Self-Guided Tours

Northern Shenandoah Tour

Our Northern Shenandoah Valley Biking Tour begins in Winchester and works south. Scenic country roads through rolling hills, farmlands, and past wineries, apple orchards and civil war battle sites are just some of what you will experience each day on our tour through the northern Shenandoah Valley. This Virginia cycling tour is rated easy to moderate; easy because of many long, flat stretches, and moderate because of some climbs, a few of which are steep as well as stretches of country roads over rolling terrain.

Day 1

Arrive in Winchester and settle into your accommodations. On your schedule, you will meet with the Virginia Bicycling Adventures representative for a tour orientation. After which you can relax and contemplate the week's rides or explore the town. It is a delightful place to simply stroll through the main street shops and to visit the restaurants or the surrounding historic neighborhood to view the period architecture. With numerous antique stores, the eclectic Pedestrian Mall, several museums, and the historic district to browse and explore, Winchester is an excellent example of the ambiance of the Shenandoah Valley. Established before the Revolutionary War and a hub of activity during the Civil War, Winchester has a long and deep history. Close the evening with a relaxing dinner on the Pedestrian Mall.

Day 2

Today's ride is a 52 mile excursion through three northern Shenandoah counties. After riding over city streets out of Winchester this ride will take you to pleasant rural roads through Frederick, Clarke and Warren counties.This is a relaxing ride through the countryside that even offers opportunities to wade in the south side of the river which is shallow and near a low water, one lane bridge.

After the day’s ride you can relax by touring the historic district or visiting some local shops, art galleries, museums, or spending the evening on the pedestrian mall and dining.

Day 3

After breakfast, and on you own time schedule, you can venture off on the day's ride which will take you out of Winchester through the countryside of rural Frederick county. This loop ride will take you approximately 35 miles over rolling country roads through farm lands and small villages and will be an excellent opportunity to just enjoy the scenery of the Shenandoah Valley along the Allegheny Mountains which are the western edge of the Valley. You return to Winchester and after a short drive you arrive at you evening's accommodations in Strasburg. It is a delightful place to simply stroll through the surrounding historic neighborhood to view the period architecture. Strasburg also has numerous antique stores, a large antique emporium, several museums, and a cavern to browse and explore. Close the evening with a relaxing dinner.

Day 4

Today you will bike from Strasburg to Middletown past two Civil War Battlefields to Round Hill then along the Shenandoah River and back to Strasburg. This ride is approximately 38 miles taking you through rural areas of the Shenandoah Valley between the Massanutten Mountain and the Allegheny Mountains. After a leisurely drive to Woodstock and your accommodations on the Shenandoah River enjoy dinner in one of several local restaurants.

Day 5

After breakfast you bike from Woodstock on a ride of 38 miles that follows gently rolling country roads through fields and farms with spectacular views of the Valley and mountain ranges on both sides to Edinburg. Leaving Edinburg you will follow the North Fork of the Shenandoah River to Mt Jackson where you can take a short detour across the Meems Bottom Wooden Bridge which is the longest covered bridge in Virginia. Your return back to Woodstock will pass several wineries over typical Virginia rural roads with small rolling grades and very low traffic.

Day 6

After a leisurely breakfast you can leave on your own schedule.

  • The cost of the Northern Shenandoah Valley Tour as described is $797 per person/double occupancy; the single supplement is $390. A non-B&B tour can be arranged with a cost of $624 per person/double occupancy; the single supplement is $310
  • This tour is rated easy to moderate because of rolling country roads and some climbs, a few of which are steep.
  • Your accommodations will be in excellent B&Bs or equivalent hotels due to availability. After booking accommodations, we can furnish links. Your package includes five full breakfasts, a lunch and two dinners. You will have arrival orientation, comprehensive route instructions, supporting maps, and emergency support.
  • This tour can be booked between March 30 and October 31 and is generally scheduled to start Sunday evening and end Friday morning; however other start and end days are workable as well, but at certain times of the seasons and on most weekends, room accommodations can be difficult and can carry a premium. With adequate lead time, these can often be overcome.
  • This tour can be extended one or two days to allow more biking. If this is of interest, please contact us to discuss options.