Meet your guides at the Hillbrook Inn or in Washington DC for a transfer to the hotel. We’ll kick things off with a bike fitting and safety briefing in preparation for our first ride through the gorgeous, sprawling farmland of the Shenandoah Valley. Stop at a local farm where we’re treated to a seasonal lunch, then choose to ride straight back to Hillbrook Inn or take a longer route to Third Winchester Battlefield. The city of Winchester witnessed three major battles in the Civil War, causing it to change hands over 70 times and earn the nickname “the shuttlecock of the Confederacy.” After a dose of Civil War history, regroup for dinner at our hotel’s cozy, country-chic restaurant.

Accomplished: 21 miles / 34 km, elevation gain: 686 feet / 209 meters

Longer Option: 35 miles / 57 km, elevation gain: 1,483 feet / 452 meters

Harpers Ferry played a critical role in the Civil War: in 1859, an ill-fated raid on the federal armory escalated the tense national political landscape to a fever pitch. While still steeped in history, today Harpers Ferry is a charming town brimming with historic inns and quaint shops at the intersection of the Potomac and Shenandoah Rivers. We’ll pedal here for a coffee and a chance to look around, then ride across the Potomac into Maryland. Spin along the Chesapeake and Ohio Canal towpath (or “C&O” to those in the know) to the Antietam Battlefield, a national park commemorating the bloodiest day in American history. While not exactly a victory for the Union, Antietam gave Lincoln the political cover to make the Emancipation Proclamation. Have a picnic lunch before a guided tour of the battlefield, then round out the day riding (or transferring) back to Hillbrook.

Accomplished: 55 miles / 88 km, elevation gain: 2,414 feet / 736 meters

Shorter Option: 31 miles / 50 km, elevation gain: 1,610 feet / 491 meters

Today we ride south into Virginia through the leafy heart of the Shenandoah Valley, where General Stonewall Jackson mounted his most essential Confederate campaigns. Later in the Civil War, the Valley once again became a key player in battle when the destruction of its important farms and crops helped nudge Lee and the Confederacy to their final defeat. Biking through the landscape here is just as the painter Sanford Gifford depicted it during the 19th century: wooden fences, wide-open sky, and the Blue Ridge Mountains bathed in golden light. We’ll stop at a local general store for a slice of pre-lunch pie, then finish off the meal at one of Virginia’s top wineries. Tonight, stay at a peaceful country manor and enjoy a farm-to-table dinner prepared by the award-winning chef.

Accomplished: 43 miles / 69 km, elevation gain: 2,221 feet / 677 meters

Shorter Option: 33 miles / 53 km, elevation gain: 1,473 feet / 449 meters

This morning, warm up on a ride over the Chester Gap into Front Royal, following the path Robert E. Lee took through the mountains while advancing into (and retreating from) Gettysburg. Nowadays, the town of Front Royal is better known as the 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, begin a thrilling descent through Thornton Gap and arrive at our Relais & Châteaux hotel in the village of Washington. Settle in, stroll the grounds, and choose from the charming restaurants in and around Washington for dinner on your own this evening.

Accomplished: 42 miles / 67 km, elevation gain: 3,060 feet / 933 meters

Longer Option: 57 miles / 92 km, elevation gain: 5,514 feet / 1,681 meters

The day begins with a ride through Rappahannock County, often called the “Sonoma of the South” for its concentration of wineries, restaurants, and pleasant country scenery to the east of the Blue Ridge Mountains. Our route is a bit of a farm trail treasure hunt: we’ll meet with a handful of farmers who are pioneering the area’s emerging sustainability movement, and collect a souvenir picnic ingredient at every stop. Finally, it’s time to enjoy the bounty we’ve amassed as we assemble all our home-grown produce into a farmyard picnic. What better way to end a foodie’s perfect day that tonight’s dinner at our hotel’s three-Michelin-star restaurant, which is widely considered one of the top culinary institutions in the country.

Accomplished: 36 miles / 58 km, elevation gain: 2,463 feet / 751 meters

Shorter Option: 26 miles / 42 km, elevation gain: 1,804 feet / 550 meters

Sleep in and enjoy our last morning at the historic inn, or wake early for one final spin through the Blue Ridge foothills. We’ll say our farewells at Dulles International Airport (or back at Hillbrook Inn for those within driving distance).