Middle Tennessee beckons with its rural wonders, offering cyclists a journey through charming country landscapes and fun yet challenging hills. This six-day cycling adventure invites riders to explore the heart of the Volunteer State, where the rolling foothills and tranquil back roads reveal hidden treasures beyond the region’s famed music and spirits.
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: $2725 per person
Full price: $2825 per person
Bicycle rental : $100
Single room supplement: $600
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
BNA Nashville International Airport
Duration
6 days, 5 nights
Tour difficulty
Rolling terrain, with a few challenging climbs
Included
- Lodging:
5 nights at boutique inns. - Meals:
Dinner on nights 1, 3, 4 & 5; 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 Nashville:
Carolina Tailwinds picks up on the morning of day 1 and drops off in the late afternoon on day 6 at the Nashville Airport area, Opryland, and downtown Nashville inn locations to and from our tour start in Murfreesboro, TN. 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
40–45 miles, hilly terrain
Historic Murfreesboro’s charming downtown provides a dose of Americana and a hospitable start to our tour. We’ll meet midday in time to enjoy a quick spin ride in the beautiful surrounding countryside before dining as a group tonight.
Murfreesboro was also the site of one of the bloodiest conflicts of the Civil War. The Battle of Stones River began on the last day of 1862 and neither side was ever credited with an outright victory. However, the Confederate retreat in its wake was a strategic victory for the Union Army as Murfreesboro became a major supply depot for the Union troops and served to split the Confederate Army east to west. Today, the battlefield site is a place of peace and tranquility, with bicycle trails running through it.
Day 2
40–65 miles, hilly terrain
After breakfast, we venture to the lovely countryside of Coffee County. Thirty miles of rolling terrain will take us to our picnic lunch within the grounds of Old Stone Fort State Park. This 3 – 5 foot expansive falls is one of the most photographed sites in Middle Tennessee. Take a few minutes to explore the waterfalls and walk the easy trail of this Archaeological Park thought to be the site of a 2000 year old ceremonial ground for Native Americans. After lunch, continue pedaling to the big climb of the day — up to the Cumberland Plateau. Once on top, you will find the small town of Monteagle and the Monteagle Inn, our gracious home for two nights.
Day 3
25–50 miles, hilly terrain
Today, we will explore Suwanee and the gothic campus of the University of the South before our exciting descent off of the Cumberland Plateau. Country roads take us by Tims Ford Lake and over to Lynchburg, TN. It’s famous for one thing: the Jack Daniels Distillery. Ironically, the highest selling American whiskey in the world is manufactured in a dry county. That doesn’t seem to be a problem, as Moore County and its major employer get along just fine. We’ll tour the distillery and visitor center before lunch. After a bite in charming Lynchburg, we’ll roll back up to Monteagle (climb optional). We’ll savor a hearty dinner together with maybe a sample or two from today’s excursion!
Day 4
45–60 miles, hilly terrain
Saying a reluctant goodbye to our resort at Monteagle, we’ll make our way north toward Smithville. Along the way, we pass by the “Nursery Capital of the World,” the small town of McMinnville, TN, home to over 450 plant nurseries. Our destination is Evins Mill Retreat near the small town of Smithville. The site has seen several mills dating back to 1824. The last one was built in 1937 by State Senator Edgar Evins, whose son Joe L. Evins later became a powerful and long serving U.S. Congressman. The property has evolved after changing hands a few times into a beautiful lodge and conference center. An Evins Mill gourmet dinner will complete the day.
Day 5
45–60 miles, hilly terrain
We will explore features of the Upper Cumberland area today known for its many waterfalls, caverns and Center Hill Dam. Numerous scenic overlooks on today’s route provide some of the best views along the Eastern Highland Rim. Enjoy a picnic lunch overlooking Center Hill Lake before pedaling back to Evins Mill for another night surrounded by crickets and a babbling creek.We will dine together to recount the day’s activities.
Day 6
40–45 miles, hilly terrain
Our bike ride returns us to Murfreesboro through hilly valleys full of pastoral scenery on shady, lightly traveled roads. We’ll enjoy a long, gradual descent off the Highland Rim into the Central Basin of Tennessee, which includes Nashville and surrounding communities. Back in Murfreesboro, lunch and 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
Hilton Garden Inn, Murfreesboro, TN. Historic sites, public greenways, antiques, shopping, & restaurants are within a short distance, and downtown Nashville is a 40 minute drive.
Nights 2 & 3
Monteagle Inn & Retreat Center, Monteagle, TN. Located on the town’s main street and situated atop the Cumberland Plateau. A Select Registry Inn.
Nights 4 & 5
The Inn at Evins Mill, Smithville, TN. Nestled among the forested bluffs and meandering streams of Tennessee’s Highland Rim and Cumberland Plateau, Evins Mill is an inspiring resort destination.
Get Prepared!
Cycling
The terrain is a combination of gently rolling terrain, hills, and, in a few spots, challenging climbs.
As with all of our tours, less ambitious cyclists can take advantage of short cuts and strategic “leap frog” van shuttles along the route to tailor the route to their needs.
Tour Point of Origin
Hilton Garden Inn, 1335 Conference Center Blvd, Murfreesboro, TN (615) 225-2345.
Getting to the Tour Start (Murfreesboro, TN):
Driving: Approximate travel distance to Murfreesboro–
- Nashville, TN: 37 miles
- Atlanta, GA: 218 miles
- Charlotte, NC: 409 miles
- Cincinnati, OH: 310 miles
- Memphis, TN: 245 miles
- Richmond, VA: 667 miles
Airports:
Nashville International Airport, 33 miles from the tour start location, is served by most major airlines, with 50 nonstop markets. www.flynashville.com.
Ground Transit:
Taxi cabs are available at the Nashville airport. A complimentary Carolina Tailwinds shuttle will be available to and from the airport at a designated time before and after the tour. This complimentary shuttle typically departs the Nashville area in the 8:30 – 9:30 a.m. time frame on the morning of Day 1.
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. Your return flight should be no earlier than 7:00 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 nearby Nashville if you have time.
Country Music Hall of Fame: Learn about the history and traditions of country music and its evolution within the Music City. http://countrymusichalloffame.org/
Belle Meade Plantation: A historic plantation mansion. Tour the grounds which include the mansion, carriage house, slave quarters and a winery. http://bellemeadeplantation.com/
The Ryman Auditorium: Formerly the Grand Ole Opry. During the day take a tour and stand on the iconic stage or catch a live show in the evening. http://www.ryman.com/
The Hermitage: Tour the mansion and grounds which was formerly home to President Andrew Jackson. http://www.thehermitage.com/
Natchez Trace Parkway: The longest National Park in the U.S. A scenic 444 mile road that meanders along a former trade route. http://www.nps.gov/natr/index.htm
Hiking and Biking: A short drive from Nashville, Percy & Edwin Warner parks make up one of the largest municipal parks in Tennessee. You can hike the many trails, ride your bike on the 11 miles of one way road, or mountain bike through the beautiful forested park.
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?
Explore charming downtown Murfreesboro and learn about its rich Americana heritage, including its significance in the Civil War
Relax in the rustic yet luxurious woodland setting of Evins Mill resort, with a babbling creek just off your private balcony
Experience the world-famous distillery in Lynchburg, Tennessee, and learn about the fascinating history of America's highest-selling whiskey
Climb a famous ascent to the top of the Cumberland Plateau, and enjoy the thrilling descent the next day.
Pedal through McMinnville, renowned for its multitude of plant nurseries,
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.
