Overview

Your Trek Travel guides will meet you at Hotel Madison at 11:00 AM on the first day of the trip. After a 30-minute private shuttle, you’ll arrive in the small community of Briery Branch. Enjoy a picnic lunch prepared by your guides and get to know your fellow travelers. After a short round of introductions, your guides will discuss the rules of bike safety and specific cycling tips for riding in the Shenandoah Valley before familiarizing you with your Trek Checkpoint gravel bike and ensuring a comfortable fit. Afterward you'll set out on your first ride of the week, which traverses the farmland west of Harrisonburg. Long range views and well-kept farms abound as you get your first taste of the gravel roads of the Shenandoah Valley. Once back at Hotel Madison, take some time to settle into your room before dinner. This evening, enjoy a short walk with the group into downtown Harrisonburg for Italian-inspired dishes and wood-fired pizza at Bella Luna.

Overview

Following breakfast, you'll shuttle 40 minutes to the town of Shenandoah for a blend of local history and excellent gravel forest roads. Begin by riding through this former iron town, which took on the Shenandoah name in 1890 to reflect its place in the valley. After crossing the South Fork of the Shenandoah River, you'll pass Catherine's Furnace—a relic of the 1840s iron industry—before enjoying miles of quiet gravel along Cub Run Road. Riders seeking an extra challenge can add an out-and-back climb to Emerald Pond, while the rest of the group continues along Cub Run Road toward the river. You’ll regroup on its banks for a casual picnic lunch. Afterward, we’ll return to the hotel with time to relax or explore downtown. This evening, you’re on your own for dinner, with Harrisonburg’s many restaurants just a short walk away.

Overview

After fueling up for the day you'll ride from Hotel Madison to explore the roads that lie to the northwest of Harrisonburg. As with the first two days, you can expect a lot of twists and turns and consistently hilly terrain. You'll ride through historic downtown and neighborhood roads before transitioning into the pastoral countryside that defines so much of the Shenandoah Valley. With three loop options to choose from, you can decide how many miles you want to pedal before returning to town for lunch of your choice. This afternoon is your opportunity to walk around downtown and visit the shops and restaurants of Harrisonburg. The campus of James Madison University is adjacent to our hotel and also makes for a beautiful walk. This evening we will reconvene for casual fare at a local restaurant to refuel for our "queen's stage" tomorrow.

Overview

Following breakfast, you'll board a private shuttle for a 40-minute ride to our favorite coffee shop in Staunton, known as the Queen City of the Shenandoah Valley. From here, begin a challenging and incredibly scenic loop ride through the farms and forests south of town. The road shifts from pavement to gravel and back again several times throughout today’s routes, offering a mix of textures and terrain. Take in views of historic mills, weathered barns, and rolling cattle and sheep farms as you ride the loop of your choice. Afterward, enjoy a fresh lunch at Byers Street Bistro in downtown Staunton. Spend a little time wandering the centuries-old streets and appreciating the character of this historic town before you shuttle back to Harrisonburg and settle in for your final farm-to-table dinner at the lively Rocktown Kitchen.

Overview

For this morning's final ride, you'll head out to the east of Harrisonburg for a paved loop through the tiny community of Keezletown. Enjoy spinning along Mountain Valley Road with views of Massanutten Mountain before returning to the hotel to prepare for departure. If you’d rather relax, you are welcome to sleep in and enjoy a leisurely breakfast. A private Trek Travel shuttle will depart from the hotel at 11:00 AM. You’ll then say farewell to your guides at the Shenandoah Valley Airport at 11:30 AM or the Charlottesville-Albemarle Airport at 12:30 PM.