Bicycling in the Shenandoah Valley

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Stokesville Lodge Bicycling. Scott K. Brown Photography courtesy Virginia Tourism Corporation.

The Shenandoah Valley is a special part of western Virginia and the easternmost panhandle of West Virginia. The diverse terrain makes it attractive for both mountain and road cycling. The Blue Ridge and Allegheny Mountains rise to the east and west, respectively, cradling a fertile, bucolic stretch of land approximately 150 miles long and averaging 30 miles wide. Massanutten Mountain rises in the middle of the Valley, bisecting a 50-mile stretch and creating more higher altitude adventures.

When you choose to bike the Shenandoah Valley, you’re presented with many possibilities. Start here and dig deeper for plethora more.

Road Cycling


Don’t be deterred by the name. The Waynesboro Dooms Day Loop is an easy 12.4 miles without a lot of elevation change. Start and end in downtown Waynesboro, taking in the views of South River and Blue Ridge Mountains as you go.

The Middlebrook M&M route is a short 13 miles, slow and steady on less-traveled backroads in Augusta County, Virginia. Expect to see farms while you pedal through shady lanes and fields.


The Port Republic Route begins just outside Massanutten Resort and takes you on a 38.1-mile low-traffic excursion featuring multiple hills and elevation gain of 1,725 feet. Don’t worry; what goes up must come down as well.


Cross the Virginia/West Virginia state line with the Highland County Mountain Mama 50 Mile Loop. Steep grades in and out of the Monterey start/finish point are shady, thankfully, and there are stopping points along the way. Elevation change is 4,324 feet on this one.

Your legs will burn when you tackle the Blue Ridge Parkway North route from Buena Vista to Vesuvius. Route 60 to the Blue Ridge Parkway entrance is steep and winding, and the descent from the Parkway to Vesuvius is much the same. Make it a full loop for 45.2 miles, incorporating an easy downhill coast along South River.

Gravel Rambles

The Harrisonburg Dayton Gravel Grinder begins in downtown Harrisonburg but you’ll wind up feeling a world (and maybe a lifetime) away as you make your way past Old Order Mennonite farms complete with horse-and-buggy transportation. The route is 36.4 miles but lacks a lot of climbing. Stroll on and reward your sooty spin with a frothy beverage at the end.

Not that you’ll want to tackle the TransVirginia Bike Route in whole (or maybe you will), but perhaps you’ll dig pedaling it in part. For 560 miles (Washington, DC to Damascus, VA), the TransVirginia utilizes unpaved terrain from gravel to singletrack. It’s the ultimate in backpack biking.

The DC to Harrisonburg 215 is the first segment of the larger route, or you can select your own start and end points based on the Valley 520 resupply information.

Mountain Biking

Slick up your tricks with a run at Bryce Bike Park. This adventure takes you off the ground and onto unique features to sharpen your skills and reinforce your mettle. Choose from multiple trails, from the easy Sundowner to the double black diamond Hooch. Bryce Bike Park is a great place to strengthen and grow, knowing there’s help nearby if you need it.

The IMBA Epic Southern Traverse is a testy 36.4 miles that is arguably best experienced from north to south. Plan to climb 3,000 feet with the ridge of Shenandoah Mountain as your pinnacle.

Speaking of IMBA, it stands for International Mountain Bicycling Association and Harrisonburg is an IMBA Bronze Level Ride Center. According to IMBA, “Ride Centers™ feature extensive trail networks, masterfully designed for mountain bikers of every skill level and built by professional trailbuilders and local volunteers. Bring your full arsenal of bikes to these destination-worthy areas. From backcountry adventures to shuttle-served gravity trails, and from expert-only to family-friendly, you’ll encounter the best the sport has to offer.”

2022 Bicycle Races and Rides

Outfitters & Community

Guided bike tours have received an upgrade with Burg E-Bike Tours. Choose an electric bike tour on Skyline Drive through Shenandoah National Park or a Shenandoah Valley Wine Tour with three winery stops in Shenandoah County.


  • Shenandoah Bicycle Company, Harrisonburg
  • Shenandoah Mountain Touring


  • Rockfish Gap Outfitters, Waynesboro
  • Black Dog Bikes, Staunton
  • Bluestone Bike & Run, Harrisonburg
  • Rocktown Bikes, Harrisonburg

Connect with local riders when you drop in on a weekly cycling event, like the 5:30 p.m. Tuesday Night Fast Ride from the Westover Swimming Pool in Harrisonburg. It’s a 40- to 50-mile ride averaging about 20 mph.

Upcoming Routes:

We consulted the websites of Bike the Valley and Shenandoah Valley Bicycle Coalition for this article. They are essential resources for anyone interested in cycling adventures in the Shenandoah Valley.

Header image entitled “Stokesville Lodge Bicycling” is by Scott K. Brown Photography and courtesy of Virginia Tourism Corporation.

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