Extended Shenandoah Valley Bicycle Tour Package Virginia Bicycling Adventures

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.

The itinerary of this tour can be changed to end the tour in Harrisonburg rather than returning to your starting location in Winchester.

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 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, the site for four battles during the Civil War, Winchester has a long and deep history. Close the evening with a relaxing dinner.

The Confederate National Cemetery in Winchester contains the remains of 7,500 Union and Confederate soldiers and officers, as well as governors, patriots and citizens from every age. Some historic sights to visit are Abram’s Delight Museum, Christ Episcopal Church, the Museum of the Shenandoah, George Washington’s Office Museum, Stonewall Jackson’s Headquarters, Old Courthouse Civil War Museum and Old Town Winchester.

Day 2***

A loop ride from Winchester 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. 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 two alternative routes out of Winchester are available. Each is about 58 miles in length; one is a mountain crossing with 5,800 feet of climb while the other is over rolling roads with 3,300 feet of climb due more to length than steep climbs.

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.

The other is a 52 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 south side of the river which is shallow and near a low water, one lane bridge. This ride provides is over rolling roads with 3,300 feet of climb due more to length than steep climbs.

Each of these rides 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 30 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****

This ride is approximately 36 miles from Strasburg to Woodstock through the Shenandoah Valley between the Massanutten Mountain and the Allegheny Mountains. You will pedal through pleasant countryside with views of both the Allegheny Mountains to the west and the Blue Ridge Mountains to the east. The route starts with a short steep ascent and then levels out to rolling country roads typical of the Shenandoah Valley. Along the way you will have several opportunities to visit local wineries. Coming into Woodstock, you will have time to visit the local shops. Your route continues the remaining few miles to your B&B for the night.

****For those riders seeking more of a challenge, the Extended Northern Shenandoah Tour can follow a 59 mile route along the east side of the Massanutten Mountain that brings you into Edinburg from the east over the mountain. 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 ride is difficult and only should be considered by those with advanced biking skills and experience.

Day 5

Today 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. Your return will pass several wineries over typical Virginia rural roads with small rolling grades and very low traffic back to Woodstock.

Day 6

Today you bike 35 miles from Woodstock to Middletown. Your route will take you past a winery, through the Fishers Hill Battlefield, along the North Fork of the Shenandoah, and past the Cedar Creek Battlefield and Belle Grove Mansion into Middletown where you will overnight.

Day 7

Today’s ride of 33 miles returns you to your starting location in Winchester over generally different 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.

Day 9 Tuesday Depart

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

The cost of the Extended Shenandoah Valley Tour package as described is $1,337 per person/double occupancy and luggage transfers; the single supplement is $710. A non-B&B tour can be arranged with a cost of $1,058 per person/double occupancy; the single supplement is $475.
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 nine full breakfasts, one lunch and three 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 Tuesday 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.