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Tennessee Bicycle Tour

A Six Day Cycling Vacation of Rural Middle Tennessee

Come ride the hills of the Volunteer State! Middle Tennessee is a beautiful area of rolling foothills and lightly traveled back roads. Known for the Home of Country Music and the Jack Daniels Distillery, there is a lot more for the road cyclist to savor along the way.

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. 

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Middle Tennessee

From Murfreesboro to Smithville

Tour Difficulty

Rolling Terrain, With a Few Challenging Climbs


6 Days, 5 Nights


Hilton Garden Inn, Murfreesboro, TN

Nearest Airport

BNA Nashville International Airport


From $2725 per person


9/22/24 - 9/27/24 9/29/24 - 10/4/24

Tour Status

Both dates are available for enrollment. Note: availability can change very quickly. Please contact us before making travel plans. info@carolinatailwinds.com
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This is an excellent tour. The route, the inns, the guides and the guests all combined to make it a memorable trip. I'd be happy to do it again (after I work my way through the rest of the hilly ride catalog!). As always, you've thought of everything and maintained the high standard that we've come to enjoy and appreciate.
Mark, Paoli, PA

ItineraryDownload Itinerary

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.

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 by Big Falls 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 Archeaological 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

50–50 miles, hilly terrain

Today, we will descend off of the Cumberland Plateau and roll 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 Evin's 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 Evin's 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 Great Falls Dam. Numerous scenic overlooks on today's route provide some of the best views along the Eastern Highland Rim. Stop along the way to see if you can spot some of the world's best freestyle kayakers playing in the rushing whitewater below. We will have a catered lunch today near Great Falls, a cascading 30-foot horseshoe waterfall. We return for another evening in the charming Evins Mill Retreat. 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. Lunch and showers are available prior to departure.


$2,725 - $2,825
Bike Rental
Single Room Supplement

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


5 nights at boutique inns


Dinner on Nights 1, 3, 4 & 5; All lunches; All breakfasts; snacks; and hors d'oeuvres most nights.

Services of Expert Local 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 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 tour date.

More details on what's included: 

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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.



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. timeframe 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 the 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.


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