The 10 Best Cycling Events in Virginia!

Virginia’s terrain ranges from the sea level beaches to the hilly Appalachians. Whether you’re a beginner or a seasoned cyclist, the following races offer something for everyone. One doesn’t have to look too hard to find a race any time of year in Virginia. Below are 10 of the best in the state. 

2. Cranksrising Scavenger Hunt Charity Ride and Race, Richmond, VA

The Cranksrising bicycle race is a Scavenger Hunt “to benefit the Safe Harbor Shelter and to bring awareness of One Billion Rising.” Essentially, participants get a list of local stores and see how many items they can carry and bring back to the finish line. The fastest riders get prizes. All prizes are donated to survivors of sexual and domestic abuse. Make sure to sign up ahead of time!

2. Spring Thaw Trail Run and MTB Trail Series

The Spring Thaw is a series of cycling races held over three weekends to celebrate the changing of the season. The race has events for trail runners and mountain bikers. Check the website for entry fees and prize information. 

3. Shenanduro, Bentonville, VA

Organized by Rev3, the same folks behind the Spring Thaw Trail Run, the Shenanduro multi-sport weekend offers the opportunity to run, ride, and paddle “through some of the best trails and waterways in Virginia.” The race offers a 10K, a six or nine-hour mountain bike course, as well as two different paddle distances on the Shenandoah River. Prizes are awarded to the top three winners in each division. 

4. Tour de Chesapeake, Mathews, VA

The annual Tour de Chesapeake is characterized as a “casual, flat, laid back, fun, and easy” cycling event. From the website, the race is described as having “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!” The Tour de Chesapeake is a wonderful way to experience the natural beauty of the Chesapeake Bay and welcome in the spring season. 

5. Cranky Monkey MTB Race Series, Quantico, VA

The Cranky Monkey MTB race series is put on by the Singletrack Cycling Open Registration Events, or SCORE, non-profit. The goal of SCORE is to create a “unique race experience where mountain bikers can enjoy the sport of racing while giving back to the trails.” The Cranky Money combines traditional endurance and cross country series with a cross-country night race. Riders compete in teams with many different classes and divisions. 

6. Jamestown Gran Fondo, Williamsburg, VA

The Jamestown Gran Fondo takes place in Virginia’s Historic Triangle. The trail is on low traffic roads with smooth pavement and few hills. At the end of the race, participants are invited to a barbeque and beer at the historic Jamestown Settlement. 

7. Culpeper Gran Fondo, Culpeper, VA

The Culpeper Gran Fondo is a relatively new race, having only started in 2015, but has so far gotten wonderful reviews. The Culpeper Gran Fondo offers a 32, 62, and 100-mile option, each starting at 7:30 a.m. The rides aren’t flat, but the scenery is well worth the extra work. 

8. Jefferson Cup, Charlottesville, VA

The Jefferson Cup Road Race is an annual race in Charlottesville, Virginia. Ride through beautiful and historic Charlottesville on either the last Sunday in March or the first Sunday in April. Make sure to check out their Facebook page for frequent updates and more information.

9. Ephesus Junior Academy IRide Scholarship Program, Midlothian, VA

The Ephesus Junior Academy IRide Scholarship Program is a newcomer on the cycling scene in Virginia. The event includes an 18-mile charity bicycle ride as well as a 5K-charity fun run. All funds go to helping the scholarship program. 

10. The Trail Mix, Aldie, VA

The Trail Mix in Aldie, Virginia offers a 5K, 10K, or half marathon. Solo-bikers and teams are welcome to compete for prizes based on whoever gets the most laps. Participants are invited to hang out for the entire weekend to enjoy a campout. The trails are suitable for beginners as well as experts.  

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