Century Rides in Vermont
The comprehensive 2026 directory of 100-mile centuries, metric centuries (62 miles), and endurance cycling tours across Vermont.
Cycling in Vermont: Terrain & Route Overview
Vermont is cycling perfection for riders who appreciate pastoral charm, rolling green hills, and quiet country blacktops. The Green Mountains bisect the state, offering classic mountain pass ascents known locally as 'gaps'—including Appalachian Gap, Middlebury Gap, and Lincoln Gap, which features the steepest paved mile in the United States. Century routes like the Green Mountain Century and local cycling festivals weave past iconic red barns, covered bridges, artisan cheese farms, and flowing trout streams. Autumn in Vermont brings legendary foliage, drawing cyclists from across the world to ride beneath glowing canopies of sugar maples. Smooth secondary roads, light traffic, and locally sourced finish festivals make Vermont an absolute masterpiece for century cycling.
Terrain Characteristics: Green Mountain alpine passes, scenic river valleys, rolling dairy farm lanes, and historic covered bridges.
Riding Season & Weather: May through October.
📍 Vermont Century Rides Map
5 Plotted EventsPeacham Fall Fondo
📅 Sep 25, 2027More information can be found at peachamfallfondo.com as partners and sponsors are solidified in the coming months. The 2026 Event Guide is linked at the bottom of the page there for perspective on how our event functions – every year is a little different, but every year involves gorgeous gravel, tasty pie, and some degree of foliage! We have not yet identified our featured beneficiary for 2027. Please email...
⚡ Event Details & Specifications ›
| Dataset Population | 2027 Forward Calendar |
| Qualified Distances | ⚡ Half Century (50 mi) |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Sep 25, 2027 |
| Street Address | 79 Church St |
| Location | Peacham, VT 05862 |
| GPS Coordinates | 44.327662, -72.171022 (Google Maps ↗) |
| Organizer | Wahoo Fitness ↗ |
| Entry Fee | $99 |
| Registration | Direct Registration Link ↗ |
The Overland
📅 Aug 15 – 16, 2026The Overland is an invitation to go beyond what’s charted, to explore Vermont’s hidden public corridors, appreciate all this beautiful state has to offer and to rediscover what adventure really feels like.
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Qualified Distances | 🏔️ Imperial Century (100 mi)⏱️ Metric Century (62 mi)🗺️ RWGPS Map (2) |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Aug 15 – 16, 2026 |
| RWGPS Telemetry | Interactive Route Map (2) → • Send to Wahoo/Garmin ↗ • GPX ⬇ • TCX ⬇ |
| End Date | 2026-08-16T00:00:00 |
| Starting Venue | Woodstock, VT |
| Location | Woodstock, VT, VT |
| GPS Coordinates | 43.62482, -72.538455 (Google Maps ↗) |
| Organizer | Vermont Overland ↗ |
| Entry Fee | $0 |
| Registration | Direct Registration Link ↗ |
Unrouted
📅 Nov 01, 2026A checkpoint-style ride to the hidden gems of Chittenden County Here’s the situation, it’s November 1st, the leaves have fallen, the days are getting shorter, but you’re looking for one last adventure ride. Well, your friends at Jericho Dirt have a new type of adventure ride for you, inspired by the LA Tourist events in Southern California. Here’s the deal, there will be a start and finish location, but no set...
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Qualified Distances | ⚡ Half Century (50 mi) |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Nov 01, 2026 |
| Street Address | VT-15 |
| Location | Jericho, VT 05465 |
| GPS Coordinates | 44.507249, -72.988952 (Google Maps ↗) |
| Organizer | Jericho Dirt Events ↗ |
| Entry Fee | $35 |
| Registration | Direct Registration Link ↗ |
Vermont Gran Fondo
SeptemberThe Vermont Gran Fondo is a challenging cycling event that takes place in the beautiful state of Vermont. The event features a variety of routes for all skill levels, including a 100-mile route that takes riders through the picturesque countryside.
⚡ Event Details & Specifications ›
| Dataset Population | Forward Calendar (Schedule Pending) |
| Qualified Distances | 🏔️ Imperial Century (100 mi)🗺️ RWGPS Map (2) |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | September |
| RWGPS Telemetry | Interactive Route Map (2) → • Send to Wahoo/Garmin ↗ • GPX ⬇ • TCX ⬇ |
| Location | Vermont, VT |
| Organizer | VT Gran Fondo ↗ |
Vermont Rare Gravel Ride
📅 Oct 02, 2027Year 13~ Can IT be a Charm! ~Vermont Rare Gravel! Happy to see have you back for another year! You'll see some new, some old and somewhere in between. Keeping it around 45miles this year…they'll be climbing, of course, Class IV, yup! Why not #vermontraregravelride this Year? "Grassroots GRavel" at its Finest! It's not a Race, It's an Adventure! The Hidden Gem of Southern VT Use your GPS - minimal signage...
⚡ Event Details & Specifications ›
| Dataset Population | 2027 Forward Calendar |
| Qualified Distances | ⚡ Half Century (50 mi)🗺️ RWGPS Map |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Oct 02, 2027 |
| RWGPS Telemetry | Interactive Route Map (1) → • Send to Wahoo/Garmin ↗ • GPX ⬇ • TCX ⬇ |
| Street Address | 246 Styles Ln |
| Location | Peru, VT 05152 |
| GPS Coordinates | 43.262736, -72.904967 (Google Maps ↗) |
| Organizer | Fast Fin Productions ↗ |
| Entry Fee | $20 - $80 |
| Registration | Direct Registration Link ↗ |