Self-Guided Tours
Southern Shenandoah Tour

Our Extended Southern Shenandoah Valley Bicycle Tour begins in Staunton and goes south through the Shenandoah Valley and back to your starting location in Staunton. You will bicycle over scenic country roads through rolling hills, farmlands, awesome mountain vistas and challenging climbs. These are just some of what you will experience each day on our extended tour through the southern Shenandoah Valley. This Self-Guided tour is rated moderately difficult; although there are many flat stretches, several of the rides are long, mostly on rolling country roads with climbs, a few of which are steep.

Day 1

Arrive at your B&B in Staunton and meet with the Virginia Bicycling Adventures representative to review the tour details.

Day 2

Your ride of 35 miles departs Staunton to the northwest into the heart of the Shenandoah Valley along the Allegheny Mountains where you will soon reach farmlands that once supported the Armies of the Confederacy. At Mt. Solon you can take a 1.6 mile round trip option into Natural Chimneys Regional Park for a nice mid-afternoon break. You will continue your ride back to Staunton over rolling country roads that become a little hillier as you near the city. After the day's ride of 35 miles, or 37 if the Natural Chimneys option is taken, you can relax by touring the historic districts or visiting some local shops, art galleries, museums, or spending the evening at the Blackfriar's Playhouse and dining.This ride can be expanded to 54 miles.

Day 3

Today you bike 40 miles from Staunton into the western edge of the southern Shenandoah Valley alongside the Allegheny Mountains into Goshen. This ride is over rolling rural roads with a few steeper climbs but it is quite scenic with varying terrain, challenge and topography. Your B&B for the night is in Goshen.

Day 4

Your ride to Lexington through the Goshen Pass is along the Maury River cut to Rockbridge Springs and on into Lexington. This shorter ride of 24 miles is through one of the most scenic and traveled roads during the fall foliage season. Lexington, where you will overnight, is a town that is consistently rated as one of the best small towns in America. Lexington is steeped in Civil War history with the Virginia Military Institute, and burial chapel of Robert E. Lee, General of the Armies of the Confederacy which is on the campus of Washington & Lee University.

Day 5

Today's route of 44 miles is on some of the best and tranquil biking roads in the southern valley. Departing Lexington heading south you soon enter seemingly endless countryside on mile after mile of roads almost totally absent vehicles. As you make the turn north, you will encounter hillier terrain with a constant but not steep elevation gain followed by an 11 mile gradual down hill run along a creek on one of Virginia's best biking roads. Approaching Lexington, you will climb a succession of hills that set you up for a two mile decent into Lexington. The remainder of the day can be spent touring the many historic sites, homes, and shops that Lexington offers or just relaxing at your B&B.

Day 6

On today's ride of 47 miles to Waynesboro and after leaving Lexington you soon will enter seemingly endless uninhabited countryside. Your route goes north following the base of the Blue Ridge Mountains and is mostly through rural countryside for the initial 30 miles. After arriving in the Town of Stuarts Draft the next few miles take you into Waynesboro and your lodging for the night. The city is a delightful combination of parks, specialty shops, restaurants and scenic surroundings.

Day 7

The ride back to Staunton is approximately 32 miles through the southern Shenandoah Valley. A perfect last day's ride to enjoy the rural tranquility of the area. Leaving Waynesboro center city the terrain is relatively level as you follow the baselines of the surrounding mountains. Your ride ends in Staunton at your lodging. After the day's ride you can relax by spending the evening at the Blackfriar's Playhouse and dining.

Day 8

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


  • The cost of the Extended Southern Shenandoah Valley Tour package as described is $1,720 per person/double occupancy and luggage transfers; the single supplement is $850.
  • This tour is rated moderately difficult because of long rides and rolling country roads with 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 breakfast each morning as provided by your lodging and three dinners. You will have arrival orientation, comprehensive route instructions, supporting maps, and emergency support.
  • This tour can be booked to start the first Sunday in May and to end by the last Friday in October and is generally scheduled to start Sunday evening and end Tuesday morning; however other start and end days are workable as well but during certain times of the season, particularly during the foliage season and on most weekends, room accommodations can be difficult and can carry a premium. With adequate lead time, these can often be overcome.