Two-Wheeled Touring Near Waynesboro – Bicycle and Motorcycle Itineraries

Sometimes the ride is as exhilarating and beautiful as any destination. If you’re looking for sweeping turns, windswept mountain vistas, or country roads to cruise, these bicycle and motorcycle itineraries are sure to inspire.

Pedaling on Pavement

Day Trip Tours from Waynesboro are plentiful. Beginners and family-friendly options include the South River Greenway, stretching from Constitution Park and meandering along the South River, which on Saturday mornings features the Waynesboro Farmers Market. Or stretch a little further with the 12.5 mile Waynesboro-to-Dooms Day Loop, which takes you along the South River as it flows north towards its confluence with the North River. Intermediate riders may love the Waynesboro-to-Grottoes Loop which, over the course of 35 miles, can include a tour of Grand Caverns in the town of Grottoes and passes the renowned horticulturalist André Viette’s extensive perennial garden and nursery on Long Meadow Road.  Don’t be shy about exploring other options, as Bike the Valley’s database of On Road rides remains extensive.

For the most adventurous, Overnight Bicycle Tours are right at home here, as the famous TransAmerica Bicycle Route passes along the Blue Ridge Parkway. Or for those new to Bike Camping, join the Shenandoah Valley Bicycle Coalition for a one-night adventure in April.

Free and inviting Group Rides occur in the Valley every week, so be sure to check out the Bicycle Coalition’s Ride Calendar if you’d like to tour with locals who know the best climbs and descents. Organized cycling events occur throughout the year, ranging from a Farm to Fork Fondo to the annual Shenandoah Valley Century and the Fall Foliage Bike Festival.

Mountain Biking Adventures

If your comfort with dirt leans towards the flat and the wide, Waynesboro is the perfect central location for exploring a statewide collection of Rails to Trail rides — turning old railroad beds into bicycle powered tours of trestles, river beds, and tunnels. For more topography, plenty of dirt, but still wide and less technical riding, in 2018 the Trans Virginia Bike Trail launched, with 500+ miles of unpaved country and forest roads, double track and rail trails.

For riders seeking single track trails and mountain topography, both the Blue Ridge and the Appalachian Mountains invite. Nearby Montgomery Hall Park, Hillandale Park, and Mint Springs Valley Park offer dense, developed trails accessible to all skill sets. Longer adventures await along the recently upgraded Narrowback Mountain Loop and the Sherando Lake Advanced Loop. The Massanutten Bike Park opens for the summer season in April, providing lifts to the top of the mountain, allowing riders to experience the thrill of downhill mountain biking — all without the work of the climb!

Motorcycling Routes

From Valley hills to Skyline drives, Waynesboro offers the best in lowland to mountain top touring. Recommended motorcycle itineraries include a 160+ mile Shenandoah Valley tour and a Valley to Sky loop of over 200 miles. Also be sure to check out motorcycle tours along the Blue Ridge Parkway, Shenandoah National Park, and Crabtree Falls.

For those new to riding along windy ridges, be sure to check out Blue Ridge Motorcycling’s guide to Riding Safely in the Mountains. Their site also includes insider tips on motorcycle destinations, such as the local Iris Inn Bed and Breakfast, offering all the amenities from a Bike Wash Station to mountain views to an end-of-ride Jacuzzi.

The Iris Inn Bed and Breakfast offers a glorious ending to a long day of riding.