Ride Virginia’s Blue Ridge on this unforgettable cycling adventure. Immerse yourself in breathtaking views at every turn as you cycle the Blue Ridge Parkway. From the vibrant energy of Virginia Tech in Blacksburg to the eclectic arts scene of Floyd, this tour offers a perfect blend of outdoor adventure, cultural exploration, and historic charm.
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.!
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Trip Overview
Price
Early bird discount: $2250 per person
Full price: $2450 per person
Bicycle rental : $100
Single room supplement: $375
Upcoming tour dates & status
No dates are scheduled for the 2025 tour season. Groups of 8 or more are welcome to inquire about private or non-private options.
Meeting/Departure Point
Nearest Airport
ROA Roanoke Blacksburg Regional
Duration
5 days, 4 nights
Tour difficulty
Hilly terrain, with some challenging climbs
Included
- Lodging:
4 Nights of Lodging, - Meals:
Dinner on nights 1, 2 & 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 Transportation from Roanoke Airport:
Carolina Tailwinds picks up on the morning of Day 1 and drops off in the late afternoon on Day 6 at the Roanoke Airport (ROA). Timing formally coordinated 2 weeks prior to the tour date.
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
25–35 miles, challenging climbs
Meet us at historic Hotel Roanoke downtown. Arrive early to explore this evolving railroad hub. (See below for things to do in the area) We’ll take a warm-up ride this afternoon to explore the nearby hills, including Mill Mountain, home to Roanoke’s iconic star. From the top, take in a sweeping view of downtown Roanoke, the vast railroad yards, and the surrounding mountains. Dinner will be included at an excellent restaurant downtown.
Day 2
49–71 miles, hilly with a few challenging climbs
After a delicious full buffet breakfast, we’ll take a brief shuttle to get away from city traffic and into the hills north of town. Our ride will take advantage of magnificent roads that wind between mountain ridges on their way to Blacksburg. We’ll arrive there for a late lunch and time to explore the campus of Virginia Tech. The town and campus are both bicycle and pedestrian friendly, so you will want to explore.
Blacksburg’s downtown shops and the nearby Smithfield Plantation are highlights. Smithfield is the meticulously restored 1774 home and gardens of Colonel William Preston and his descendants. Nearby is the Drillfield, the enormous central green space of the VT campus. On the Drillfield you will find the War Memorial Chapel and the April 16 memorial, honoring the memory of those lost in the tragic shooting of 2007. Surrounding the Drillfield on all sides are buildings of neo-gothic architecture clad in local limestone, known here as “Hokie Stone.”
Day 3
39–77 miles, hilly with some challenging climbs
Today we say goodbye to Blacksburg and head south to Floyd County. We’ll end up in the funky, artsy community of Floyd. Famous for live Bluegrass and roots music concerts, Floyd has attracted a cluster of artists and others looking for a small town with culture. Floyd residents are happy that there is only one stoplight in the entire county!
Day 4
47–72 miles, hilly with some challenging climbs
Today is a big day on the Blue Ridge Parkway, so get ready for some spectacular scenery and biking!
We have scheduled a stop today at Mabry Mill, one of the most photographed spots on the Blue Ridge Parkway. This site is popular for good reason – the tour of the mill is fascinating and they still grind cornmeal and buckwheat flour on site. We encourage you to stop and browse the mill and surrounding buildings providing a glimpse into life in rural Virginia in the early 1900’s.
You may also want to budget some time to explore Chateau Morrisette in the early afternoon. The vineyard and winery sits just off the Parkway and tastings are available for those who are interested.
Lastly, you may want to have some free time today to continue to explore the quiet and quaint downtown of Floyd. Many shops and restaurants are located within a few blocks of our inn. The late afternoon is also an opportunity to schedule a massage with a local therapist located within walking distance of our inn
Day 5
40–50 miles, hilly, with some big descents
It’s time to make our way back to Roanoke. The Blue Ridge Parkway will provide the longest segment of the journey, including a spectacular sustained descent from Bent Mountain. Begun as a works project in 1935, the BRP is a 470 mile scenic drive stretching from Shenandoah National Park to the Great Smoky Mountains National Park. The section that we will enjoy on this day has the characteristic small farms and meadows, split rail fences and occasional overlooks. Just outside of Roanoke, we’ll descend from the Parkway into Roanoke Valley. We’ll wrap things up with a final lunch back at the hotel. As with all of our tours, showers are available prior to departure.
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 Roanoke
Built by the Norfolk Southern Railroad in 1882, this grand facility was renovated by the city and Virginia Tech in the 1990’s, and is now under Hilton’s Curio brand. Connected to shops, restaurants and museums by a pedestrian bridge, this is the location for exploring downtown Roanoke.
Night 2
Inn at Virginia Tech
Located on campus, walking distance from Blacksburg’s Main Street, this modern facility is built of the “Hokie Stone” that is a hallmark of Virginia Tech buildings. Preston’s Restaurant on site provides an excellent breakfast buffet in the morning.
Nights 3 & 4
Hotel Floyd
In the heart of offbeat downtown Floyd, it’s a short stroll to shops, restaurants, and the famous Floyd Country Store. The hotel is committed to eco-friendly construction materials, soaps, and technologies. Each room is decorated with local handmade furniture and art, and is equipped with high definition television and wi-fi.
Get Prepared!
Cycling
We will be in the Blue Ridge Mountains, the terrain is very hilly. Daily route distances described above are approximate, and options for more and less are always available.
As with all of our tours, less ambitious cyclists can take advantage of short cuts and strategic “leapfrog” van shuttles along the route to tailor the route to their needs.
Tour Point of Origin
Hotel Roanoke, 110 Shenandoah Avenue Roanoke, VA (540) 985-5900
Getting to the Tour Start (Roanoke, VA):
Driving: Approximate travel distance to Roanoke–
- Charlotte, NC: 195 miles
- Cincinnati, OH: 380 miles
- Nashville, TN: 439 miles
- Harrisburg, PA: 295 miles
- Washington DC: 240 miles
Airports:
Roanoke Regional Airport (ROA) offers more than 50 scheduled flights daily, providing nonstop service from Roanoke, Virginia to nine major cities. The major airlines that fly daily include Allegiant, American, United Airlines and Delta. Allegiant Air also provides full sized jets and frequent service to Florida. The airport is just minutes from hotel Roanoke. www.roanokeairport.com
Ground Transit:
A complimentary Hotel Roanoke shuttle is available for the seven minute ride between the airport and the hotel.
Parking: We have arranged for long term parking there 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
Arrival time of the first day of the tour is 12:00 noon if renting equipment from us, or 1:00 p.m. if bringing your own bike. Guests will want to meet us at these times dressed in bike clothes, or ready to change into them.
We plan to wrap up around 3:00 p.m. on the final day. Your return flight should be no earlier than 5:00 p.m. that evening.
Extend Your Vacation
Before or after our activity packed tour, you may want to tack on a few days. There is a lot to do in and around Roanoke if you have time.
Downtown Roanoke is home to these excellent attractions:
Taubman Museum of Art: Modern and contemporary art from around the world is featured, as well as regional art and touring exhibits.
O. Winston Link Museum: Housed in a restored, Loewy-designed railway passenger station, the museum exhibits the largest collection of Link’s photographs of 1950’s life along the N&W railroad.
History Museum of Western Virginia: Exhibits show history of the region — Native American, photography, military, folk-life. Location in downtown’s historic marketplace.
Virginia Museum of Transportation: Explore historic locomotives, cabooses and other rail equipment; antique automobiles, trucks and buses; and the new Wings over Virginia Aviation Gallery.
Hiking and Mountain Biking:
Carvins Cove Natural Reserve, just north of town, is the nation’s second largest municipal park, and is home to 40 miles of mountain bike trails.
The Appalachian Trail hiking trail passes by Roanoke. McAfee Knob offers panoramic views of the region.
Bedford, VA, 29 miles east is home to:
National D-Day Memorial: Bedford VA suffered the highest per capita D-Day losses in the nation. The National D-Day Memorial honors the Allied forces with stylized English Garden, haunting invasion tableau, and striking Victory Plaza.
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?
Begin your journey with a warm-up ride to Mill Mountain filled with panoramic views of downtown Roanoke and the surrounding mountains
Discover the vibrant town of Blacksburg, where you can explore the campus and downtown shops
Cycle through the scenic hills to reach Floyd County, known for its vibrant arts community, live Bluegrass music, eclectic shops and galleries
Stop at Mabry Mill, one of the most photographed spots on the Blue Ridge Parkway, to witness its historic mill
Conclude your journey with a thrilling descent along the Blue Ridge Parkway, offering breathtaking vistas of small farms, meadows, and the Roanoke Valley
See What Our Customers Say About Us
…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.
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.
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.
