Ride an incredible gravel adventure through Virginia’s Shenandoah Valley and the rugged Allegheny Highlands. From rolling farmland and quiet country roads to remote forest climbs and ridgeline views, this route blends Appalachian charm with wild backcountry challenge. Evenings finish with hand-cooked meals, historic inns, and mountain hospitality — the perfect reward after days of big climbs and unforgettable scenery.
The tour is designed for advanced riders – enjoy rolling terrain, quiet backroads and bike-friendly communities. Stay in cosy local guesthouses and historic hotels and enjoy the company of our local guide team!
Rated 3 out of 4 our Advanced tours are designed for people who ride regularly and want back to back challenging days on the bike. Riders should be confident riding in a small group, comfortable on extended climbs (at your own pace) and have good bike handling skills on corners and descents. E-bikes are available on all of our tours.
Rendesvoux with the group at our first hotel in the town of Harrisonburg. Enjoy an easy warm-up spin to Singers Glen, the birthplaces of gospel music. This is classic Shenandoah Valley gravel – enjoy rolling farmland, country churches and Appalachian charm.
The ride winds through maple country landscapes and the bucolic farmland of the Shenandoah Valley, following quiet gravel lanes past scenic barns and pastoral countryside. From there, the route takes on a big climb into George Washington National Forest before crossing into West Virginia, where twisting ascents open up to sweeping mountain views.
The route rolls west along the Mountain Turnpike before turning onto Doug Bank Road, where stunning Highland County scenery sets the tone. A big climb over Mad Sheep and Mad Tom Mountains reaches the tour’s high point at 4,390 feet (1,338 meters), followed by a rugged stretch of 12 miles on Allegheny Road through remote wilderness gravel. From there, the ride threads through Rider Gap and High Top before descending toward Lake Moomaw, culminating in a dramatic finale through Richardson Gorge.
The day begins with a climb up Warm Springs Mountain, leading to Skyline Ridge Road, a four-mile ridgeline traverse with sweeping views across the hardwood forest. A fast descent drops east into the valley before the route winds over the serpentine gravel of Piney Mountain and flows along paved stretches through Burnsville and Williamsville. From there, Sugar Tree Lane—known as the Lost Gravel Highway—guides riders toward a fitting finale at Fort Lewis Lodge, where rustic charm and a legendary fried chicken feast await.
The ride begins in Marble Valley, tracing rarely ridden gravel along Walker Mountain and the quiet backroads of Marble Valley. From there, the route climbs Cold Springs Road before crossing the historic Staunton–Parkersburg Turnpike. Rolling fast gravel leads into a smooth descent back into the valley, finishing in Staunton, Virginia, where a celebration party awaits at Oakdean Lodge.
Sadly it’s time to say goodbye! A group transfer departs for Harrisonburg at 10:00 am.
Full Support
Enjoy small group sizes and professional, personal support all week from your guides & support vehicle.
We work with an industry leading guide to guest ratio – expect up to 4 guests per guide on the trip with guides leading the way on the road and a support vehicle close by at all times. Note that for groups of 4 riders or less this tour is run as a guided trip without the support vehicle.
The ride support vehicle is stocked with natural ride nutrition, electrolytes and water, as well as a full set of tools to resolve any mechanicals. On selected days the support crew will serve a delicious picnic lunch in a scenic location en route. Enjoy local foods chosen to keep you feeling energized and healthy.
Eat Sleep Cycle guides are experienced riders from all walks of life united by a love of cycling who’ll help to keep the group safe, motivated and savouring the trip of a lifetime.
All guests will receive access to our digital Road Book and routes, giving everyone the flexibility to ride at their own pace.
Hotels shown are examples and are subject to change
By the Side of the Road was originally established in 1999 as Harrisonburg, Virginia’s first bed and breakfast business. Founders Dennis and Janice Fitzgerald wrote the city ordinance that defined the services of a fine B&B establishment in the region and as of June 2022, their daugther and son-in-law, Anna & Jesse have taken on the Inn. A perfect family-run establishment to kick off the trip close to the buzzing town centre of Harrisonburg.
Monterey Inn, newly established in 2023 within a stunning 1905 Victorian structure, lies at the heart of “downtown” Monterey Virginia – a quaint mountain town that is the county seat of Virginia’s Highland County. This serene and picturesque location rests deep in Virginia’s Allegheny Highlands, that form the western border of the captivating Shenandoah Valley.
Vine Cottage Inn has been welcoming travellers since 1905. Expect a warm welcome and a comfortable stay! Tammy and Dave are resident Innkeepers at Vine Cottage Inn and are thrilled to have the opportunity to continue the long history of exceptional hospitality for which the Vine is known.
Fort Lewis Lodge is set on a 3,300-acre mountain farm with a river running through it. Family owned and operated for over 65 years, the lodge offers a spectacular finish to the trip. Rustic decor mingles with contemporary elegance. Enjoy home-cooked food in a spectacular setting.
Bike hire is not included in the tour. Add bike rental to the trip from €60 per day.Bikes shown here are examples and are subject to availabilty at the time of booking. We'll let you know the available options in your size when you book with us.
Jeremiah Bishop is an accomplished American professional cyclist renowned for his versatility and success in a variety of disciplines, particularly in mountain biking and gravel racing, where he has multiple national titles. Outside of racing, Bishop is a dedicated ambassador for cycling and is known for his contributions to the development of the cycling community in his home state of Virginia. Jeremiah is an all-round legend of the cycling world and we are delighted to welcome him to our guide team!
Virginia is quickly becoming one of the premier destinations for road and gravel cycling enthusiasts, offering a diverse range of terrain that caters to all levels of riders. From the rolling hills and scenic byways of the Shenandoah Valley to the rugged, unpaved paths through the Appalachian foothills, Virginia combines stunning natural beauty with challenging courses that will test both your endurance and your skills. Cyclists can explore quiet, country roads lined with vineyards and historic landmarks, or push through remote gravel routes where the only sounds are the crunch of tires on dirt and the call of wildlife. With mild weather year-round, a welcoming cycling community, and events like the Shenandoah Mountain 100, Virginia is the perfect spot for your next cycling adventure. Whether you’re chasing personal records or simply seeking an unforgettable ride, Virginia has something for everyone.
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