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Shenandoah Valley Bike Tour

Appalachia + the Blue Ridge Mountains: from Harpers Ferry to Skyline Drive in Civil War Virginia

6 days / 5 nights Level: 3Price From: $4,995Collection: Classic

Tour Highlights

  • Bike through the cradle of the Civil War, visiting Harpers Ferry, Antietam, and Winchester to immerse yourself in this chapter of American history
  • Uncover Virginia’s unexpected gourmet identity with wine tastings and a three-Michelin-star dinner at The Inn at Little Washington
  • Conquer a challenging ride on Skyline Drive, the scenic route running along the crest of the Blue Ridge Mountains in Shenandoah National Park
  • Stay at a spate of historic inns and boutique manors that radiate American charm
  • Explore Appalachia as you cycle through the Shenandoah Valley, covering three states: Maryland, West Virginia, and Virginia


Country ham, mountain trout, heirloom apples


Ciders, craft micro-brews, and local Virginia wines like Chardonnay and Cabernet Franc

Print Itinerary
  • Day 1

    Welcome to Winchester

    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.

    Meals: Lunch / Dinner
    Destinations: Summit Point, Jordan Springs, Winchester
    Accomplished: 21 miles / 34 km, elevation gain: 686 feet / 209 meters
    Longer Option: 35 miles / 57 km, elevation gain: 1,483 feet / 452 meters
    Accommodations: Hillbrook Inn

  • Day 2

    The Civil War at Harpers Ferry and Antietam

    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.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Harpers Ferry, Antietam, Sharpsburg
    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
    Accommodations: Hillbrook Inn

  • Day 3

    Rolling Appalachia

    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.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Millwood, Front Royal, Huntly
    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
    Accommodations: Glen Gordon Manor

  • Day 4

    Skyline Drive

    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.

    Meals: Breakfast / Lunch
    Destinations: Fort Royal, Skyline Drive, Sperryville, Washington
    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
    Accommodations: The Inn at Little Washington

  • Day 5

    Virginia is for Foodies

    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.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Rock Mills, Massanova, Flint Hill
    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
    Accommodations: The Inn at Little Washington

  • Day 6

    Take Me Home, Country Roads

    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).

    Meals: Breakfast
    Destinations: Washington
    Accomplished: optional ride

DuVine itineraries may be subject to slight route changes, hotel substitutions, and other modifications.

Arrival Details

Airport City: Washington, DC Pick-Up Location: Dulles Airport, downtown DC, or Hillbrook Inn Pick-Up Time: 10:30 am at Hillbrook Inn
Departure Details

Airport City: Washington, DC Drop-Off Location: Dulles Airport or Hillbrook Inn Drop-Off Time: 11:00 am
COVID-19 Travel Restrictions

For the latest travel restrictions related to the coronavirus pandemic⁠—including quarantine requirements—please review Virginia’s state travel guidelines.

Any scheduled tour can be made private. Your group, your dates. Go Private

2021Single Supplement From: $1,200

See our cancellation policy

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  • Thoughtfully selected accommodations that reveal the true character of the region
  • Luggage transfers


  • Daily breakfasts, all lunches, nutritious snacks, and après velo cocktails
  • 4 gourmet dinners at our favorite local restaurants and renowned culinary establishments
  • Carefully selected local wine, beer, or spirits with every meal


  • Wine tastings and activities as outlined in the tour itinerary
  • Entrance fees to historic sites, museums, parks, and all other exclusive events
  • Gratuities for baggage, porters, and hotel service


  • Top-of-the-line bicycle selection
  • Bike helmet
  • Complimentary DuVine gear, including a custom cycling jersey, DuVine t-shirt, water bottle, and drawstring bag
  • GPS in most destinations


  • Expert bilingual guides with extensive local knowledge
  • Support vehicle that follows the day’s route, distributes refreshments, and offers lifts
  • Pick-up and drop-off before and after your tour from predetermined meeting points
  • Daily bike maintenance to ensure optimal performance

See our FAQs page for answers to common questions.

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Synapse Carbon Disc Ultegra Di2

Manufacturer: Cannondale

Type: Road

Quick 1 Disc

Manufacturer: Cannondale

Type: Hybrid

Electric Assist

Type: E-Bike