Don’t miss this thoughtfully planned, multi-day outdoor adventure in Virginia, cycling through the picturesque landscapes of the Southern Shenandoah region. Traverse rolling valleys, ascend winding mountain passes, and soak in the breathtaking views while you visit Virginia Blue Ridge’s majestic overlooks. Bike the heart of the valley, where the rugged Allegheny Mountains to the west and the awe-inspiring Blue Ridge Mountains to the east frame the fertile agricultural lands below. Pedal along peaceful farm roads, venture through the serene George Washington National Forest, and follow the iconic Blue Ridge Parkway atop the famous ridge line. Each day brings a new adventure, promising a blend of natural beauty and rural charm that defines the essence of this remarkable region.
Carolina Tailwinds, hands down, is the best bicycle touring company anywhere. Their attention to detail and willingness to accommodate personal preferences are unsurpassed. Their routes are well-planned and the support and ability to deal with different riding levels…My wife and I have done nine tours with Carolina Tailwinds…We are veteran cyclists; if their tours were not really good, we would have never returned…we are going on our tenth this year.
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Trip Overview
Price
Early bird discount: $2325 per person
Full price: $2425 per person
Bicycle rental : $100
Single room supplement: $500
Upcoming tour dates & status
For the 2025 season, no dates are currently scheduled. Groups of 8 or more are welcome to inquire about private or non-private options.
Meeting/Departure Point
Nearest Airport
SHD Shenandoah Valley Regional
Duration
5 days, 4 nights
Tour difficulty
Hilly with challenging climbs
Included
- Lodging:
4 nights at unique country inns and downtown
hotels. - Meals:
Dinner on nights 1, 3 & 4; all lunches; all breakfasts; snacks; and hors d’oeuvres most nights. - 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.
Group Size
Carolina Tailwinds maintains a guest to guide maximum ratio of 7:1 on all our tours
About your guide
Expert guides ready to show you the hidden wonders of each and every destination
What You’ll See & Do
Day 1
31–75 miles, hilly with a several short 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
BRP 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.
Alternate Itinerary on Rainy or Foggy Days:
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 couple of challenging climbs will punctuate the day’s ramble. (Van shuttle past those if you prefer.) 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 short 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 in Staunton, a final lunch awaits prior to departure. Extend your stay in Virginia to explore the southern high country or to venture northward into Shenandoah National Park.
What’s Included in Your Tour Price?
Tour prices are per person rates and include all of the following:
- Lodging costs (double occupancy rooms), including all taxes and fees
- All breakfasts and most lunches
- All dinners described in the tour itinerary (alcoholic beverages in restaurants are generally not included)
- Morning and afternoon snacks
- Route planning and detailed laminated cue cards daily
- Guide support along the route
- Van support along the route
- Luggage transfer
- Fees for all ferries, 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
- Carolina Tailwinds t-shirt or day bag, water bottles, complimentary digital photo files from your tour
- Gratuities for restaurants at included meals and gratuities for housekeepers at included lodging
Please note:
All lodging costs are based on double occupancy. The single room surcharge rates apply to single room occupants.
Single travelers who desire a roommate match will be paired with other tour guests of the same gender in a room with two beds, if available. If a match can’t be found for a single traveler, a single occupancy surcharge will be assessed. To find out if a roommate match is available, call us. We will be happy to put you on a waitlist for a match if one is not already available.
Single travelers may request a private room, subject to availability, and to the single room surcharge rate payable in full at the time of the reservation.
Transportation to the tour starting point, including airfare and any airport transfers, is not included in the tour price. We can assist you with making any airport transportation arrangements or advise you on the nearest and most convenient airport.
Alcoholic beverages at restaurants are not generally included . A separate beverage tab may be run for anyone who would like a drink with dinner. Settling this tab will be the responsibility of the individual participants.
Bicycle rental is available as an option (prices above). We have road touring bikes and hybrid bikes for your use and invite you to forego the hassle of transporting your bike to and from the starting point. Click here for more information on the equipment available for your use.
Want to know more about our policies, terms and conditions? Click here to review our deposit requirements, cancellation policy and more.
We will be happy to address any additional concerns or questions you may have.
Simply email us at our Contact Us page, or call us at 1-888-251-3206 (local number is 336.794.1054). Ready to make your reservation? Click here to reserve a spot online, or call us at 1-888-251-3206 (local number is 336.794.1054).
Travel Insurance: We strongly encourage you to consider travel insurance. You may research and compare competing travel insurance policies at websites such as www.squaremouth.com.
Where You’ll Be Staying
Night 1
Hotel 24 South
Located in the middle of historic downtown Staunton, Virginia, in the heart of the Shenandoah Valley. This historic hotel was constructed in 1924 and retains the beauty and charm of its original architecture, while offering all of the amenities and standards of a modern hotel.
Night 2
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.
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.
Get Prepared!
Cycling
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
Hotel 24 South, 24 South Market Street, Staunton, Virginia 24401.
Getting to the Tour Start (Beaufort, NC):
Driving: Approximate travel distance to Stanton–
- 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
American, 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
American, 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 that location.
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 America 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.
Rental Bikes for Your Tour
Our Selection
Women’s Road Bike ⇒
⇐ Men’s Road Bike
Hybrid Bike Small ⇒
⇐ Hybrid Bike Large
Step Through Bike ⇒
Why Choose This Tour?
Pedal through picturesque valley farm roads and visit Natural Chimneys, a stunning formation of stone towers
Conquer challenging climbs and enjoy breathtaking overlooks on the Blue Ridge Parkway
Explore historic Lexington, including Washington and Lee University and University Chapel
Experience serene country roads and majestic mountain scenery in remote and rural Bath County
Conclude with a scenic ride through the G. W. National Forest, culminating in a memorable mountain pass descent back to the Shenandoah Valley
See What Our Customers Say About Us
We just signed up for our third tour with this excellent bike tour company. We fly from California just to go with Carolina Tailwinds. Their attention to every small detail is amazing. I think their personal attention as owners of the company is what makes the difference…really do care that each of their customers has the best possible biking vacation.
…The routes afforded beautiful scenery, and were well-supported…We especially liked the personal touch that Anne and Greg provided. They picked us up at our hotel; they kept a watchful eye on rider groups with a broad range of skills; and they hosted informal drinks and hors d’oeuvres each night before dinner…great exercise during the day and relaxing evenings with interesting people, comfortable lodging, and excellent meals.
Aside from knowing some of the most unique biking, lodging, and dining spots in the Mid-Atlantic area, Anne and Greg obviously love what they are doing…This husband and wife team is really tops when it comes to personal, friendly service and they excel in accommodating the needs of riders of all abilities…Our only complaint is that we never seem to lose any weight on their tours, but as they always remind us – “It’s a vacation, you’re not supposed to lose weight!” Looking forward to our fourth trip in four years with Carolina Tailwinds!
Trips are well planned and very well supported. The lodging chosen by the company suits the trips, are comfortable, and often unique. But the most notable item is the personal attention a rider receives throughout the trip. I’ve completed three trips with Carolina Tailwinds and have signed up for a fourth.
…‘Company’ is misleading: this is a personal experience…Count on excellent routing, craft-quality laminated and color-coded cue sheets, a daily pre-ride briefing, convenient and dependable sag support, and smaller, friendly groups. The clinchers for me, though, were the gourmet meals and the accommodations at small inns…I’ve been on 3 different trips with them now, and all cycling agendas have been represented and handled on each trip.
We love this company. We have toured with them three, going on four times and their attention to every detail and their organization skills keep us coming back for more. we have toured with three other companies, vbt, bike vermont, and pedal and sea adventures, and they surpass all of them. Food especially is excellent.
Carolina Tailwinds gives every attention to detail towards their customers. The routes they map out are clear and safe. The accommodations that Carolina Tailwinds select are 5 star all the way, from the lodging to the restaurants. The guides are friendly and accommodating to the cycling level of their guests. The size of the tour group are intentionally small to give the customer that undivided attention they deserve on their vacation.
We had used several bike tour companies and thought that they all did a good job. However, Carolina Tailwinds’ tours are operated by the owners of the company. Thus, their level of service exceeds that of other companies. We have now completed 5 tours with them and have another scheduled. Greg and Anne, the owners, are now like members of our family.
We are in our mid-seventies & have just re-discovered the joys of biking the past 3 years, biking over 2500 miles each of the last 2 seasons mostly hear in upstate NY. We’ve started the past 2 seasons with a Carolina Tailwinds tour & plan to do the same again this season. Anne & Greg just do a terrific job guaranteeing a wonderful vacation for us.
We did the Florida tour with a group of 16. The inns selected by Anne and Greg were a pleasant surprise as were the restaurants. Steve’s patience and guidance while biking was greatly appreciated. We have toured together before but this was the most supported experience we have had. Their bikes were excellent. I highly recommend scheduling with this company.
Tailwinds offers routes that can vary from easy to challenging, but that are always scenic and engaging. The support on the road is absolutely best in class, the lodgings are always interesting, and the food is terrific. Best of all, the owners and guides personify “customer service.” Taking a Tailwinds tour is always the highlight of my cycling year. All of this at prices which are reasonable.
We just got back from a fantastic vacation with Carolina Tailwinds. They were super accommodating and fun. The trip had good variety including cycling, two boat rides, beach walk, kayaking, amazing food and happy hour every day. Every expectation was exceeded as they booked a private tour for my husband’s birthday bash. Equipment was fantastic and the guides were personal me and knowledgeable. Booking was easy and every detail was take. Care of. Thank you to the whole team.
We are two retired friends who left our non-cycling husbands at home to have a biking adventure. We throughly enjoyed our Florida tour…Anne and Greg attending to every detail…Although it seemed we were on our own, our guides were at our backs to provide snacks, sun screen, and any assistance needed…The bikers we rented from CT were fitted to us and were maintained in perfect condition…FIRST RATE! We’re ready to book another CT trip!
We have completed 4 trips with Anne and Greg and have another on reservation. Their attention to detail is evident throughout the tour but especially in the excellent route selection. Good riding is of course why most people go on a bike tour and we have never been disappointed with the miles they carefully select. Good food, nice accommodations, interesting off bike activities and leisurely happy hours all adds up to a relaxing vacation.
This company is awesome! I’ve been on several week long tours and this is by far the best company. My husband and I just completed our second tour with CT and every aspect was first class. The guides are attentive no matter what your skill level. We’re planning a third trip next year.!
…Having been on several other bike companies’ tours I have a good perspective to highly recommend Carolina Tailwinds…They were perfectly organized, personally knowledgeable of the routes, and prepared for everything we wanted or needed for a great week…All through the week CT added fine touches to our trip which you’ll just have to experience on your own CT tour. You’ll have an awesome week.
Excellent value. Routes, accommodations, food, activities, support, and equipment were all top notch. Superb attention to details big and small. I have toured with nearly a dozen companies. They were all good, but Carolina Tailwinds has been my favorite. You can spend more, but you won’t get more than you get from Anne and Greg.
The attention to detail and the readiness to accomodate requests from the riders separate Carolina Tailwinds from any other tour group that I have ridden with. One other feature that has to be mentioned is the standard of the accomodations and the food. They are both of the highest standard. The Carolina Tailwind tours are fun!
…The scenery was abolutely spectacular! Traffic was light and road conditions excellent. The routes were well-planned with detailed cue sheets that were easy to follow. The support we received from the CT team was first rate before, during and after each day’s ride. Accomodations were very good if not top of the line. The tour operators, Anne and Greg, are well-organized, friendly, and good companions on a ride. We will be repeat customers this Summer.
