Shenandoah & Skyline Drive Bike Tour

Shenandoah National Park,  Skyline Drive, Gettysburg –  Ride Through Exceptional Landscapes and History

Is The Shenandoah Calling You?

Cycling joy meets historic awe. Powered by idyllic landscapes with distinct history, you’ll ride in Virginia’s genteel Hunt Country, along Shenandoah National Park’s view-tastic Skyline Drive and then north toward Gettysburg.


Retracing the key campaigns-Gettysburg, Antietam and Harpers Ferry-of the American Conflict, you’ll cycle through West Virginia, Maryland, Virginia and Pennsylvania.


Bring your camera to capture the scenery and history that dates back to the 18th & 19th centuries!


You’ll pass through battlefields big and small, including one of America’s smallest national cemeteries. Many of these towns changed hands several times over the course of the war as both armies traversed the area.


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

Tour Highlights

Visit infamous battlefields throughout Virginia, West Virginia, Pennsylvania and Maryland

Roll through Virginia's famed Hunt & Wine country

Ride the Skyline Drive of Shenandoah National Park

Personal battlefield guide at Gettysburg

Ride through 5 national parks and 4 states

Lodging Options

Red Fox Inn

Marriott Ranch

Inn at Vaucluse Spring

Bavarian Inn

Antrim 1844 Country House Hotel

Day 1: Begin riding on the Washington & Old Dominion Trail in Leesburg, VA. Pass through the cobblestone streets of Middleburg, VA, the “Horse and Hunt Capital” of the nation.


Day 2: Hear the bays of hounds as you ride through “horse and hound” country of Virginia. Visit The Plains, a buffalo hunting ground of the Sioux, and reach the foothills of the Blue Ridge just in time for dinner.


Day 3: Transport to Thornton Gap to spend the day riding in Shenandoah National Park on one of the country’s most scenic roadways– Skyline Drive.


Day 4: What a day! Three national parks and three states from the seat of your bike! Explore historic Harper’s Ferry and the C&O Canal on today’s whirlwind ride.


Day 5: Enter the Monocacy Valley via Catoctin Mountain, passing Camp David hidden in the woods. Take a step back in time for your night’s stay at the “Antrim 1844 Country House Hotel.”


Day 6: Ride north out of Maryland, crossing the Mason-Dixon line into PA. Eat a delicious lunch before going on an interpretive tour of Gettysburg National Battlefield with a licensed guide.

“Great tour for history buffs and bicycle riders.”

~Don & Jennifer Mayer

Trip Information


Trip Length - Days

New York Finger Lakes Bike Tour
Tour Type
Road Bike
Difficulty Level 4
Tour Rating
Bike Tour - National Parks - Wilderness Voyageurs
National Parks Visited
New York Finger Lakes Bike Tour Elevation
View Trip Profile

Daily Mileage

Check In Location
Leesburg, VA
PA bike tour map
Tour Area
SAG Vehicle New York Finger Lakes Bike Tour
Support & Gear Vehicle

Minimum Age


5 Breakfasts | 4 Lunches
3 Dinners

  • PP Double Occupancy

  • Single Supplement*

  • Standard Bike Rental


*This is required if you are traveling solo or if you are traveling with someone but require separate beds.


Select your departure date and click to reserve your bike tour!

  • 2020 Dates
  • If your desired date is no longer available, to be placed on a waitlist, please follow the ‘Request Itinerary’ button below & send us a message or call our office number below to speak to one of our reservation staff. We may open additional tours, and those on the waitlist receive priority on future tours