Self-Guided Tours
Extended Shenandoah Tour

Our Extended Northern Shenandoah Valley Bicycle Tour begins in Winchester and goes south through the Shenandoah Valley and back to your starting location in Winchester. You will bicycle over scenic country roads through rolling hills, farmlands, apple orchards and civil war battle sights, awesome mountain vistas and challenging climbs are just some of what you will experience each day on our extended tour through the northern Shenandoah Valley. This Self-Guided tour is rated moderate to difficult; although there are many flat stretches, several of the rides are long, most have stretches over country roads with rolling terrain and climbs, a few of which are steep.


Day 1

Arrive at your B&B in Winchester and meet with the Virginia Bicycling Adventures representative to review the tour details. Relax and contemplate the tour's rides or explore the town. It is a delightful place to simply stroll through the main historic street, the mall shops and to visit the restaurants or the surrounding historic neighborhood to view the period architecture. With numerous antique stores, several museums and many Civil War sites, such as Stonewall Jackson's headquarters. Established before the Revolutionary War and the site of four battles during the Civil War, Winchester has a long and deep history. Close the evening with a relaxing dinner.


Day 2***

A loop ride of 56 mile ride 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. Initially you will follow the Shenandoah River with the second half providing spectacular views of the Blue Ridge Mountains. This is a relaxing ride through the countryside that even offers opportunities to wade in the Shenandoah River which is shallow and near a low water bridge. This ride is over rolling roads with 3,300 feet of climb due more to length than steep climbs. 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.

*** For those riders seeking more of a challenge an alternative route out of Winchester available. It is a mountain crossing with 5,800 feet of climb.

The mountain crossing is a challenging 62 mile ride that begins with 30 miles over rolling rural roads with increasingly steeper sections as a prelude to the 1.9 mile climb up the mountain with an average of 7.7 percent grade. At 1883 feet of elevation the view of the Shenandoah Valley from the top is unobstructed. Take the time to savor it as there is no time to take in the view on the rapid decent back into the Valley with an average grade of 6.5 percent and four switchbacks.

This ride can be a substitution or an addition to your tour package. The mountain crossing is difficult and only should be considered by those with advanced biking skills and experience.

Day 3

The day's ride of 37 miles starts with a short ride through Winchester and then onto rolling country roads typical of the Shenandoah Valley. You will bike through Opequon, past apple orchards and onto roads virtually free of vehicles. Your route continues over pleasant country roads through farms and battlefields where much of the Civil War Valley Campaign of 1864 and Revolutionary War activities were conducted. Your lodging for the night is in Strasburg.

Established before the Revolutionary War and a hub of activity during the Civil War, Strasburg has a long and deep history that is evident in its ambiance. Close the evening with a relaxing dinner and a stroll past many historic homes.

Day 4

Strasburg to Woodstock is a 38 mile ride through Fort Valley and over the Massanutten Mountain into Edinburg then onto Woodstock where you will overnight. The 3 mile climb averages 6.6 percent with a maximum of 8 percent; the downhill is a technical challenge that averages 10 percent with a series of "S" curves. The remaining few miles to your lodging in Woodstock are on typical country roads found in the Valley.

Day 5

Today you bike south 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 then follow the North Fork of the Shenandoah River which you cross through the covered Meems Bottom Bridge then on into Mt Jackson. At ride's end you will be at the Widow Kip's Country Inn for your night's lodging and a relaxing afternoon.

Day 6

Today you bike 40 miles from Mt. Jackson to Strasburg. Your route will take you past a winery, through the Fishers Hill Battlefield, along the North Fork of the Shenandoah River into Strasburg where you will overnight.

Day 7

Today’s ride of 34 miles returns you to your starting location in Winchester and will pass the Cedar Creek Battlefield and Belle Grove Mansion into Middletown and then over generally different country roads than your first day’s ride from Winchester but with similar topography.

Day 8

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

  • The cost of the Extended Shenandoah Valley Tour package as described is $1,590 per person/double occupancy and luggage transfers; the single supplement is $700.
  • 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 seven full breakfasts 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 fall 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.