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
7 Plotted Events43rd Ken Thompson Reston Century
📅 Aug 23, 2026 (6:30 AM – 5:00 PM)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.
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Event Type | Cycling Century (SportsEvent) |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Aug 23, 2026 (6:30 AM – 5:00 PM) |
| End Date | 2026-08-23T17:00:00 |
| Starting Venue | Reston Town Center West |
| Street Address | 1950 Opportunity Way |
| Location | Reston Town Center West, VA 20195 |
| GPS Coordinates | 38.96, -77.3456 (Google Maps ↗) |
| Organizer | Reston Bicycle Club ↗ |
| Organizer Contact | [email protected] |
| Entry Fee | $60.00, 75.00, 85.00, 95.00, 25.00 |
| Registration | Direct Registration Link ↗ |
Alpine Loop Gran Fondo
📅 Oct 06, 2024 at 8:00 AMA classic cycling event with a meaningful charitable connection, presented by the Cancer Journeys Foundation
⚡ Event Details & Specifications ›
| Dataset Population | Forward Calendar (Schedule Pending) |
| Event Type | Cycling Century (SportsEvent) |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Oct 06, 2024 at 8:00 AM |
| End Date | 2024-10-06T00:00:00 |
| Starting Venue | Downtown Harrisonburg |
| Street Address | Harrisonburg, VA 22801 |
| Location | Harrisonburg, VA 22801 |
| GPS Coordinates | 38.448864, -78.871438 (Google Maps ↗) |
| Organizer | Bishop Racing LLC ↗ |
| Entry Fee | $0 |
| Registration | Direct Registration Link ↗ |
Cap2Cap
📅 May 08 – 09, 2026The 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.
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Event Type | Cycling Century (SportsEvent) |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 May 08 – 09, 2026 |
| End Date | 2026-05-09T00:00:00 |
| Starting Venue | Chickahominy Riverfront Park and Dorey Park |
| Location | Virginia Capital Trail, VA |
| GPS Coordinates | 37.5594, -77.4472 (Google Maps ↗) |
| Organizer | Virginia Capital Trail Foundation ↗ |
| Organizer Contact | [email protected] |
| Entry Fee | $0 |
| Registration | Direct Registration Link ↗ |
Culpeper Cycling Century
📅 Oct 03, 2026Culpeper Cycling Century
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Event Type | Cycling Century (SportsEvent) |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Oct 03, 2026 |
| Starting Venue | Lenn Park |
| Location | Lenn Park, VA |
| GPS Coordinates | 37.431573, -78.656894 (Google Maps ↗) |
| Organizer | Cycling Virginia ↗ |
| Entry Fee | $0 |
| Registration | Direct Registration Link ↗ |
Culpeper Cycling Century and Tour
📅 Oct 03, 2026Immerse yourself in the breathtaking beauty of Culpeper County this fall, with route options tailored for every level of cyclist—choose from 35, 65, or 100 miles to find the perfect fit for your endurance and experience.
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Event Type | Cycling Century (SportsEvent) |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Oct 03, 2026 |
| End Date | 2026-10-03T17:00:00 |
| Starting Venue | Lenn Park |
| Street Address | 19206 Edwin Way |
| Location | Culpeper, VA 22701 |
| GPS Coordinates | 38.48115, -78.00406 (Google Maps ↗) |
| Organizer | Blue Ridge Cyclery ↗ |
| Entry Fee | $50 |
| Registration | Direct Registration Link ↗ |
Mountains of Misery
MayNotoriously punishing climbing challenge offering imperial century and double metric routes finishing atop Mountain Lake.
⚡ Event Details & Specifications ›
| Dataset Population | Forward Calendar (Schedule Pending) |
| Event Type | Cycling Century (SportsEvent) |
| Event Status | Cancelled |
| Attendance Mode | In-Person (Offline) |
| Date | May |
| Starting Venue | Newport Start Hub |
| Location | Newport, VA |
| GPS Coordinates | 37.306852, -80.50992 (Google Maps ↗) |
| Organizer | Mountains of Misery Organizing Committee ↗ |
| Entry Fee | $0 |
| Registration | Direct Registration Link ↗ |
Tour de Madison
📅 May 23, 2026The 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.
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Event Type | Cycling Century (SportsEvent) |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 May 23, 2026 |
| End Date | 2026-05-23T14:00:00 |
| Starting Venue | Hoover Ridge Park |
| Street Address | Fairgrounds Road |
| Location | Madison, VA, VA 22727 |
| GPS Coordinates | 38.384495, -78.296458 (Google Maps ↗) |
| Organizer | Blue Ridge Cyclery Events Promotions ↗ |
| Entry Fee | $50 |
| Registration | Direct Registration Link ↗ |