Biking the Shenandoah

Skyline Drive virginia overlook

Biking the Shenandoah

Biking the Shenandoah: a Magical Trip through Time and Countryside

Get ready for 6 days of biking through some of the country’s most historical countryside, and 5 nights of world-class lodging. Explore the battlefields, experience the history, and enjoy the blood-pumping pedaling of the Shenandoah and Potomac River Valleys. Travel through four states where the outcome of the Civil War was decided.


In 2012, this tour was one of the “Best Tours in North America,” from National Geographic Traveler’s Magazine Tours of a Lifetime edition.

The Shenandoah & The Civil War Bike Tour Video

Little Roundtop Gettysburg Park

Our Shenandoah bike tour is rated as intermediate to advanced, due to the elevation changes that you’ll experience rolling across this terrain. They don’t call it the Blue Ridge for nothing- you’ll be boosting yourself up and over many ridges and rollers before you pull into your lodging for the evening! If you’re up for beautiful road rides that are slightly more challenging and get your adrenaline up, this is a tour for you.

If you’re wary about the elevation changes involved in this ride, take a look at the charts below. While you will be doing some climbing, the views you’ll be rewarded with are absolutely worth the effort.


Below is a sampling of the ride elevation profiles from each day of the tour.   Keep in mind the scale of the image can distort both the steepness up and down of these rides. It might look like you’ll be climbing some intense hills, but look closely at the numbers associated with the chart– these elevation changes stretched out over a great many miles turn into much more manageable ascents.

Day 1: Leesburg to Middleburg

Shenandoah & The Civil War Trip Elevation Profile

Begin “Day 1” riding on the Washington and Old Dominion Trail in Leesburg, VA. While the elevation chart may look a little daunting, you’re highest point is only 600 feet. Over the course of the 27-mile day, you’ll lose just as much elevation as you’ll gain: up 1500 and down 1300. Tonight’s lodging is in historic Middleburg, VA at the Red Fox Inn.   The Red Fox Inn has witnessed the events shaping our country since 1728, when it began to offer hospitality to travelers.

W & OD Rail Trail
A shot along the W&OD paved trail riding out of Leesburg, VA.

Day 2: Middleburg to Marriott Ranch

Shenandoah & The Civil War Trip Elevation Profile

On Day 2, you’ll be riding through Virginia’s Hunt Country, where you’ll be gaining a little more elevation than the day before. Each day of your 6-day tour is a heavy-hitter when it comes to views, and Day 2 is no different. This 44-mile day will have you climbing roughly 2800 feet, but descending 2700. After a beautiful ride with the Blue Ridge as your constant partner in the distance, your lodging will be at the Marriott Ranch.  This is the property that JW Marriott himself chose to be the family’s private retreat because of the serenity and beauty he found here.  Today, this is the only B & B in the entire Marriott system of hotels.

Shenandoah bike tour lodging
The Marriott Ranch is a 19th-century manor house, now operating as a B&B.

Day 3: Thorton's Gap to Middletown

Shenandoah & The Civil War Trip Elevation Profile

Day 3 positions you within Shenandoah National Park, and one of the most coveted road rides in the country: Skyline Drive. Weave past (and stop to admire) some of the most incredible mountain views that Virginia has to offer. As you can see in the elevation chart, there will be some climbing today! You’ll be gaining roughly 3,500 feet over the course of the day. But what comes up must come down– you’ll be coasting down 5,100 feet in between those ascents.

Day 4: Berrysville to Harpers Ferry

Shenandoah & The Civil War Trip Elevation Profile
Biking Skyline Drive Views
One of the many views off of Skyline Drive.

Day 4 is the day of many states! You’ll be riding through three national parks and three different states all in one day’s ride. Begin in Virginia and ride towards Harper’s Ferry, WV, a town that switched hands eight times during the conflict. It’s the perfect place to grab a coffee or some roadside sustenance. After Harper’s Ferry, explore the C&O Canal Towpath on your way to Antietam National Battlefield, the site of the single bloodiest day in American history. Tonight’s lodging is at a tour favorite– The Bavarian Inn in Shepherdstown, WV.

Day 5: Shepherdstown to The Antrim

Shenandoah & The Civil War Trip Elevation Profile

Riding on Day 5 takes us out of the Potomac River Valley and into the Ridge and Valley geological province. There will be some ups and downs today, but nothing more difficult than what you’ve already accomplished thus far. Tonight’s lodging is at the Antrim 1844 Country House Hotel which served as General George Meade’s headquarters prior to the Battle of Gettysburg– and now it’s where you’ll enjoy your dinner!

The Antrim 1844 Country House Hotel Dining Room.

Day 6: Gettysburg

Shenandoah & The Civil War Trip Elevation Profile

And of course, this 6-day tour couldn’t end without a day in Gettysburg. Take a two-wheeled tour of the grounds with a licensed battlefield guide.

Today’s ride is fairly short, clocking in at just 16 miles. You’ll spend nearly all of today on the battlefield, soaking up the history and soaking in your last day on tour.

Shenandoah bike tour scenery
Just one of the many scenic country roads that make up this 6-day route.

Want to hear about other guests’ experiences on the Shenandoah tour? Click here to read Shenandoah bike tour reviews.


To check out the tour overview, follow the link for Shenandoah & The Civil War bike tour details.

Wilderness Voyageurs operates bike tours around the US, choose from road rides, rail trail tours, or mountain bike tours. We are based in Ohiopyle, Pennsylvania, right next to the Great Allegheny Passage.


Wilderness Voyageurs

103 Garrett Street

Ohiopyle PA, 15470