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

Day 1

Arrive in Winchester and settle into your accommodations. On your schedule you will meet with your Virginia Bicycling Adventures representative to review your tour material. The City of Winchester was established in 1732 by settlers from Germany, Scotland and Ireland. Winchester played a role in every war based on American soil.  Winchester is where sixteen year old George Washing began his three career paths. During the Civil War, Winchester held such strategic importance that it changed hands 72 times and reportedly 13 times in single day. General Stonewall Jackson based his famous Valley Campaign in Winchester. During the War, Winchester was the site of six major engagements.

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***

After breakfast, on you own time schedule, you can venture off on the day's ride which will take you out of Winchester over city streets onto pleasant rural roads through Frederick, Clarke and Warren counties. Initially you will have spectacular views of the Blue Ridge Mountains and the northern end of the Valley with the second half following the shoreline of the Shenandoah River. 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 Virginia low water bridge. This is a very pleasant ride of approximately 54 miles.

*** For those riders seeking more of a challenge, the Extended Shenandoah Tour can follow a 62 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.

As an alternative or in addition to the ride over the Massanutten Mountain a challenging 62 mile ride over the Fetzer Gap in North Mountain can be scheduled. This ride 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 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 6.8 percent and four
switchbacks.

Each of these rides can be a substitution or an addition to your tour package. Both are difficult and only should be considered by those with advanced biking skills and experience.
 

Day 3

Day 4

Today's ride will take you out of Strasburg to Middletown where the Battle of Cedar Creek was waged and is annually re-enacted with more than 5,000 participants. You will pedal through the Village of Middletown with a history preceding the Revolutionary War and site of numerous skirmishes in the Valley campaigns of 1862 and 1864. Pedaling through the village you will pass antique shops, the Wayside Inn with a century’s old history and the town cemetery that was the Confederate high water mark at the Battle of Cedar Creek. You will continue over pleasant country roads through farms and battlefields where much of the Valley Campaign of 1864 was conducted. You can visit the areas where the battles of Toms Brook, Round Hill and Fishers Hill were fought with numerous opportunities to view the battlefields and surrounding landscape. Your return to Strasburg will pass the remains of the Tumbling Run Bridge which collapsed during the Confederate retreat from the Battle of Cedar Creek causing the abandonment of untold numbers of wagons and cannons. The ride is 42 miles and is in the moderate category.

Day 5

Your bike route today leaves Mount Jackson heading towards the Allegheny Mountains with a gradual climb into the foothills where you will be rewarded with spectacular views of the Valley and mountain ranges on both sides. Leaving the ridge, you will experience one of the reasons you climb hills as the down hill run into Timberville is long and fast.The remainder of the day's ride meanders along the North Fork of the Shenandoah River over typical Virginia rural roads with small rolling grades and very low traffic. You will end your ride going through the Meems Bottom Bridge which is the longest covered bridge in Virginia. This moderate ride is 36 miles.

Day 6

This ride leaves from your B&B in Harrisonburg and takes you through the center of the Shenandoah Valley along farmlands and over hills and ridges that provide spectacular views of the Allegheny and Blue Ridge Mountains. Initially, there are some climbs, none very steep but the terrain flattens out to very sparsely traveled country roads. An excellent detour of a few miles will take you into Natural Chimneys National Park. The chimneys are natural limestone towers reaching over 120 feet. Today's ride also offers the opportunity of a challenging 9 mile detour with 2.5 miles of climbing to Todd Lake in the George Washington National Forest. This is a moderate ride of 55 miles or 64, if the Todd Lake option is taken.

Day 7

Today's ride leaves from your lodging and takes you to the eastern reaches of the Shenandoah Valley as you bike over gently rolling roads to Waynesboro which is named after the Revolutionary War hero Mad Anthony Wayne. You leave Staunton on quiet city streets to bike several miles on scenic country roads and then enter Waynesboro through neighborhood streets passing the P. Buckley Moss Art Museum. Waynesboro is a small, quaint city with numerous specialty shops. Your ride now returns to pleasant country roads running along Calf Mountain and Ramsey Mountain following a mountain stream down to South River. Your route will pass though several quaint villages along rural country roads with spectacular views of the Blue Ridge Mountains. Coming around Fishersville you will begin your return to Staunton. This is an easy ride of 47 miles on gently rolling country roads.

Day 8

The last day's ride out of Lexington will take you over some of the most well-known bicycling roads in Rockbridge County. Your ride out of town passes a confederate cemetery then goes into the countryside. You will glide down virtually empty roads through awesome scenic hills and rolling country; making your way up a gradual ascent you will be rewarded with an 11 mile gradual downhill run that is pure relaxation and among the best experiences the southern end of the Shenandoah Valley has to offer. You will finish your ride into Lexington surrounded by two towering mountains and a last climb that will set you up for a two-mile decent into town. This ride is in the moderate category and covers 43 miles and will provide lasting memories of bicycling in the Shenandoah Valley.

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 $1,235 per person/double occupancy; the single supplement is $640. A non-B&B tour can be arranged with a cost of $852 per person/double occupancy; the single supplement is $425.
  
• 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, four lunches 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.