Shenandoah Valley 4-Day Bike Tour

Meet your guides at The Westin Washington at Dulles Airport for a transfer to our hotel, an impeccable country manor at the base of the Blue Ridge Mountains. We’ll kick things off with a bike fitting and safety briefing in preparation for our first ride through the country: cycle past farmlands lined with sweetgum trees and horses roaming rolling pastures until we reach the village of Washington. Don’t let the tiny town square deceive you—Washington is incubating a major farm-to-table movement and has become the booming culinary capital of the Shenandoah Valley. Ride on to our first taste of gourmet Virginia at our friend Reynold’s farm. His cabin, which dates back to the 16th century, once served as a toll house on an early turnpike, where travelers paid fees to help improve the roads. Enjoy a tour of the property and sample his wines, then settle in for a delightful picnic lunch prepared by your guides. Pedal back to our hotel and regroup for a cocktail before dinner at our favorite local restaurant.

Meals: Lunch / Dinner
Destinations: Huntly, Washington, Massanova
Accomplished: 28 miles/ 46 km, elevation gain: 2,380 / 852 meters
Longer Option: 35 miles / 56 km, elevation gain: 2,800 feet / 852 meters
Accommodations: Glen Gordon Manor

Today we ride east through a landscape that looks just like the 19th-century painter Sanford Gifford depicted it: wooden fences, wide-open sky, and the Blue Ridge Mountains bathed in golden light. You can almost see the fox hunts on Gilded Age estates and imagine horses galloping wildly through the rural idylls. Instead, we’re taking our steeds to visit our good friend and local butcher, Amanda, for a meal to remember. After lunch, round out the gourmet day with an exclusive visit to one of Virginia’s top wineries and sample Bordeaux-style blends that give French wines a run for their money. This evening, our friends Reem and Andrea host us for an intimate dinner focused on dishes that recall Andrea’s native Italy.

Meals: Breakfast / Lunch / Dinner
Destinations: Marshall, Delaplane, Markham
Accomplished: 30 miles / 48 km, elevation gain: 1,637 feet / 499 meters
Longer Option: 51 miles / 83 km, elevation gain: 3,064 feet / 934 meters
Accommodations: Glen Gordon Manor

This morning’s ride begins from the Front Royal entrance to Skyline Drive, a road that spans the entirety of Shenandoah National Park. Built by the Civilian Conservation Corps in the 1930s, Skyline Drive traverses the spine of the Blue Ridge Mountains and makes for some pretty hearty climbs—and just as many beautiful vantage points. Once we reach the heights of Hogback Overlook, each subsequent climb is a bit lower on a rollercoaster descent into Thornton Gap. This historic mountain pass was used by Stonewall Jackson to conceal his foot cavalry as they traveled between the Valley and the Piedmont region during the Civil War. From there it’s just a few more miles to the quaint town of Sperryville, where we’ll celebrate a full day of riding with a great spread at a hip foodie restaurant. After lunch, transfer back to the hotel. Treat yourself to a massage in the spa or relax by the pool. This evening, chef-owner Dayn Smith invites us into the hotel’s Houndstooth Restaurant for a memorable final meal.

Meals: Breakfast / Lunch / Dinner
Destinations: Skyline Drive, Thornton Gap, Sperryville
Accomplished: 28 miles / 46 km, elevation gain: 3,250 feet / 981 meters
Longer Option: 58 miles / 93 km, elevation gain: 4,680 feet / 1,451 meters
Accommodations: Glen Gordon Manor

Fit in one final ride after breakfast. Our route is centered around the local farms that are pioneering a sustainability movement and bringing organic farming to the Valley—which in turn has nurtured a boom in innovative restaurants. For our last meal together, we’ll share a home-cooked lunch at our friend’s farm that celebrates the bounty of ingredients grown in the area. We’ll send you on your way with a full heart and full stomach.

Meals: Breakfast / Lunch
Destinations: Hume, Huntly
Accomplished: 24 miles / 38 km, elevation gain: 1,273 feet / 388 meters