overland founded 2009. One of oldest US gravel events. Vermont pavé—8 sectors of Class 4 rough unmaintained roads. Capped at 1,000 riders. Starts at Ascutney Outdoors in West Windsor, near Woodstock. Founded in 2009. By Peter Vollers.

Reputation: OG gravel (founded 2009). Vermont pavé character. Technical terrain.

2009: Founded—one of oldest US gravel events
2023: Perfect conditions (60-75°F)
2024: Warm, humid (65-80°F)
[03]

The Course

First-person view from cyclist handlebars riding on dirt gravel road through rural Vermont countryside with green fields and trees - Vermont Overland - Woodstock, VermontPhoto: YouTube / Sean Mauceri
Cyclist's perspective riding gravel road with both hands on handlebars through Vermont farmland with open fields and scattered trees - Vermont Overland - Woodstock, VermontPhoto: YouTube / Sean Mauceri

55 miles of Vermont pavé. 7,000 ft elevation. 60% gravel, 30% dirt, 10% pavement. 8 sectors of Class 4 rough unmaintained roads. Technical rating: 4/5.

Signature challenge: 7,000 ft elevation over 55 miles = relentless. Vermont pavé sectors = technical.

SURFACE COMPOSITION
overall
gravel 60%
dirt 30%
pavement 10%
gravel 60%dirt 30%pavement 10%
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MILE
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MILE
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MILE
RIDERS REPORT
Wade's Field Gap MI 33
First climb of the day starting at 3,000 feet, eight to nine percent grade that gets steeper.
More Town Gap
Gap number two, about eight percent grade climbing, described as a solid climb but not the biggest of the day.
Roxbury Gap
Way too many cars on this road, climbed at about a third of the way up just past 8,000 feet elevation.
Braintree Gap
The biggest question mark of the day with crazy terrain. Technically a dirt road but the dirt is real big, bone jarring, with rocks. Reason people don't ride it too frequently.
Doubleday Hill
Final section described as incredible hell, eighteen to twenty percent grade. Has pavement in beginning but then grass and dirt with some roughs. Called the coolest thing but challenging.
Braintree Gap is technically a dirt road but the dirt is real big, bone jarring with rocks and crazy terrain.
The course is 92% dirt with 77 sections of class four road, which are ancient unmaintained roads in Vermont.
Doubleday Hill has a little bit of pavement in the beginning but then the rest is grass and dirt with some roughs.
[04]

From the Field

The epic 53 mile 92% dirt 77 sections of class four road - these ancient unmaintained roads in Vermont which is just the most unique thing about the race. You come sweeping into the village and make an abrupt right turn onto mechanic street which is this tiny little alleyway brick walls incredibly European incredibly cool.

Peter Vollers · 758 views

Central street is gonna be closed for the day which is pretty groundbreaking here in the village. The village is yours for the day.

Peter Vollers · 758 views

If you're staying here even better because you can just ride right to the course which is really cool, don't even have to get in your car.

Peter Vollers · 758 views
Vermont Overland Grand Prix downtown Woodstock Village start/finish
Peter Vollers · 758 views · 4:51
Vermont Overland Grand Prix 2015 - Available in HD!
Gravel Cyclist · 6.5K views · 6:50
RACER

Racer Reviews

Raced Vermont Overland? Be the first to rate it.
[07]

Training

August 15, 2026 VERMONT OVERLAND
[08]

Train for Vermont Overland

RACE DEMAND PROFILE

Durability
2
Climbing
9
VO2 Power
7
Threshold
6
Technical
10
Heat
1
Altitude
2
Race Specificity
10
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[09]

Race Logistics

Packet Pickup
Day-before. Check official website.
Parking
Free at event site
RIDERS REPORT
Faster riders should line up in the front at the 9 o'clock start, mid range in the middle, slower riders doing it for adventure in the back.
On the finish, if you're with anybody you're going to want to start jockeying for position because the footbridge section is narrow like a hole shot.
[10]

Tire Picks

45mmWET
1
Vittoria Terreno Wet
45mm · $80 · 39W
excellent wet grip
2
Pirelli Cinturato Gravel S
45mm · $74
excellent wet grip
3
Schwalbe G-One Overland
45mm · $70 · 40W
excellent wet grip
NEWS

Latest Coverage

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Similar Races

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Frequently Asked Questions

Historical weather data shows average highs of 78°F and lows of 61°F, with a 60% chance of rain on any given day. August in Vermont can be anything from perfect to swampy hell, and the research shows no historical weather data to plan around. New England summer humidity combined with 7000 feet of climbing is a recipe for heat casualties. No mention of weather incidents probably means they've been lucky, not immune. More weather exposure than Belgian Waffle Ride San Diego.[1]

Ascutney Outdoors provides the venue but Baker Donahue notes the "HUGE corral" with 300-400 riders backed up from the start line. Registration opens January 1st at 9 AM through Movemint and sells out in hours with a 1000-rider cap. Critical details like packet pickup and parking remain undisclosed, though the race benefits local Reading/West Windsor organizations.[7]

An "Arenberg Forest" sector as homage to Paris Roubaix, while Sarah Skelly notes progression from 2022 when she "flailed down several of the class IV roads being bucked the entire way" to 2024 confidence: "What was once so feared, was now just familiar riding." The course requires self-navigation with GPS or cue sheets.[9]

Elite riders like Ian Boswell and Tim Johnson participate, with Johnson leading pre-race recon rides covering technical "baby head" trails. The race attracts 300-400 riders in massive corrals and sells out a 1000-rider field in hours. However, the tragic 2022 death of professional Kenyan cyclist Sule Kangangi casts a shadow over the event's reputation. "Peter Vollers has been around the block a few times... Won the NCCA Collegiate National Championships..."[5]

Those eight Class 4 sectors will humble anyone who shows up thinking this is a leaf-peeping tour. You need solid climbing legs for 7000 feet of punishment and bike handling skills for unmaintained roads that range from sketchy to bike-breaking. The 1000-rider field sells out in hours because riders who've done it know something the rest of us don't.

[11]

Sources & Citations

Research sources used to build this race profile. Always verify details with official race sources before making travel or registration decisions.

  1. Route Maps RideWithGPS: VT - Vermont Overland 2021 (UNVERIFIED/stale)ridewithgps.com/routes/37223600
  2. Community Redditreddit.com/r/gravelcycling/comments/vermont-overland
  3. Other Sources Strambeccostrambecco.com/event/vermont-overland/
  4. Media & Press Velovelo.outsideonline.com/gravel/gravel-racing/gallery-joy-o...
  5. Media & Press CX Magazinewww.cxmagazine.com/2016-vermont-overland-photos-report-pe...
  6. Media & Press Gravel Cyclistwww.gravelcyclist.com/race-reports/vermont-overland-grand...
  7. Community Redditwww.reddit.com/r/gravelcycling/comments/1c4n7si/vermont_o...
  8. Community Redditwww.reddit.com/r/gravelcycling/comments/x0liee/finished_v...
  9. Community Redditwww.reddit.com/r/gravelcycling/comments/xlynan/the_vermon...
  10. Community Redditwww.reddit.com/r/overlanding/comments/1okd3f/vermont_over...
  11. Community Redditwww.reddit.com/r/vermont/comments/12hmhgh/community_for_o...
  12. Other Sources Tobedeterminedwww.tobedetermined.cc/journal/race-report-the-vermont-ove...
  13. Other Sources Vermontoverlandwww.vermontoverland.com/overland/
  14. Community uvcc.bike: Vt Overland Measure Personal Progressuvcc.bike/articles/vt-overland-measure-personal-progress
  15. Community outsideonline.com: Sule Kangangi Of Team Amani Tragically Dies At 33www.outsideonline.com/outdoor-adventure/biking/sule-kanga...