Shenandoah & Skyline Drive Bike Tour

Is The Shenandoah Calling You?

Our Shenandoah bike tour is a sumptuous blend of Civil War-era historic sites and idyllic classic American landscapes. This is a true Inn-to-Inn cycling vacation where you’ll make your way through four states, cycling almost exclusively door-to-door to five stunning B&Bs. You’ll ride through Virginia’s genteel Hunt & Wine Country, along Shenandoah National Park’s gorgeous Skyline Drive, down into Harper’s Ferry, West Virginia, up over Maryland’s Catoctin Mountains, and finish in historic Gettysburg, Pennsylvania.

Whether fully human-powered, or assisted by an E-bike, these are some of the most beautiful bicycle routes that you could ever hope to ride, and just can’t be missed! Breathtaking Blue Ridge overlooks, pastoral valley farms, and winding mountain passes provide the setting for this incredibly diverse tour. Ride along open rolling farm roads, up quiet forest passes, and alongside water-lined valleys, all virtually free of cars.

Off the bike, you will have the opportunity to visit an award-winning Virginia winery, walk the cobblestone streets of Harpers Ferry and the Appalachian Trail, and indulge in two private, multi-course dinners at our majestic B&B dining rooms. Bringing extra color to your Mid-Atlantic experience, we’ll retrace the Civil War’s key campaigns in Gettysburg & Antietam, by bicycle, with a personal tour guide. With time to rest and relax in five distinctive B&B’s – two in beautiful country settings, and three in downtown historic districts – the Shenandoah & Skyline adventure is the perfect active getaway.

Custom bike tour departures available for groups of 6 or more.

Day 1:  After getting to know one another, we start this Inn-to-Inn cycle tour, riding directly from our initial meeting point in Leesburg, to the first hotel in downtown Middleburg. First, we warm our legs up with a paved section of the Washington & Old Dominion Trail. By the time you depart the “W, O & D” and hit the streets, you’ll have escaped the hustle and bustle of the D.C. metro, and will relax into six days of quiet cycling. After enjoying lunch in the park, we will pedal directly to a post-ride celebratory drink at Boxwood Estate; a highly respected winery in Northern Virginia that focuses on Bordeaux-style wines. You can then choose to hang up your cycling shoes and check in to the stunning Red Fox Inn, or get some more miles in the “The Nation’s Horse and Hunt Capital”. Middleburg is upscale in an inviting way, with a long downtown strip, lined with boutique shops and many high-quality dining options to choose from.

Day 2: In the peaceful early morning hours, as we depart from the Red Fox Inn on our bicycles, you may hear the bays of hounds as we travel through “horse and hound” country, making our way west toward Shenandoah National Park. Today, you will be hard-pressed to find a section of this ride with a view that would disappoint. This is some of the most magical riding on the East Coast!  Mile after mile of fun, tiny climbs and descents, give you endless views onto massive historic estates, surrounded by hand-built stone fencing from centuries past. Tonight, we get to stay at one of the most exclusive of these private estates: the Marriott Ranch. This 4,200-acre pastured cattle farm, with sweeping views of the Blue Ridge Mountains, was one of the residences of J. Willard Marriott Sr., the founder of what is today Marriott International. Happy hour, with more local wine & cheese on the covered porch, is followed by a multicoursed meal at a dining table that once held many American dignitaries.

Day 3: This morning, we shuttle up to the top of Shenandoah National Park, and after a group picture overlooking the “bread basket of the Mid-Atlantic” far below, we begin the roller coaster ride of Skyline Drive. What a bucket list ride today!  Slow, steady climbs are rewarded with both easterly and westerly overlooks, and riveting extended descents. Since we are cycling Skyline Drive during the mid-week, you may feel as though you have the entire National Park to yourself. Lunch at the visitor center is followed by your first chance for local ice cream as you descend out of the Park and into the mountain town of Front Royal. Continue onward directly to our lodging for the evening, the French-inspired, L’Auberge Provencale. These rooms are an escape in and of themselves, and you’ll have plenty of time to rest and relax in their beauty and comfort. 

Day 4: Three national parks and three states from the seat of your bike today! Today’s ride is a mix of forested, historic battlefield roads, and gorgeous water-lined rides alongside the Shenandoah and Potomac Rivers, and even a section on the C&O Canal. You will have time to explore Harper’s Ferry in all its historic and outdoorsy glory. This small town was the center of many important battles and Presidential speeches, and is the confluence of two giant rivers, and the unofficial “halfway point on the Appalachian Trail”. This action-packed day is capped off with a private guided cycling tour of Antietam battlefield, finishing at one of the most iconic ice cream shops in the Mid-Atlantic. Reenergized, you will pedal straight to the Bavarian Inn, perched high over the Potomac River.

Day 5: A big German-style buffet breakfast this morning will fuel us for the big day ahead in the saddle. Today, you will impress your friends as you ride 50 miles, up and over Maryland’s Catoctin Mountains, once again door-to-door, with your luggage waiting patiently for you in your room at the Antrim 1844. This ride seems to resemble the land that cars forgot, as you’ll feel like you have the forested and pasture-lined roads all to yourself. Keep your eye out for Camp David, hidden deep in the woods, and don’t miss the many tumbling falls as you descend over the backside of the mountains. Celebrate your accomplishment with tea and cookies on the veranda overlooking the meticulously manicured and colorful gardens. Tonight, you will indulge in a meal to remember for a lifetime, as we work our way through five Farm-to-Table courses in our grandiose private dining room, which once fed General Meade and his cabinet.

Day 6: Your final ride of this incredible adventure brings a new set of sights and more local knowledge to take home. Choose either a long, arching ride, through southern Pennsylvania’s white-fenced farmland or a more direct route that allows you time to explore Gettysburg National Park’s robust and remarkable visitor center. Whichever option you pick, we will all meet with our private tour guide for a final picnic lunch and then follow him on our bikes for another interpretive cycling tour of Gettysburg National Battlefield.