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
4 Plotted EventsMad River Valley Century
AugustScenic tour through picturesque farm meadows, historic covered bridges, and swimming holes along the Mad River.
The Irreverent Road Ride (IRR)
JuneMixed-surface century over Vermont's famous dirt gap roads, notch climbs, and scenic backwoods.
The Overland
AugustVermont Overland was founded in the belief that all-surface exploration is transformative. We host trail running and gravel cycling events with the goal of sharing the spirit of adventure while supporting the local communities of Vermont that make outdoor recreation possible.
Vermont Gran Fondo (VTGF)
JuneNotorious alpine climbing challenge conquering the legendary gap roads: Lincoln Gap, Appalachian Gap, Roxbury, and Middlebury.