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Southern Shenandoah Bicycle Tour 
A bicycling vacation of the southern Shenandoah Valley, Allegheny Mountains, and Blue Ridge Mountains 

Day 1 l Day 2 l Day 3 l Day 4 l Day 5 l Lodging l Getting There l Cycling  

Breathtaking Blue Ridge overlooks, pastoral valley farms, and winding mountain passes provide the setting for this incredibly diverse tour.  Jagged Alleghenies on the west and the awesome Blue Ridge on the east define the boundaries of the fertile agricultural Shenandoah Valley.  Farm roads through the rolling valley, forest roads through the quiet George Washington National Forest, and the Blue Ridge Parkway along that famous ridge top provide some of the most beautiful bicycle routes you could ever hope to ride.  Nightly, relax in gracious inns -- one in a beautiful country setting, and two in downtown historic districts.

(***Note:  We are also offering a Northern Shenandoah Tour beginning and ending in Charlottesville, VA.  Click here for additional details).

Southern Shenandoah Tour Fast Facts:
Highlights: Dates: Price:

Spectacular road cycling, including miles on the famous Blue Ridge Parkway

Pastoral back roads of the Shenandoah Valley

A memorable inn in a pristine mountain setting

Charming Staunton, VA

5 days / 4 nights

2018 Dates:

May 7 - 11

Oct. t.b.a.

(All Dates are M - F)

Opt in for email date
announcements here:


2018 Tour Price:

$1,695 - 1,795 / person
Price range reflects early to late enrollment.  

Bike rental: $100
Single occupancy room supplement: $400

Tour prices subject to change

Dates with an asterisk * have a solo traveler hoping for a roommate--  Call for details
RESERVE YOUR SPOT (click here)  


We begin this tour in historic Staunton, VA, in the center of Shenandoah Valley. Home base is Frederick House, a five building inn in the heart of vibrant downtown Staunton.   Arrive a day early to explore Staunton’s five historic districts and Woodrow Wilson’s birthplace on foot. Schedule permitting, see a show at the acclaimed Shenandoah Shakespeare Blackfriars Playhouse -- an authentic recreation of the bard’s winter theater in London.

Day 1:  

Meet in Staunton ready to bike.  Today is a full day of biking the lovely valley farm roads and visiting small towns along the way. We'll visit Natural Chimneys, a formation of stone towers created by the collapse of an ancient cavern. We'll also bike through an area of Mennonite farms. Mennonites have been in the area since the 1720's. 

Bicycling Route, Inn to Inn:  30 - 75 miles, 761-1990 feet of climbing

Day 2:  

Rise early for breakfast for a big day of bicycling.  We'll head southeast and approach the looming Blue Ridge. Wind your way up a gap to the Blue Ridge Parkway and spectacular overlooks. After logging additional spectacular miles on the Blue Ridge Parkway to our final overlook, we'll descend for an exhilarating 5 miles off the Blue Ridge down to the valley floor, where we'll make our way to Lexington, Virginia.  You'll want to explore this enticing historic village on foot from our downtown lodging.  Walk a few blocks to the campus of Washington and Lee University and Lee Chapel.  

Bicycling Route, Inn to Inn:  67 miles, 3942 feet of climbing

Bike Goshen Pass to a Maury River overlook.Day 3:  

We pedal from town today from our hotel in Lexington.  In a few minutes, we pass the quaint downtown and both Washington and Lee University and VMI.  Moments later we are on a serene country road following a mountain stream.  Then we turn into the Allegheny mountains via breathtaking Goshen Pass.  This scenic route follows the Maury River to the small town of Goshen and into the George Washington National Forest of remote Bath County.  We arrive in the afternoon at our destination of Fort Lewis Lodge, with its renowned local cuisine and rustic farm setting.  Take a hike to the top of the mountain ridge for a spectacular view overlooking the expansive farm.  Cool off in the swimming hole at the Cowpasture River.  Or, loosen your muscles in the hot tub.  At dinner, you will discover why folks travel long distances just to dine at Fort Lewis on Caryl Cowden's contemporary southern cuisine.  Before bed, walk up to the star gazing deck for a “light-free” look at the Milky Way.  

Bicycling Route, Inn to Inn:  45 - 61 miles, 1827 - 2450 feet of climbing

Fort Lewis LodgeDay 4:  

Enjoy a Fort Lewis country breakfast, then hit the quiet back roads of the George Washington National Forest.  Our bikes normally outnumber cars during long sections of this day's route.  Cycling through this lightly populated region, you will enjoy beautiful views of mountain rivers and forests, and a couple of quiet mountain communities.  A few challenging climbs will punctuate the day's ramble.  You will be pleasantly exhausted by the time you arrive back at Fort Lewis Lodge for a second evening of serenity.  

Bicycling Route, Inn to Inn:  61 miles, 3380 feet of climbing

Day 5:  

Our final day takes us to more beautiful roads in the G. W. National Forest lead us to a mountain pass which returns us to the Shenandoah Valley, where final catered lunch and showers await, prior to departure. Extend your stay in Virginia to explore the southern high country or to venture northward into Shenandoah National Park.

Bicycling Route, Inn to Inn:  50 miles, 1581 feet of climbing


"We were so pleased with our first Carolina Tailwinds vacation. You seemed to have thought of everything.  The routes were just beautiful, the accommodations were great and the meals were excellent.  Everything about this tour was so well organized, from start to finish."
--  MaryAnn, Waterbury, CT



Optional Nights before or after tour and Night 1 :  Frederick House, is located a short walk from everything in historic downtown Staunton, Virginia, in the heart of the Shenandoah Valley.  Frederick House’s five 19th century residences offer 23 spacious rooms and suites in award winning-buildings. The buildings date from 1809.

Night 2:  Hampton Inn Col Alto, Lexington, VA.  No typical Hampton Inn, this facility incorporates a 1827 mansion and several acres of lovely shaded grounds.  Walking distance to historic downtown shops, restaurants, and museums of charming Lexington.

Nights 3 & 4: Fort Lewis Lodge, Millboro, VA.  Innkeepers John & Caryl Cowden welcome us to their historic farm in remote Bath County, VA.  Spacious rooms in the main lodge are furnished in a Shaker-style tradition. An attached glazed-tile silo has been renovated with a spiral staircase leading to three very private bedrooms-in-the-round.  There’s even a “lookout” on top for expansive views of rolling meadows and rugged cliffs towering above the river.



This tour is a roadie's dream, and is appropriate for intermediate or advanced bicyclists.  We recommend modern road bikes, preferably with triple chainrings or large rear cogs to tame the hills.  All biking is on asphalt roads except for a few very short sections of packed gravel.  Our routes bypass the most challenging climbs in the area, but there are very few flat sections.  Distance options each day range from 30 to 60 miles, with optional side routes available to add on miles.  Terrain is a mix of rolling hills and strenuous climbs.  The scenery is very beautiful and diverse, including valley farms, forested mountains, and the Blue Ridge Parkway.

"The laminated maps & directions (with supporting odometer) were very practical and useful. 
The generally rural, pastoral, low-traffic route was simply great."
-- Clint, Georgetown, SC


All meals are included, with the exception of one "on-your-own" dinner in Lexington, VA.  This includes substantial breakfasts, picnic lunches, gourmet dinners and abundant snacks and beverages.

Getting to the Tour Start (Staunton, VA):


Shenandoah Valley Regional Airport, Weyers Cave, VA,  540-234-8304,
SHD is 16 miles from downtown Staunton.  Local shuttle service available.
United offers flights to and from Washington-Dulles International Airport.

Charlottesville Albemarle Airport (CHO) is 54 miles away from Staunton. 
US Airways Express, United Express, Northwest Airlines, and Delta Connection provide non-stop service to six major connecting cities.

Roanoke-Blacksburg Regional Airport in Roanoke, VA is 83 miles, or approximately 1-1/2 hours away from Staunton.  
US Airways, United Express, Northwest Airlink, and the Delta Connection carriers, ASA and Comair provide non-stop service to eight major cities.

Ground Transportation:  Shuttle service is available at SHD.  Multiple shuttle and cab companies are available at CHO and ROA.  Multiple car rental agencies are available at each airport.  Carolina Tailwinds may be able to offer a complementary ground shuttle to/from the tour if you fly in and out of ROA.  Call us for more details.

Driving:  Staunton is located at the intersection of I-81 and I-64 east.  It is 108 miles from Richmond, 272 miles from Charlotte, and 293 miles from Philadelphia.

Timing:  We bike away from Staunton on the first morning of the tour.  Try to arrive in Staunton no later than 9 a.m., 8:45 a.m. if you are renting a bike from us.  Departure time from Staunton on the last day will be around 2 - 3 p.m.

Extend Your Stay in the Area:  Because Staunton is consistently listed by travel writers as one of the best small towns in American and one of the towns you should visit this year, you may want to linger longer.  Staunton is definitely one of our favorite small towns for its restaurants, museums and the American Shakespeare Center.  There is plenty of additional cycling and hiking to do in all directions.  Here are a few Staunton links to explore:




Carolina Tailwinds guides tours on the Blue Ridge Parkway under a Commercial Use Permit issued by the Blue Ridge Parkway National Park.

Carolina Tailwinds reserves the right to make alterations to the itinerary as needed.  Any changes made will maintain or enhance the quality of the tour.

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