Our Tour of Virginia offers the perfect blend of moderate climbs, smooth descents, and meandering backroads, along with the cultural heartbeat of historic towns, Civil War landmarks, and Appalachian heritage.
The Shenandoah Valley is a stretch of rolling farmland, forested ridgelines, and winding rivers tucked between the Blue Ridge Mountains to the east and the Alleghenies to the west. In late September, the landscape begins to change – early fall colors paint the hillsides, the air turns crisp, and the valley becomes a cycling paradise.
The tour is designed for intermediate riders – enjoy gently rolling terrain, quiet backroads and bike-friendly communities. Stay in cosy local guesthouses and historic hotels nad enjoy the company of our local guide team!
Rated 2 out of 4 our Intermediate tours are designed for sporty people who are looking to enjoy some more challenging rides. E-bikes are available on all of our tours.
Rendesvoux with the group at our first hotel in the town of Harrisonburg. Our first ride is a relaxed loops through the surrounding farmlands. Enjoy quiet backroads and rural scenery.
Kick off the first full day of riding with our Queen Stage and take on the climb to Reddish Knob. Reddish Knob is a challenging and scenic ascent up to the very top of Reddish Knob Mountain in western Virginia. The road is narrow over part of the route and the grade is shallow to start but gradually steepens as you ride west. The last kms take us into Highland County and Virginia’s ‘Little Switzerland’. This hidden valley has more sheep than people and is know for its maple syrup. It features a cool climate at 1,000 m and is nestled in bewteen two national forests, the Monongahela to the west and George Washington to the east.
Start the day with a 5 km climb up Mountain Turnpike. Descend to High town and ride north east along the Protomac River. From New Hampton take the Hardscrabble road climb to cross the border into West Virginia and enjoy a lovely long descent to join Snowy Mountain road. From here we change course and head for home. over two climbs to finish a tough but beautiful ride.
Today we pack up and ride south to the town of Hot Springs. Our picturesque route follows a river valley to Dry Run lake. Our main challenge of the day comes late in the ride with a 4 km climb up the Mountain Valley Road. The reward is a fun descent to the base of the last climb of the day to Hot Springs.
Ride a beautiful loop to see the waterfalls at Falling Springs. On the way home climb up the ridge to ride through forests back to Hot Springs.
For our grand finale we strike a course north east to Fort Lewis on a rolling route through beautiful countryside. We end the trip at the stunning Fort Lewis Lodge, the perfect place to celebrate a week of great rides and new friendships.
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 €40 per day
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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