Tucked between the Allegheny and Blue Ridge mountains in the northern half of Virginia’s Shenandoah Valley, Shenandoah County is a pastoral patchwork of horse-roved meadows, blooming orchards, meticulously manicured vineyards, Civil War battle sites, and amiable towns. The collection of designated scenic byways and picturesque roads meandering through the county make the area a world-class destination for road cyclists. Riders have almost infinite options for cobbling together the ideal circuit. Choose a winery-studded loop, circuits showcasing the county’s history, or multi-day excursions stringing together some of the Shenandoah Valley’s most photogenic areas.

Epic Road Routes


Enjoy a variety of routes ranging from winery tours to multi-day excursions.

Maggie Deegan

Howard Beizer of the Peninsula Bicycling Association, based in Newport News, recommends two circuits in Shenandoah County. The first ride is a 30-mile trip through the southern portion of the county, between New Market and Mount Jackson. The trip includes the option to detour to attractions like the subterranean Shenandoah Caverns, home to the famed geological bacon formations, or Meems Bottom Bridge, one of just seven covered bridges in Virginia.

The second cycling trip is a 40-mile figure-eight between Woodstock and Mount Jackson. The route includes a stretch along the Shenandoah River and plenty of pleasant pit stops, like a wine tasting at Shenandoah Vineyards or a detour to the Swover Creek Farm Brewery for seasonal microbrews and wood-fired pizza.

Riders can also opt for the ultimate 47.7-mile loop around Shenandoah County, which includes a roll through one of the region’s highlights–Fort Valley. A quilted mosaic of farms and fields nestled between two flanks of Massanutten Mountain, Fort Valley is dubbed the ‘valley within the valley,’ and makes for a stunning backdrop. Beginning in Strasburg, the half-century circuit also includes a ride through the Elizabeth Furnace area of the George Washington National Forest, and past the towns of Edinburg, Woodstock, Toms Brook, and Mauretown.


Take a tour through small, idyllic towns like Edinburgh.

Rod Shepherd/Shenandoah County Tourism

For history buffs, one of the highlights of riding in Shenandoah County is the chance to cycle historic Route 11, which runs the length of the county, from Strasburg to Mount Jackson. Also referred to as the Old Valley Pike, Route 11 began as a hunting ground and migration route for regional Native American tribes. It later functioned as a 19th century toll road, and during the Civil War, served as a vital transportation artery for General Thomas ‘Stonewall’ Jackson’s whirlwind 1862 campaign through the Shenandoah Valley. Today, the roadway is one the county’s premier recreational thoroughfares, and a ride on Route 11 can easily be tacked onto any regional cycling outing.

Rolling Tours


Scenery along Shenandoah County rides is not only beautiful but historical as well.

Malee Oot

Besides the smorgasbord of scenic rides, cyclists headed to Shenandoah County also have several options for guided tours, including everything from multi-night excursions to single day rides. Shenandoah Mountain Touring in Harrisonburg specializes in trips to the Shenandoah Valley, organizing both mountain biking expeditions in the George Washington National Forest and regional road rides. The outfitter can also arrange tailor-made tours, including routes showcasing some of the Shenandoah Valley’s most enticing swimming holes, for groups or solo riders of all skill levels.

North Carolina-based operator Carolina Tailwinds offers a five-night, inn-to-inn tour of the northern portion of the Shenandoah Valley. The cycling trip includes a pedal through Shenandoah County stringing together highlights like Massanutten Mountain and historical Strasburg, plus other regional gems, like Skyline Drive in Shenandoah National Park. Located in Colorado, Lizard Head Cycling Guides also offers a lengthy ramble through the Shenandoah Valley. The four day expedition hopscotches between inns, and bed and breakfasts, ultimately wrapping up in Shenandoah County at Cave Ridge Vineyards, just outside Mount Jackson.

Cyclers seeking the tranquil solitude of a solo ride–and a more budget-friendly touring option–can opt for a self-guided expedition choreographed by Virginia Bicycling Adventures. Offering trips as short as a weekend or as long as a week, the Strasburg-based outfitter arranges self-guided tours in the northern portion of the Shenandoah Valley, arranging all the nitty-gritty details from overnight accommodation to meals at local eateries, so riders just have to worry about soaking up all the scenery.

Originally written by RootsRated Media for Shenandoah County.Featured image provided by Diane Gardner/Shenandoah County