Virginia Century Bike Ride Database
GroundForce IT Snowflake Ride Sunday March 11th 18, 34 or 42.5 miles
This is an annual event starting in Richmond’s Scotts Addition to benefit the Richmond Cycling Corps program to help empower youth living in public housing to break the cycle of poverty by building confidence and work ethics.
TAP IT Saturday March 24th 30 miles
This is an escorted ride through the back roads of Chesapeake, all proceeds go to benefit fallen Law Enforcement Officers and their survivors. This is a slow and easy ride to give everyone an opportunity to socialize and learn about this great cause.
Spring Metric Century Saturday April 21st 62 miles
Cycle through the Shenandoah Valley, recognized as one of the most beautiful regions in America. This spring cycling event helps to prepare avid riders for the more difficult 100 mile event organized by Bike Shenandoah in the fall. Proceeds from this event benefit six service agencies that cater to the local community.
Powhattan Historic Bike Tour Sunday April 29th 31, 62 or 100 miles
Annual Powhatan Historic Bike Tour to benefit the Free Clinic of Powhatan. The tour has three (3) routes designed to appeal to cyclists of all abilities. All the bike routes are on gently rolling country roads with scenic views. There are also fully stocked rest stops at unique historic sites along your way to the finish.
Hampton Roads Tour de Cure Saturday April 28th 10, 25, 65 or 100 miles
The Tour de Cure is more than just a cycling event it’s a day packed with excitement and energy where riders of all levels join forces in the fight to Stop Diabetes® and raise critical funds for diabetes research, education and advocacy in support of the American Diabetes Association. Requires a registration fee plus a minimum fundraising amount of $200.
Devils Backbone Blue Ridge Metric Sunday April 14th 45 or 63 miles Ride a very beautiful and challenging metric century in the Blue Ridge Mountains of Nelson County VA. The ride will ascend the epic climb of Vesuvius and descend beautiful Crabtree Falls Highway and will start and finish at Devils Backbone Brewing Company. Your registration includes gift card for beer or food at Devils Backbone Brewing Company and free primitive camping site at Devils Backbone Brewing Company. Crossroads of Route 151 and Route 664.
Pedal Through Petals Sunday April 29th Leisure Ride
This is a guided tour of Richmond's beautiful architecture and gardens, on your bike! There are several stops along the way in historic places and beautiful gardens. Proceeds benefit the Massey Cancer Center which works to make important discoveries about cancer, and to translate those discoveries into better cancer prevention, detection, treatment and control of cancer. Starts and finishes at the Lakeside Farmer’s Market.
Operation Bike for the Brave Saturday May 5th 13, 25, or 50 miles
(Formally Ride for Rise and Conquer) This ride benefits McGuire Veterans Hospital and helps to support the Adaptive Sports Program for wounded vets – 100% of all donations and ride entry fees will go to local veterans. The ride starts from Winns Baptist Church in Glen Allen, Virginia.
Pedal the Parkway Williamsburg Saturday May 5th 8 miles
GREAT FAMILY RIDE; Cycle, run or hike along the Colonial Parkway by the shores of the scenic James River from Jamestown to Williamsburg or vice versa and it’s totally FREE, but bike helmets and registration is required. Eight miles of empty, car free pavement will be waiting for you and your family to have fun in the great outdoors. This is a great ride to introduce younger family members to the joys of road cycling. Start at your own time between 8 am and 1 pm, proceed at your own pace and enjoy refreshments at the midway point. While in Williamsburg, also consider riding the Virginia Capital Trail.
Cap2Cap Saturday May 12th 25, 50, or 100 miles
Richmond to Williamsburg and Williamsburg to Richmond and back. Take in the abundant beauty as the route brings you through Revolutionary and Civil War battlefields and across farmland that remains largely unchanged since our country’s colonial days. When available along your chosen route, please hop on the beautiful Virginia Capital Trail and enjoy a safe spin on this world-class amenity!
Tour de Madison Saturday May 19th 20, 45 or 65 miles
Ride through the rolling hills and country side of historic Madison County. Since 1988, road cyclists in Madison and the surrounding counties have gathered in May for a tour of Madison County. This is a fully supported event sponsored by the Madison County Parks and Recreation Authority.
Tour de Chesapeake Saturday May 19th 22, 24, 25, 30, or 101 miles
The County of Mathews, the Mathews Land Conservancy, and the Mathews Visitor Center are your hosts for this event. Celebrate the arrival of spring with a weekend of scenic cycling – great FLAT routes with views of the water everywhere you turn delicious local eats, toe-tapping music, and nice, down-home folks to help you with whatever you need.
Tour de Floyd Saturday May 19th 62 miles
The Tour de Floyd is a scenic metric century ride with nearly half of its 62 miles along the Blue Ridge Parkway. Come experience Floyd- the place with only one stoplight in the entire county, no four lane highways and more cows than people. Enjoy the 50 mile views from Blue Ridge Parkway overlooks and farm laden country roads – paved of course. Proceeds benefit Floyd Rescue Squad.
Farm to Fork Fondo Shenandoah Multi Day May 19th - 20th 10 to 100 miles Belle Grove Plantation in Middletown will serve as the start-finish venue on May 20, and host a pre-ride ‘Meet the Farmers Dinner’ on May 19. The event will include gourmet aid stations at several farms in the Shenandoah Valley region, where cyclists will sample chef-prepared food made from each farm’s ingredients.
Storming Thunder Ridge Sunday May 20th 27, 45, 75 or 100 miles
Storming Thunder Ridge starts in Lynchburg and is a fund-raiser benefiting the YMCA of Central Virginia. This is a challenging ride in the Blue Ridge Mountains with a 12.6 mile climb of Thunder Ridge and several smaller climbs up to 9,000+ ft. of climbing. Lots of food afterwards. Riders can use the YMCA amenities which include shower facilities, whirlpool, and swimming pool after the ride. Bring your own a towel and swimsuit. 6 MAY Event Day Date Options General Description
Pedal for the Pig Saturday May 26th 32, 50 or 64 miles
Join the Peninsula Bicycling Association on its annual Spring ride (formally The Smithfield Challenge) starting from Windsor Castle Park in Smithfield, VA. The park is near downtown Smithfield at 301 Jericho Rd. Rides take place on quiet and lightly traveled roads though Isle of Wight County. After the ride stay for BBQ at Windsor Castle Park.
Wilderness Road Ride Saturday May 26th 29, 58 or 79 miles
A scenic and historical adventure through southwest Virginia’s beautiful New River Valley, the ride follows part of Daniel Boone’s Wilderness Road. This is a ride for the whole family to enjoy, with something for everyone -four (4) routes to choose from. All routes start and finish in Radford, at the Dedmon Center and Bisset Park. This is a must ride for cyclists of all ages and athletic abilities.
Mountains of Misery Sunday May 27th 100 or 124 miles
Mountains of Misery is a challenging bike ride for dedicated road cyclists through the heart of southwest Virginia. The annual timed event features century (100+ mi) and double-metric century (200 km/124+ mi) options—both ending in a tough, four-mile 12%–16% graded climb to the finish. Join the post-ride celebration, including lots of food with plenty of time to relax and enjoy your accomplishments with all your cycling friends.
Triple Peak Gran Fondo Saturday June 2nd 57, 71 or 115 miles
Element Adventures is proud to announce the first Triple Peak Fondo, featuring three iconic climbs in the greater Winchester area! The Triple Peak Century+ route has it all: plenty of miles, beautiful pastoral vistas, stiff mountain climbs (with accompanying descents!), and even a couple miles of gravel. A portion of each participant’s entry fee will be donated to Congregational Community Action Project (CCAP), a local charity. They ask that all participants bring a canned food item to donate to the food pantry.
Bike MS Colonial Crossroads Multi Day June 2nd - 3rd 40, 60, 75 or 100 miles each day
There are three (3) different starting points and multiple options – Richmond to Williamsburg and back - 25 or 50 mile rides Sun, 75 or 100 mile rides Sat & Sun. Smithfield to Williamsburg and back (40, 75, or 100 mile rides either days, or 60 miles on Sunday), and Williamsburg the first day, concluding at Colonial Williamsburg with the Smithfield and Richmond routes coming together. Enjoy a scrumptious feast, massages, musical entertainment and an evening program. Day two begins with a hearty breakfast before cyclists head back to Smithfield/Richmond and their respective finish line.
Annual World Hunger Bike Ride Saturday June 9th 5, 10, 25, or 50 miles
The longest running continuously held cycling event in Franklin County. Bring the whole family for a leisurely ride along the scenic country roads of Franklin County. Cyclists of all skill levels are welcome! Departs from Antioch Church of the Brethren in Rocky Mount. Rest stops and SAG support are provided.
Lee Warren Queen City Century Saturday June 14th 25, 50 or 100 miles
The Lee Warren Queen City Century Bike Tour, a ride through the beautiful scenic Shenandoah Valley. The route will take riders west of Staunton, out into the countryside of Augusta County. The ride provides scenic vistas, county farms, small towns, and quiet rural roads. Proceeds benefit Renewing Homes of Greater Augusta that provides critical home repairs and modifications for elderly, disabled, and disadvantaged homeowners of Staunton, Waynesboro, and Augusta County.
Air Force Association Cycling Classic Challenge Ride Sunday June 10th 15km/9 miles
Circuit The Challenge Ride is an amateur, non-competitive, participatory ride held in Arlington, VA and open to cyclists of all abilities. All participants will start and end in Crystal City. The ride will be held on a closed, 15km/9mile circuit in and around the Pentagon, Crystal City and the Air Force Memorial. Participants have up to 3 hours to complete as many laps as possible. Anyone 10 and over can ride, under 18 must have parent or guardian sign their waiver. Your registration fees include timing support, a bib number, finishing medal and an event t-shirt.
Big Pencil to Big Walker Charity Ride Saturday June 16th 32, 44 or 62 miles
The Big Pencil to Big Walker Charity Ride - Proceeds benefit HOPE, an umbrella human services organization delivering housing and anti-poverty programs to the southwest Virginia counties of Wythe, Bland, Carroll, Smyth and Grayson and the City of Galax. The ride begins near downtown Wytheville and the iconic Wytheville Office Supply "Big Pencil" before heading out through the pastoral counties of Wythe and Bland. There is a KOM timed ascent of the first climb of Big Walker, with several prizes awarded. The ride coincides with the opening day of the annual Chautauqua Festival in the Park, an eight day family oriented arts and music festival.
Le Tour de Shore Saturday June 16th 17, 30, 55 or 70 miles
Come bike on the beautiful country roads of the Eastern Shore. Its charming towns are sprinkled with historic homes, museums, art galleries and shops that you will want to come back and visit after your ride. This is a fully supported ride hosted by the Eastern Shore of Virginia Chamber of Commerce.
Bike Virginia Tour Multi Day June 22nd thru 27th Varies Each Day 10 to 101 miles Ride the River Tour – Bike Virginia’s annual event with a pilgrimage to one of Virginia’s most prized cycling areas—The focus is on great riding, relaxing, entertainment, exploration, fun and just the right services to keep you happy and comfortable. Come for a day, three days (weekend or weekday), or the whole 6-day adventure!
Element Adventures Vineyard Tour Sunday July 8th 30 miles
Casual ride through the countryside around Winchester, with a catered lunch and wine tasting at Valerie Hill Vineyard and Winery. Ride as a group at about a 12-14 mph pace. The ride is on paved roads, with 20 miles to get to the winery and 10 miles to return to the finish. This ride is guided and there will be a SAG wagon and mechanic on hand. If you decide to purchase any wine at the Winery, they will be transported back to the finish. Note – space is limited, register early.
Gran Fondo Alleghany Saturday July 21st 29, 63, or 99 miles
Come to scenic Covington and Clifton Forge in the Alleghany Highlands region of Virginia for this annual event. Easily accessible from Interstate 64. The Alleghany Highlands' majestic peaks and picturesque valleys might be mistaken for a region of France or Germany. With electronic chip timing, a King of the Mountains competition, and a mass start, all the elements of the classic European Gran Fondo will be there, served up with southern hospitality.
Culpeper Gran Fondo Saturday August 4th 32, 62 or 100 miles
The Culpeper Gran Fondo began in 2015 with rave reviews. Join fellow cyclists on low traffic, country roads that wind through horse country, farmland, forests, trout streams and vineyards all within sight of the Blue Ridge Mountains. None of these rides are flat, this is central Virginia, but these rides are gorgeous and fun. Each distance is fully supported with mechanics and well stocked aid stations.
Tour de Scholar Charity Bike Ride Saturday August 4th 5, 25, 35 or 60 miles
The Martinsville-Henry County Chamber of Commerce’s Education Foundation presents the Annual "Tour de Scholar" charity bike ride. All proceeds benefit local teachers, students and schools. The ride will start and finish at the Smith River Sports Complex. All routes will be marked and supported with sag and rest stops. Meal provided at the conclusion of the ride. Participants will be eligible for great door prizes.
Mountain Mama Road Bike Challenge Saturday August 4th 27, 53, 67 or 105 miles
This is one of the most beautiful and challenging road events in Virginia. This Highland County annual event features 4 courses of different ability levels and covers 2 States, 3 Counties, 9 mountains and 10,000 feet of climbing. Treat yourself to a warm southern welcome and ride through some of the less traveled roads in rural Virginia. Registration begins in February.
Burke’s Garden Century Saturday August 18th 62 or 102 miles
Burkes Garden, often called “God’s Thumbprint”, is Virginia’s largest rural National Historic District just seven miles from the nearby Town of Tazewell. A deep bowl shape, it is the highest valley in Virginia at over 3,000 feet, and is surrounded by a single mountain ridge with only one paved entrance. This ride has been a tradition for the New River Valley Bicycle Association since 1997, which has rapidly gained popularity as a fast, easy century for anyone who loves to ride bicycles. Many novice cyclists enjoy this century as their first, while advanced riders test their hammering ability to plug out a 100 miles at a fast pace.
Reston Annual Century Ride Sunday August 26th 35, 65 or 103 miles
The annual ride is limited to 1,500 riders. The Reston Bicycle Club will host a post ride party at the Reston Town Center Pavilion from 12:30 pm to 5:00 pm (with food service until 4:30 pm) for no additional cost for participating cyclists. Friends and family can attend for $15 per person. The event proceeds benefit various local support and non-profit organizations.
Tour De Valley Saturday September 1st 62 or 100 miles
The Tour de Valley takes you on a scenic tour of the Shenandoah Valley and includes a t-shirt, stocked aid stations, and SAG vehicle support. You are welcome to stay for an after party at the War Memorial Pool at Ridgeview Park where participants can take a swim and enjoy pizza, subs, and beverages! Put on by the City of Waynesboro Parks and Recreation.
Shenandoah Valley Century Sunday September 9th 25, 50 or 100 miles
A valley tradition with scenic vistas, small towns, beautiful farms, quiet roads, and more. All routes are paved and have low traffic volume. Ride at your own pace, the route will be patrolled by automobile sag to provide assistance as needed. A food and drink stop is provided every 25 miles and at the midpoint of the 25-mile ride. The ride starts in Harrisonburg, VA and is sponsored by the Shenandoah Valley Bicycle Coalition.
Surry Century Saturday September 8th 25, 50, 75, or 100 miles Experience the heart of Southeastern Virginia by bike and see rural towns, farmland, historic plantations, and very few cars – roads are flat and slightly rolling. The ride starts from the Surry Athletic Field behind the Surry County Offices at 45 School Street, Surry, VA.
Heart of Virginia Bike Festival Saturday September 15th 11, 34, 65 or 101 miles Heart of Virginia Bike Festival is the Richmond Area Bicycling Association’s annual cycling event. The ride starts and finishes at the Hanover County Government Complex on US Route 301 just south of the intersection of Routes 54 and 301. A fully supported ride on beautiful rural roads with farms and rolling hills. Afterwards stay for a great meal. Proceeds benefit the Brain Injury Association of Virginia and Bike for Kids.
Rappahannock Rough Ride Saturday September 15th 12 or 63 miles
Take a ride through the hills of Rappahannock County in this popular bicycle event. Multiple route options range from a family friendly 12 mile loop through the Town of Washington and Flint Hill, two paved/unpaved road “Rough Ride” options to the full 63 mile paved route. Proceeds benefit the Fauquier Free Clinic.
Climb to Conquer Cancer Saturday September 22nd 26, 44, or 63 miles (Video) A short urban warm-up and then two competitive (timed) climbs of Richmond’s Libby Hill and a scenic ride through the countryside. Age group awards for KOM/QOM – food and fun afterwards at Stone Brewery.
Cannon Ball Century Sunday September 30th 30, 67 or 102 miles
Enjoy the beautiful country side of Stafford County near historic Fredericksburg Virginia Secluded woodland roads, agricultural fields and horse farms in the midst of historic locations from the colonial era and the civil war form the backdrop. Includes great rest stops, post-ride lunch at Curtis Park with music.
Jeremiah Bishop’s Alpine Loop Gran Fondo Sunday September 30th 36, 62, 78, 100 or 107 miles
The route begins in Harrisonburg, Virginia and covers approximately 107 miles, featuring over 11,000 feet of climbing. While the Alpine Loop is a challenge, it’s an adventure suitable for VERY fit cycling enthusiasts. You don’t need to be a racer to tackle these mountains! In fact, well prepared riders who set a brisk steady pace and take full advantage of the rest station amenities are sure to reach the finish line. There are two timed KOM/QOM sections.
Culpeper Cycling Century Sunday October 6th 35, 65 or 100 miles
Located in Culpeper, ride scenic roads past historic landmarks, rolling hills and sparkling rivers, lakes and streams. This ride benefits the Culpeper Recreation Foundation, Inc. (a 501(c) 3 non-profit) as they strive to achieve their mission of promoting recreation in Culpeper County. Registration begins February 1st .
Tour de Bland Saturday October 6th 15, 37, 73 or 100 miles
The Tour de Bland is an annual road cycling ride and 5k run to support the fundraising efforts for the Relay For Life in Bland County, VA. The entire event is hosted by employees and friends of ABB's Dry-type Transformer factory located just a few blocks from the starting line. Ride through beautiful fall county roads and depending on your route, make the climb up and over 4 mountains.
Tour de Greene Saturday October 13th 40, 62 or 100 miles
The Tour de Greene ride benefits the Greene County Habitat for Humanity. Event starts in Ruckersville, VA which is north of Charlottesville. This is a fully supported ride and you are invited to stay and enjoy food and fun afterwards.
Tour de Midnight Saturday October 13th 35 or 65 miles
Tour de Midnight is a bike ride supporting the Epilepsy Foundation of Virginia and originates from Midnight Brewery in Rockville, VA which is located just west of Richmond on I-64 in Central Virginia. Come and see the beauty of the fall foliage and ride as your journey will have you traversing through the farmlands of Rockville, historic Town of Montpelier, while some of you will have breathe taking views of Woodson’s Mill, Lake Anna and a crossing of the South Anna River. Afterwards, everyone is invited to enjoy the hospitality of Midnight Brewery.