My tour

Northern Shenandoah Valley



This bike tour is full of American history and leads you through the Northern Shenandoah Valley of Virginia. The roads are all paved, mostly rural with light vehicular traffic.

8 days
490 km / 304 mi
$ 1,590.-
  • Tour starts every Sunday; other days also possible.
  • Luxurious, authentic B&B accommodation.
  • Meals included: 7 breakfasts, 3 dinners.
  • This tour's length can be increased or decreased by a day.
  • Luggage transport for additional fee (except for participants from Europe).
  • In the fall foliage season room accommodation can be difficult and can carry a premium.



8 days
Easy = untrained, normal physical condition
Moderate = regular cyclist, good condition
Challenging = experienced, well trained
Guided = with cycling guide(s) - support van
Self Guided = individual - directions+maps
Daily distance
60-80 km / 37-50 mi
Total distance
490 km / 304 mi
Deluxe = 4-5 star hotel or excellent B&B
Basic = 1-2 star hotel/motel or B&B
Camping = tent, sports hall or campus
Deluxe, half board
Luggage transport
Daily luggage transfers
06 May 2019 - 27 Oct 2019
Winchester (13.00)
Winchester (11.00)
Washington airports
Airport at start
Washington Dulles Int. Airport (IAD)
Airport at finish
Washington Dulles Int. Airport (IAD)


Price per person
The tour price per person
$ 1,590.-
bike available for rent
ask for quote for bike rental
Single supplement
If you travel alone a single supplement is charged. With some group tours you can avoid a single supplement by sharing a room with another rider.
$ 700.-


Day 1:

Arrive at your Bed & Breakfast (B&B) in Winchester and meet the tour company representative to review the tour details. Winchester is a delightful place to simply stroll through the main historic street and the surrounding historic neighborhood to view the period architecture.

Day 2:

50 mi / 79 km
A loop ride from Winchester will take approximately 56 miles through rural Frederick, Clark and Warren counties following the Shenandoah River and back to Winchester. After the day’s biking enjoy dinner on the Pedestrian Mall in historic downtown Winchester.

Day 3:

37 mi / 59 km
Today’s ride will take you from Winchester to Strasburg. This ride will take you through the Northern Shenandoah Valley between the Massanutten Mountain and the Allegheny Mountains.

Day 4:

38 mi / 61 km
Strasburg to Woodstock is a beautiful ride through Fort Valley and over the Massanutten Mountain into Edinburg then onto Woodstock where you will overnight.

Day 5:

38 mi / 61 km
Today you bike from Woodstock on a ride that follows gently rolling country roads through fields and farms with spectacular views of the Valley and mountain ranges on both sides. You will follow the North Fork of the Shenandoah River which you cross to go through the Meems Bottom Covered Bridge. At ride’s end you will be at the Widow Kip’s Country Inn in Mt. Jackson for your night’s lodging and a relaxing afternoon.

Day 6:

40 mi / 64 km
Today you bike from Mount Jackson to Strasburg. Your route will take you through the Fishers Hill Battlefield, along the North Fork of the Shenandoah and into Strasburg or Middletown were you will overnight.

Day 7:

34 mi / 54 km
Your ride today will take you past the Cedar Creek Battlefield and Belle Grove Mansion into Winchester and returns you to your starting location in Winchester over different roads than your ride from Winchester but with similar topography.

Day 8:

Departure from your B&B in Winchester at your leisure after breakfast.

Map & Routes



rental-bike rentals are available
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