Century Rides in Virginia
The comprehensive 2026 directory of 100-mile centuries, metric centuries (62 miles), and endurance cycling tours across Virginia.
Cycling in Virginia: Terrain & Route Overview
Virginia offers an extraordinary mix of American history, rolling pastoral beauty, and monumental mountain passes. The Shenandoah Valley and Blue Ridge Mountains provide iconic riding along Skyline Drive and the Blue Ridge Parkway, where century cyclists can soak in panoramic ridge-line views and long, rewarding descents. In central Virginia, routes loop through manicured horse country, historic battlefields, and thriving vineyards around Charlottesville. To the east, flat coastal plains along the Chesapeake Bay offer wind-assisted speed and seaside views. Classic events like the Shenandoah Fall Foliage Bike Festival and local century rides celebrate the state's deep cycling traditions. With rich heritage and diverse geography, Virginia is a premier East Coast century riding state.
Terrain Characteristics: Blue Ridge & Shenandoah mountain crests, rolling Piedmont vineyards, and Chesapeake coastal flats.
Riding Season & Weather: April through June & September through November.
📍 Virginia Century Rides Map
14 Plotted EventsAlpine Loop Gran Fondo
OctoberA classic cycling event with a meaningful charitable connection, presented by the Cancer Journeys Foundation. Mountains worthy of a grand tour, with the character and grit of a classic.
Back of the Dragon
JuneAn iconic ride tackling Route 16 over multiple mountain passes with hundreds of curves and high-elevation elevation gains.
Cap2Cap
MayThe Cap2Cap is the annual bike ride fundraiser for the Virginia Capital Trail Foundation, featuring four distance options along the scenic and historic Virginia Capital Trail.
Civil War Century
SeptemberChallenging century and metric century rides traversing historic battlegrounds
Colonial Virginia Metric Century
OctoberScenic 100 km metric century exploring historic routes
Culpeper Cycling Century
OctoberCulpeper Cycling Century event description not provided.
Culpeper Cycling Century and Tour
OctoberExperience the breathtaking beauty of Culpeper County on this 100-mile, 65-mile, or 35-mile cycling event, with route options tailored for every level of cyclist.
Eastern Shore Metric Century
AprilA flat 100 km (metric century) coastal tour exploring the farmlands
Mountains of Misery
MayNotoriously punishing climbing challenge offering imperial century and double metric routes finishing atop Mountain Lake.
Reston Century
AugustPopular Northern Virginia event featuring 100-mile and metric century loops through Loudoun County's scenic country roads and horse farms.
Shenandoah Valley Century Ride
September1-2 sentence compelling summary of route and event
Storming of Thunder Ridge
MayA premier mountain challenge offering imperial century
Surry Century Ride
SeptemberFlat and rolling coastal routes offering metric and full 100-mile century options through peanut and timber country south of the James River.
Tour de Madison
MayThe Tour de Madison is an annual cycling event held in Madison, Virginia, benefiting the Madison County Parks and Recreation Authority. The event features three route options: a Metric Century (65 miles), an Intermediate Route (45 miles), and a relaxed Family Ride, which can be as long or short as desired.