πŸ‡ΊπŸ‡Έ South Region → β€’ VA

Century Rides in Virginia

The comprehensive 2026 directory of 100-mile centuries, metric centuries (62 miles), and endurance cycling tours across Virginia.

9 Verified Rides
VA State Code
April through June Prime Riding Window

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.

Explore All South Region Century Rides →

πŸ“ Virginia Century Rides Map

9 Plotted Events
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Virginia Century Ride Schedule

Showing 9 organized cycling events

43rd Ken Thompson Reston Century

πŸ“… Aug 23, 2026 (6:30 AM – 5:00 PM)
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)
πŸ“ Reston Town Center West β€’ Reston Town Center West, VA

Join us for the 43rd Ken Thompson Reston Century, a 100-mile ride with various distance options, including a 62-mile metric century and a 31-mile half metric.

🏷️ $60.00, 75.00, 85.00, 95.00, 25.00MetricCentury100M
⚑ Event Details & Specifications ›
Dataset Population2026 Verified Census
Qualified Distances
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… Aug 23, 2026 (6:30 AM – 5:00 PM)
End Date2026-08-23T17:00:00
Starting VenueReston Town Center West
Street Address1950 Opportunity Way
LocationReston Town Center West, VA 20195
GPS Coordinates38.96, -77.3456 (Google Maps β†—)
OrganizerReston Bicycle Club β†—
Entry Fee$60.00, 75.00, 85.00, 95.00, 25.00
RegistrationDirect Registration Link β†—
🏒 Hosted by: Reston Bicycle ClubπŸ“ 1950 Opportunity Way, 20195

Alpine Loop Gran Fondo

πŸ“… Oct 06, 2024 at 8:00 AM
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)πŸ—ΊοΈ RWGPS Map
πŸ“ Downtown Harrisonburg β€’ Harrisonburg, VA

A classic cycling event with a meaningful charitable connection, presented by the Cancer Journeys Foundation

🏷️ $0AlpineMetric Available100M
⚑ Event Details & Specifications ›
Dataset PopulationForward Calendar (Schedule Pending)
Qualified Distances
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)πŸ—ΊοΈ RWGPS Map
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… Oct 06, 2024 at 8:00 AM
RWGPS TelemetryInteractive Route Map (1) → β€’ Send to Wahoo/Garmin β†— β€’ GPX ⬇ β€’ TCX ⬇
End Date2024-10-06T00:00:00
Starting VenueDowntown Harrisonburg
Street AddressHarrisonburg, VA 22801
LocationHarrisonburg, VA 22801
GPS Coordinates38.448864, -78.871438 (Google Maps β†—)
OrganizerBishop Racing LLC β†—
Entry Fee$0
RegistrationDirect Registration Link β†—
🏒 Hosted by: Bishop Racing LLCπŸ“ Harrisonburg, VA 22801, 22801

Cap2Cap

πŸ“… May 08 – 09, 2026
⏱️ Metric Century (62 mi)πŸ—ΊοΈ RWGPS Map
πŸ“ Chickahominy Riverfront Park and Dorey Park β€’ Virginia Capital Trail, VA

The Cap2Cap is the annual bike ride fundraiser for the Virginia Capital Trail Foundation, featuring four distance options, fully supported course, party zones, and breathtaking scenery.

🏷️ $0Metric CenturyFundraiserSupportedParty Zones
⚑ Event Details & Specifications ›
Dataset Population2026 Verified Census
Qualified Distances
⏱️ Metric Century (62 mi)πŸ—ΊοΈ RWGPS Map
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… May 08 – 09, 2026
RWGPS TelemetryInteractive Route Map (1) → β€’ Send to Wahoo/Garmin β†— β€’ GPX ⬇ β€’ TCX ⬇
End Date2026-05-09T00:00:00
Starting VenueChickahominy Riverfront Park and Dorey Park
LocationVirginia Capital Trail, VA
GPS Coordinates37.5594, -77.4472 (Google Maps β†—)
OrganizerVirginia Capital Trail Foundation β†—
Entry Fee$0
RegistrationDirect Registration Link β†—
🏒 Hosted by: Virginia Capital Trail Foundation

Culpeper Cycling Century

πŸ“… Oct 03, 2026
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)πŸ—ΊοΈ RWGPS Map
πŸ“ Lenn Park β€’ Lenn Park, VA

Culpeper Cycling Century

🏷️ $0Metric Available100M
⚑ Event Details & Specifications ›
Dataset Population2026 Verified Census
Qualified Distances
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)πŸ—ΊοΈ RWGPS Map
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… Oct 03, 2026
RWGPS TelemetryInteractive Route Map (1) → β€’ Send to Wahoo/Garmin β†— β€’ GPX ⬇ β€’ TCX ⬇
Starting VenueLenn Park
LocationLenn Park, VA
GPS Coordinates37.431573, -78.656894 (Google Maps β†—)
OrganizerCycling Virginia β†—
Entry Fee$0
RegistrationDirect Registration Link β†—
🏒 Hosted by: Cycling Virginia

Culpeper Cycling Century and Tour

πŸ“… Oct 03, 2026
πŸ”οΈ Imperial Century (100 mi)
πŸ“ Lenn Park β€’ Culpeper, VA

Immerse yourself in the breathtaking beauty of Culpeper County this fall, with route options tailored for every level of cyclistβ€”choose from 35, 65, or 100 miles to find the perfect fit for your endurance and experience.

🏷️ $50MetricCenturyGravel
⚑ Event Details & Specifications ›
Dataset Population2026 Verified Census
Qualified Distances
πŸ”οΈ Imperial Century (100 mi)
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… Oct 03, 2026
End Date2026-10-03T17:00:00
Starting VenueLenn Park
Street Address19206 Edwin Way
LocationCulpeper, VA 22701
GPS Coordinates38.48115, -78.00406 (Google Maps β†—)
OrganizerBlue Ridge Cyclery β†—
Entry Fee$50
RegistrationDirect Registration Link β†—
🏒 Hosted by: Blue Ridge CycleryπŸ“ 19206 Edwin Way, 22701

Mountains of Misery

May
πŸ”οΈ Imperial Century (100 mi)πŸ—ΊοΈ RWGPS Map (2)
πŸ“ Newport Start Hub β€’ Newport, VA

Notoriously punishing climbing challenge offering imperial century and double metric routes finishing atop Mountain Lake.

🏷️ $0cyclingbike ridedouble metriccentury
⚑ Event Details & Specifications ›
Dataset PopulationForward Calendar (Schedule Pending)
Qualified Distances
πŸ”οΈ Imperial Century (100 mi)πŸ—ΊοΈ RWGPS Map (2)
Event TypeCycling Century
Event StatusCancelled
Attendance ModeIn-Person (Offline)
DateMay
RWGPS TelemetryInteractive Route Map (2) → β€’ Send to Wahoo/Garmin β†— β€’ GPX ⬇ β€’ TCX ⬇
Starting VenueNewport Start Hub
LocationNewport, VA
GPS Coordinates37.306852, -80.50992 (Google Maps β†—)
OrganizerMountains of Misery Organizing Committee β†—
Entry Fee$0
RegistrationDirect Registration Link β†—
🏒 Hosted by: Mountains of Misery Organizing Committee

Rockbridge Gravel Grinder

πŸ“… Nov 01, 2026
⚑ Half Century (50 mi)
πŸ“ Raphine, VA

On Sunday November 1st at 10am ride the scenic back country roads of the Shenandoah Valley of Virginia. Three NEW routes of 54, 42 and 33 miles (63-75% unpaved) on the beautiful rolling hills of Augusta and Rockbridge Counties between Staunton and Lexington. There will be rest stops well stocked with food and drink in historic Brownsburg. Rides start and finish at the Rockbridge Vineyard and Brewery in Raphine...

🏷️ $70 - $80🚡 GravelHalf CenturyGravel
⚑ Event Details & Specifications ›
Dataset Population2026 Verified Census
Qualified Distances
⚑ Half Century (50 mi)
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… Nov 01, 2026
Street Address35 Hillview Rd
LocationRaphine, VA 24472
GPS Coordinates37.941694, -79.240944 (Google Maps β†—)
OrganizerBlue Ridge Events β†—
Entry Fee$70 - $80
RegistrationDirect Registration Link β†—
🏒 Hosted by: Blue Ridge EventsπŸ“ 35 Hillview Rd, 24472

Tour de Fall Line X - November 15th 2026

πŸ“… Nov 15, 2026
⚑ Half Century (50 mi)πŸ—ΊοΈ RWGPS Map (3)
πŸ“ Richmond, VA

Tour de Fall Line X - Sunday November 15, 2026 Event information subject to change. Sunday November 15th 7:00AM to 4:00 PM Ten years of Tour de Fall Line! - Join rvaMORE for a single track trail journey through the length of the James River’s fall line. Experience a tour of the trails of the James River Basin by mountain bike, hosted by rvaMORE to raise money for to support the Richmond region's trail network....

🏷️ $35 - $50Half CenturyRoadRWGPS Route
⚑ Event Details & Specifications ›
Dataset Population2026 Verified Census
Qualified Distances
⚑ Half Century (50 mi)πŸ—ΊοΈ RWGPS Map (3)
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… Nov 15, 2026
RWGPS TelemetryInteractive Route Map (3) → β€’ Send to Wahoo/Garmin β†— β€’ GPX ⬇ β€’ TCX ⬇
Street AddressCarrillon Shelter at Barker Field - 1300 Blanton Ave
LocationRichmond, VA 23221
GPS Coordinates37.539107, -77.482023 (Google Maps β†—)
OrganizerrvaMORE β†—
Entry Fee$35 - $50
RegistrationDirect Registration Link β†—
🏒 Hosted by: rvaMOREπŸ“ Carrillon Shelter at Barker Field - 1300 Blanton Ave, 23221

Tour de Madison

πŸ“… May 23, 2026
⏱️ Metric Century (62 mi)πŸ—ΊοΈ RWGPS Map
πŸ“ Hoover Ridge Park β€’ Madison, VA, VA

The Tour de Madison is an annual cycling event held in Madison, Virginia, benefiting the Madison County Parks and Recreation Authority. Riders of all ages and ability levels come together to celebrate cycling, creating an energetic, welcoming atmosphere throughout the community.

🏷️ $50Metric CenturyIntermediateFamily Ride
⚑ Event Details & Specifications ›
Dataset Population2026 Verified Census
Qualified Distances
⏱️ Metric Century (62 mi)πŸ—ΊοΈ RWGPS Map
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… May 23, 2026
RWGPS TelemetryInteractive Route Map (1) → β€’ Send to Wahoo/Garmin β†— β€’ GPX ⬇ β€’ TCX ⬇
End Date2026-05-23T14:00:00
Starting VenueHoover Ridge Park
Street AddressFairgrounds Road
LocationMadison, VA, VA 22727
GPS Coordinates38.384495, -78.296458 (Google Maps β†—)
OrganizerBlue Ridge Cyclery Events Promotions β†—
Entry Fee$50
RegistrationDirect Registration Link β†—
🏒 Hosted by: Blue Ridge Cyclery Events PromotionsπŸ“ Fairgrounds Road, 22727