Overview

Your Trek Travel guides will meet you at Hotel Madison at 11:00 AM. After a 10-minute private shuttle, you’ll arrive at a local park for a signature Trek Travel picnic prepared by your guides while you get to know your fellow travelers. Following lunch, 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. You'll then set out on your first ride of the week, heading north 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

After 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 cattle and sheep farms along rolling hills as you ride the loop of your choice. Afterward, a fresh lunch at Byers Street Bistro in downtown Staunton awaits. Spend a little time wandering the centuries-old streets and appreciating the character of this historic town before you shuttle back to Harrisonburg. The afternoon is yours to discover downtown and dinner on your own at one of Harrisonburg’s many restaurants just a short walk away.

Overview

After breakfast, a 30-minute shuttle delivers you to the rural town of Stokesville, where the ride follows smooth, fast gravel roads through the densely forested foothills of the Allegheny Mountains. The road shifts between gravel and smooth pavement as you pass through Mennonite farmland and the small community of Briery Branch, with working farms and pastoral surroundings all around. Just before returning to the hotel, we’ll stop at Broad Porch Coffee for lunch and perhaps an Americano. The afternoon is yours to unwind—the hotel's indoor pool makes for a welcome end to the day before dinner at our favorite farm-to-table restaurant, Rocktown Kitchen, at your leisure.

Overview

The day's ride heads northwest from Hotel Madison after breakfast, into terrain that earns its reputation—rolling hills, twisting roads, and the kind of countryside the Shenandoah Valley is known for. Historic downtown streets give way to open farmland as the route unfolds, with three loop options letting you choose your distance before returning to town for lunch. The afternoon is your last chance to explore Harrisonburg at your own pace. The shops and restaurants of downtown are within easy reach, and the James Madison University campus, directly adjacent to the hotel, is a beautiful afternoon walk. Tonight, settle in for a final dinner of authentic Mediterranean fare at Illyria.

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. Spin 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 say farewell to your guides at the Shenandoah Valley Airport at 11:30 AM or the Charlottesville-Albemarle Airport at 12:30 PM.