We have a flexible cancelation policy – please take a look at our cancellation policy at the time of booking. If you have any doubts please reach out and we’re happy to help.
Scheduled
6 nights
Intermediate
403 km
6934 m
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!
Road
Intermediate
67 km
3 h 20 min
Ride over Shenandoah mountain
Enjoy a ride through Virginia's 'little Switzerland' in Highland County
Experience the vibrant community of Harrisonburg
Relax at Jerfferson Hot Springs
Climb Reddish Knob and enjoy spectacular views
Stay in local guesthouses and enjoy the best of Southern hospitality
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.
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.
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.
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!
Travel to Harrisonburg, Virginia
Our first hotel
12 noon
12 noon, Harrisonburg
Full Support
Hotels & Guesthouses
Full board - breakfast, lunch and dinner
Group transfer to Harrisonburg at the end of the trip
Not included
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.
A 30% deposit will secure your place on the tour
The final balance is due 90 days before the tour departs
We have a flexible cancelation policy – please take a look at our cancellation policy at the time of booking. If you have any doubts please reach out and we’re happy to help.
We rate our tours from Level 1 (Leisure) to Level 4 (Epic). Each tour contains a description of the level, expected daily ride time, distance and elevation. If you have any doubts we’re more that happy to speak to you on the phone and help to find you the perfect trip!
We recommend that you hire a bike for your tour and will work with you after you book to help you to choose the best size and model for your ride style. If you prefer to bring your bike, it’s no problem. Please be aware that on some of our epic trips we charge a supplement to transport your bike box to our finishing location. If you have any doubts, please ask!
Insurance is not included in our tour packages. We highly recommend contracting travel insurance at the time of reservation with a company from where you are from.
Health insurance which covers you for illness or injury whilst cycling in your chosen destination is mandatory, we’ll ask you for details of your insurance providor before you travel.
