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Fall Bike Rides from Waynesboro, VA

September 17, 2019
Stories, Outdoors, Food, Craft Beverage

Helmet…check. Spare tubes…check. Sense of adventure…check.
If you’re looking for a bicycling destination that offers a variety of picturesque landscapes and delectable wayside stops, pack your gear and head to the Shenandoah Valley. With Waynesboro, Virginia, as your base camp, you’ll have an abundance of on-road and off-road routes to choose from, taking you everywhere from the peaks of the Blue Ridge Mountains to the historic towns nestled below. Start your adventure rested and well-fed with a night at Heritage Hill B&B or the bike-friendly Iris Inn, then spend your day exploring one of these suggestions.

Sample the Fruits (and Grains) of the Valley

(Photo: Flying Fox Vineyard)

This Waynesboro to Nellysford loop will bring you past some of our region’s delicious offerings. You’ll find stunning views and wines at Veritas Vineyard and Winery, internationally acclaimed craft spirits at Silverback Distillery, and cold taps at Wild Wolf Brewing Company.   Wild Wolf’s farm-to-fork restaurant makes this the perfect rest stop on your tour. Refreshed, pedal south to Flying Fox Vineyard to sample one of their Virginia Vermouths or premium wines. And no Nellysford loop would be complete without a stop at Bold Rock Hard Cider! For an abundance of additional grain, grape, berry, and fruit adult beverage options on your route, be sure to check out this map.

Ramp Up for Big Fun

Up for a big challenge? Check out the Big Levels / Sherando mountain biking trail system! Recommended by the outdoor pros at Rockfish Gap Outfitters, the Sherando Lake Recreation Area in George Washington and Jefferson National Forests offers mountain bikers 20 miles of singletrack trails and dirt/paved roads. Reward your efforts by taking the fireroad over to the Blue Ridge Parkway and sailing down six miles of “America’s Favorite Drive (Ride).” You also have the option of connecting up with U.S. Bicycle Route 76.

Stop to Taste the Local Flavor


For a scenic ride along some of our county’s flattest road miles, Bike the Valley recommends this 35-mile Waynesboro to Grottoes loop. Be sure to build in time for a tour through Grand Caverns, a National Natural Landmark, or the more rugged Fountain Cave Adventure Tour. When you return to Waynesboro, cap off your ride with a meal at the Green Leaf Grill, whose healthy Mediterranean- and Cajun-inspired cuisine will fuel your next adventure.


For additional route suggestions and local resources or to brush up on Virginia’s bicycle laws, visit Bike the Valley. When it comes to autumn bike rides, you have a lot of choices–better make it a long weekend in Waynesboro!