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Bike tour of Virginia's Allegheny & Blue Ridge Mountains and the Great Valley Between

A Spectacular 5 Day Cycling Tour of SW Virginia

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.

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Southern Shenandoah

Staunton, Lexington & Bath County, VA

Tour Difficulty

Hilly with Challenging Climbs


5 Days, 4 Nights


Frederick House, Staunton, VA

Nearest Airport

SHD Shenandoah Valley Regional


From $1995 per person


5/9/22 - 5/13/22 9/19/22 - 9/23/22
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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

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Day 1

31–75 miles, hilly with a few challenging climbs

Meet in Staunton ready to bike.  Today is a full day of biking the lovely valley farm roads and passing through a few crossroad communities along the way.  We'll visit Natural Chimneys, a formation of stone towers created by the collapse of an ancient cavern, where you will enjoy a catered picnic.  We'll also bike through an area of Mennonite farms. Mennonites have been in the area since the 1720's.   Return to Staunton in time to grab a quick post ride ice cream.  We'll enjoy dinner as a group a couple of blocks away at a local favorite.

Day 2

50–74 miles, challenging climbs

May Itinerary:

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.  

October Itinerary: Our route from Staunton to Lexington will use a spectacular valley route instead of the Blue Ridge Parkway. The 40 mile valley route will still include plenty of climbing and descending, and there is an optional 30 mile loop that can be added on after reaching Lexington. It is a great day on a bike either way!

Day 3

45–61 miles, hilly

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.  

Day 4

30–61 miles, hilly, with a few challenging climbs

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.  

Day 5

36–50 miles, hilly, with a few challenging climbs

Our final day takes us to more beautiful roads in the G. W. National Forest, leading us to a mountain pass which returns us to the Shenandoah Valley.   Back at Frederick House, a 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.


$1,995 - $2,095
Bike Rental
Single Room Supplement

2021 pricing shown will be honored on 2022 reservations indefinitely.  Price subject to change at any time.

Low end of tour price range reflects the 6 month Early Bird Discount.  High end of price range reflects no Early Bird Discount. 

What's Included in Your Tour Price


4 nights at unique country inns and downtown hotels


Dinner on Nights 1, 3 & 4; All lunches; All breakfasts; snacks; and hors d'oeuvres most nights.

Services of Expert Guides

Carolina Tailwinds maintains a guest to guide maximum ratio of 7:1 on all our tours.  Guides are ready to show you the hidden wonders of each and every destination.

Full Route Support & Luggage Transfer

Service of 1 – 2 support vans on route every day.

Complimentary Airport Transportation from Roanoke

Carolina Tailwinds may be able to offer a complementary ground shuttle to/from the tour if you fly in and out of Roanoke (ROA).  Call us for more details

More details on what's included: 

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Frederick House, Staunton, VA

Night 1

Frederick House

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.

Hampton Inn Col Alto, Lexington, VA

Night 2

Hampton Inn Col Alto:

Not a 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.

Fort Lewis Lodge, Bath County, VA

Nights 3 & 4

Fort Lewis Lodge

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.

Tour Point of Origin:

Frederick House, 28 N New St, Staunton, VA   (540) 885-4220

Getting to the Tour Start (Staunton, VA)

Driving:  Approximate travel distance to Staunton--

  • Richmond, VA:  108 miles
  • Washington, DC:  158 miles
  • Philadelphia, PA:  293 miles
  • Charlotte, NC:  272 miles
  • Cincinnati, OH:  414 miles

Airports: Shenandoah Valley Regional Airport, Weyers Cave, VA,  540-234-8304, www.flyshd.com
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.  www.gocho.com 
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.    www.roanokeairport.com  
US Airways, United Express, Northwest Airlink, and the Delta Connection carriers, ASA and Comair provide non-stop service to eight major cities.

Ground Transit: Local for hire 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.

Parking: We have arranged for complimentary long term parking for the duration of your tour.  We will end the tour at the same inn with an opportunity to shower there prior to departure.

Arrival/Departure 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 Vacation

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:



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Virginia Blue Ridge

Come ride the Blue Ridge Mountains.  Southwestern Virginia is home to beautiful sections of the Blue Ridge Parkway, the charming arts community of Floyd, bustling Blacksburg and mile after mile of beautiful road cycling.

This itinerary is great for the cyclist who doesn't care for van shuttles.  There is only one short shuttle built into the itinerary.  Otherwise, bike inn-to-inn each day!

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