The 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 the best in the state. 

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. 

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. 

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. 

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. 

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