Day by Day Itinerary

Southern Shenandoah Tour 2015

Countries   USA
Tour Length   5 days
Dates Of Tour   Monday, May 11, 2015
Monday, September 7, 2015
Type of Tour Road (Guided)
Price $1,695 ($ 1595 if paid in full by 180 days from tour start date.)
Family Friendly
Age of Participants Mixed
Gender Basis Mixed
# of Participants (max) 18
Language English
Sleeping Accommodations   
Luggage Support
Sag Wagon Along the Way
Meals Provided Full board
Total Trip Mileage    275 Miles
Average Daily Mileage    55 Miles Per Day
Longest Single Day 60 Miles
Total Trip Altitude Gain +17000 ft
Single Day Altitude Gain   +3400 ft
Overall Difficulty Rating   Intermediate
Cost of Trip without Airfare per person  $1,525
Single Supplement $375
  • Lodging costs (double occupancy rooms), including all taxes and fees
  • All meals with the exception of one dinner "on your own."
  • Morning and afternoon snacks
  • Route planning and detailed daily area maps
  • Guide support along the route
  • Van support along the route
  • Luggage transfer
  • Tolls for all highways and any park entrance or guided tour fees where noted
  • Transportation back to starting point
  • Costs for any special activities such as canoeing, kayaking, sailing or rafting
  • where noted
  • Complimentary online photos of your tour, Carolina Tailwinds t-shirt, and water bottles
  • Historic Downtown Lexington, VA -- home of Washington & Lee University and Lee Chapel.
  • Fort Lewis Lodge -- A gracious country inn secluded deep in George Washington National Forest.
  • Natural Chimneys -- visit a mysterious rock formation in the heart of the Shenandoah Valley.
  • Historic Downtown Staunton, VA -- includes five walkable historic districts, and Blackfriars Playhouse, the world's only re-creation of Shakespeare's original indoor theatre.
  • The Blue Ridge Parkway -- bike up to, along, and down from one of the most beautiful stretches of the great byway.

Five full days of bicycling bring you breathtaking Blue Ridge overlooks, pastoral valley farm roads, and winding mountain passes provide the setting for this incredibly diverse tour. Beautiful southern Shenandoah Valley is at the center of this journey. With the Alleghenies to the west and the Blue Ridge to the east, Shenandoah Valley has long been a fertile agricultural area, and remains so today. Farm roads meander through the valley, following the rolling contours of the land. Grapevines occasionally dot the landscape as do several Civil War historical sites. Nightly, relax in gracious inns -- two in beautiful country settings, and one in a downtown historic district.

Day 1   Shenandoah Valley loop ride from Staunton
Day 2   Bike the Blue Ridge Parkway
Day 3   Bike Goshen Pass into the Allegheny Mountains
Day 4   Explore Bath County, Virginia
Day 5   Bicycle hidden valley roads
Additional Activities During Trip
Optional hikes, downtown shopping, natural & historical exhibits
Countries Visited  
  • USA
    • Virginia
Cities Visited   Lexington, Millboro, Staunton
Early Bird Discounts

Enroll and pay in full 180 days prior to your tour and receive a $100 discount off the tour price.

Enroll and pay in full 120 days prior to your tour and receive a $50 discount off the tour price.


• Optional Nights before or after tour, and
• Night 1: Frederick House, Staunton, VA is 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.

• Night 2: Hampton Inn Col Alto, Lexington, VA. Not a typical Hampton Inn! With all of the conveniences of a typical Hampton, this one is located in downtown Lexington and incorporates a 1827 mansion and its beautiful grounds into the facility. Walking distance to historic downtown shops, restaurants, and museums.

• 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 appropriate for intermediate or advanced bicyclists. We recommend modern road bikes, preferably with triple chainrings or large rear cogs. 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.


We have a new fleet of carbon bikes featuring Shimano components. We also carry a fleet of Fuji Absolute 1 Hybrid bikes suitable for road touring. You are welcome to bring your own saddle and pedals for us to install on our rental bike for you.

Company Name Carolina Tailwinds
Country     USA
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