Natchez Trace Parkway - Lizard Head Cycling Guides
107 Aurum St, Box 855, Ophir, CO 81426 970.728.5891

Natchez Trace Parkway

Please click here to jump to the Overview section with all tour details including pricing.

Natchez Trace Parkway: Highlights

NOTE: This is one of our most popular tours and tour dates fill up fast, so make your reservations NOW to secure your spot!

The Natchez Trace Parkway is one of North America’s best hidden gems. With vast stretches of twisty roads with little vehicle traffic, tremendous scenery over ridges and through isolated hollows, undulating terrain with no big climbing, and with many small friendly towns steeped in history, it is no wonder that the Natchez Trace (also known simply as the “Trace”) is a destination for many cyclists looking to reconnect with nature while pursuing their love of cycling.

The Natchez Trace, also known as the “Old Natchez Trace”, was a historical foot path that extended roughly 440 miles from Natchez, Mississippi, to Nashville, Tennessee. The Old Natchez Trace was first created by migrating animals and then used for centuries by the regional tribes of the Cherokee, Choctaw, Chickasaw, and Natchez for trade and travel. After the Americas were formed, the Trace was then used by early European and American explorers, traders, and emigrants in the late 18th and early 19th centuries as a route to the “wild frontier”. In the 1800’s boatmen known as the Kaintucks would float barges of goods down the Ohio and Mississippi rivers to Vicksburg, Natchez, Baton Rouge, and other points south. After they sold their goods, the Kaintucks would travel by foot on the Trace to return back north to Nashville, Tennessee. Today, the trail is commemorated by the 440 mile Natchez Trace Parkway, which is a modern highway that follows the approximate path of the Old Natchez Trace.

The riding experience on the Trace is similar to a 440+ mile “bike path” with no stop signs, no large cities, very low traffic, a wonderfully smooth surface, beautiful scenery, and tons of history… you just ride without a worry!

Why Ride the Natchez Trace from South to North?

That is a great question and we are glad that you asked! Unlike many other outfits offering multi-day cycling tours along the Natchez Trace Parkway, we did our research and discovered that a South to North tour is just a better overall experience. Here are a few reasons why:

  1. Mile Markers: On the 440+ mile Natchez Trace Parkway, Mile Marker 0 starts in Natchez, Mississippi. Plus it is more fun to add up miles rather than count down!
  2. The Sun: When riding from South to North, the sun is primarily behind the riders for the duration of the tour allowing one to enjoy the scenery along the way and not blinding a rider’s view as it does from North to South.
  3. Wind: The prevailing winds in this region come from the Southwest to West and traveling the Natchez Trace from South to North is primarily in a Northeasterly direction, thus the likelihood of a tailwind is greater… although not guaranteed, of course!
  4. History: The previously mentioned Kaintucks would travel by foot or horseback back North along the Natchez Trace to Nashville. As one rides North they retrace the historical route that the Kaintucks (who were now loaded with cash!) took as they faced a daunting and sometimes dangerous trek as they battled the environment, the natives, and sometimes, an ambush from robbers!
  5. Seasons: Riding from South to North along the Natchez Trace in early autumn is a metaphorical transition from a summer into autumn season as one enjoys cooler temps and autumn like foliage entering into Tennessee at the end of the week. Also, when riding from South to North in the spring riders enjoy increasing spring like conditions and wildflowers as they travel from the warmer climate of the South.
  6. Fitness: Riding from North to South is just as “hilly” as it is riding from South to North. However, with the flatter terrain in Mississippi and the hillier terrain in Tennessee, going from South to North allows a rider to “acclimate” along those flatter miles during the first 5 days of the tour making the hills of Tennessee will seem easier to ride at the end of the week after gaining better fitness.
  7. Logistics: Riding from South to North makes the end of tour logistics easier for riders since they end back at their car in Nashville or take a plane back home. The closest airport to Natchez is in Jackson, Mississippi, 2.5 hours to the northeast, or shuttling back to Nashville from Natchez by car which is an entire days drive. Taking care of these travel logistics pre-tour makes for a much more enjoyable post-tour experience.
Natchez Trace Parkway

Natchez Trace Parkway

The Natchez Trace is a beautiful road

Double Arch Bridge

Double Arch Bridge

Below the Double Arch Bridge

Natchez Trace Parkway: Testimonials

Read what previous guests on our Natchez Trace Parkway bike tour have been saying…

This was all in all a great ride. It is my second with Lizard Head and won’t be my last. I enjoyed the choice of hotels and restaurants, not just the run of the mill accommodations. The support team, Peter and MJ, did a great job – always good food, including variety, at stops. The communication prior to the ride was complete and there were no surprises. Thanks for putting together a great tour and I will look forward to my next. – Craig

My friends and I just got back home from our Natchez Trace trip, and wanted to let you know we had a fabulous experience, largely due to our guides, Heidi and Peter. Peter is so knowledgeable about the area and its history, and has a deft touch with food. But, for me, the trip was made by Heidi, who has a real gift for interacting with customers, and made each of us feel so welcomed and cared for. Trust me, thanks to Peter and, particularly, Heidi, this will not be my last Lizard Head tour. Thanks! – Kevin

I want to tell you how much I enjoyed the (Natchez Trace Tour)! Our guides Wylie and Matt were super guides. Both are multi talented, doing whatever they could to make our trip enjoyable. The trip was very enjoyable, and I look forward to another tour with Lizard Head in the near future. I will definitely recommend your company to my fellow cyclists whenever I have an opportunity. – Allen B.

Absolutely no complaints about the trip. Both Peter and Roy were fantastic. We had a few special requests and everything was done with enthusiasm and a smile. These two are professionals and you are lucky to have them. – Anthony

Just a short note to tell you how much I enjoyed the Natchez Trace tour. First and foremost, the tour leaders Peter and Rick were fantastic. You could not ask for better people to lead this tour.

I thought the accommodations were great. I really liked the mix of Southern Charm, local and historic and more modern hotels.

The food on the trail was fantastic. The breakfasts were great and hearty. The dinners were good and liked that you did not place limits on what could be ordered.

I really enjoyed the mix of people with whom we rode. From some folks that had never ridden a road bike before, to a guy who was one of the best cyclist I have ever ridden with, everyone had fun.

I hope to save up my pennies and do another tour with your company soon. But until then, I will sing your praises. – Perry

The Natchez Trace tour was my first tour. I will say Peter and Rick set a very high bar… it was a wonderful experience. The route, the support and the group were all awesome. I can’t say enough about Peter and Rick – they worked super hard, went above and beyond with things like cooking meals on two evenings and making the overall experience truly memorable. I will definitely be back on another tour in 2022!! – Jeremy

Thanks again for another fantastic tour! We enjoyed our perfect tour very much and certainly plan to come back to Lizard Head for more tours. – Joanna

Peter and Rick were great, one of the best bike tours I have done (this was #37). They were relaxed and in control the whole way, and pulled off some amazing “home” cooked meals along the way. A great zen like ride, loved it! – Scott

I have just completed the Natchez Trace Tour with Peter and Rick as my guides. They did an outstanding job managing my food allergies! Thank you and your company for helping it to be a fantastic week tour. – Jane

Never having been on a Lizard Head trip before, this trip was a great new experience for me. The real adventure is seeing a new part of the country, and meeting new friends that share a passion to be active, outside, and sharing ideas. I think I came up with a new life principal on this trip, “It’s never too late to have a happy childhood!” – Paul

I had an absolutely wonderful week on the Natchez Trace. We were fortunate to have participants who had common values in addition to cycling. We could roll, eat and sleep trouble free. I look forward to my next trip with LHCG. – Paula

I was highly impressed with Peter and Rick on the recent Natchez Trace ride. Punctual, efficient, knowledgable, always offering above and beyond service. They set the tone for your company. The accommodations were varied and terrific. The miles per day were perfect, not the ho-hum 20-40 mils per day. I ride a Scott CR Pro so was pleased that you use Scott bikes. I recommend the trip to my friends. – Stephen

Click here for a wonderful narrative of the our Natchez Trace Parkway bike tour by Stephen.

I was able to have a(n) enjoyable trip. The credit definitely goes to Peter and Roy … (t)hey are consummate professionals and a credit to your company. I would definitely love to take another trip with either or both of them. – Deb

The Natchez Trace Parkway Tour was my first tour with the Lizard Head Cycling Guides, but it won’t be my last. I have cycled with another company Coast to Coast and they couldn’t light a candle compared to your company! Roy and Peter, our guides, were consummate professionals. They handled our luggage, made delicious lunches, maintained our bikes, took turns cycling with us, provided side excursions to Elvis’s home in Tupelo, Sonics, Waterfalls, etc., as well as van transportation to our lodging. Wow! They truly made the cycling experience a special one.

The lodging was a mix of unique B&B’s, hotels, cabins, and even a mansion! Sweet! The restaurants were great as well. I enjoyed ordering anything from the menu including dessert. The route and directions were easy, albeit back to back 85+ mile days were a challenge. But I was there to cycle and meet the challenge of cycling the Natchez Trace Parkway.

Thank you again for a memorable cycling tour! – Jenny

This trip exceeded my expectations in many ways:

1. Manicured wilderness for 450 miles — like being on a Yellow Brick Road through an Appalachian Spring. Quite exhilarating and mostly NO TRAFFIC! I swear there was only one car on day one (OK, there was a threat of tornado, but more on that later)

2. The spring foliage and flowers were mesmerizing. Fields of red clover (never seen before), delightful azaleas, brilliant dogwoods, and lots of other flowers.

3. The route leant itself extremely well to perfectly spaced and safe break locations.

4. I really loved the small towns for their charm, authenticity and one-of-a-kind uniqueness. And of course supremely friendly hospitable people. Completely unpretentious. The manor in Vicksburg blew me away. The caretaker casually and graciously made us old fashioneds with well-muddled cherries as tornadoes were passing overhead (touched down only 4 miles away!). Talk about keeping cool in the eye of the storm. That evening added some exciting adventurous spice to the tour.

5. Guides also kept their cool while they kept their eye on the radar, etc. The guides were a good blend of personalities (one more free-spirited, the other more grounded).


(The Natchez Trace) has been on my bucket list for years, but I’ve been unable to do it. I can’t begin to tell you how WONDERFUL it was, how GREAT the food and lodging were, and how AMAZING Peter and Roy are! I am not a fast rider, and they still made me feel as if I was … ‘Lance’ … lol. – Lori

Kent and I had a fun time on the ride from Natchez to Nashville. Peter, Peter and Anna did a great job handling all the logistics which many times were quite tricky. – Linda

I just wanted you know that Candice and I really appreciated your energy, consideration, and organization this past week of cycling. Although some days were tough we felt a sense of accomplishment at the end of the tour. – Cathy

I am back from the Trace and just wanted to let you know that I had a really good time. History element was a big part of it. I especially want to let you know how good a job Matt and Peter did. They were professional, calm and super guides. – Lucy

I just completed the Natchez Trace Bicycle Tour. It was a great tour. The route was outstanding. Limited auto traffic and very courteous drivers that went out of their way to be polite. Peter and Anna are the best tour guides I have ever ridden with. They made road details clear and easy to understand. They were very supportive for all the riders regardless of a rider’s pace. They kept us all properly supplied with water and nutrients during the ride. Their professionalism is definitely 5 star! Thank you for the tour. I am glad I choose this tour from the Lizard Head list. – Jeff D.

Natchez Trace Parkway: Dates

Potential tour dates are listed below and not all tour dates will run. Lock in your preferred tour date early as unopened tour dates will be closed. Please see the Spring/Autumn Tour Calendar and the Summer Tour Calendar for confirmed departures. Any unopened date can be a Custom Week (9 riders required). Please contact us via email or call 970.728.5891

To easily register for a particular tour, please click the Book Now! link after the tour date listed below. This will select the tour name and the appropriate date on the registration form.

2023 Tour Dates

  • October 9 to 15, 2023 Monday to Sunday (Book Now!) – TOUR A GO!
  • October 20 to 26, 2023 Friday to Thursday (Book Now!) – TOUR OPENED 4 riders needed to make GO
  • October 28 to November 3, 2023 Saturday to Friday (Book Now!)

2024 Tour Dates

  • March 31 to April 6, 2024 Sunday to Saturday (Book Now!)

  • April 8 to 14, 2024 Monday to Sunday (Book Now!)
  • April 19 to 25, 2024 Friday to Thursday (Book Now!)
  • April 27 to May 3, 2024 Saturday to Friday (Book Now!)

Tour Status Notes: NO STATUS = Date Set, no riders have signed up. TOUR OPENED = Tour Opened, rider minimums not met. TOUR A GO! = Tour is Go, rider minimums met. SOLD OUT = Tour Full, rider maximums met.

Natchez Trace Parkway: Overview

Reptile Rewards

Tour Length: 7-Days Cycling/6-Nights Lodging

Arrival Airport Option #1 – Nashville, TN: Guests fly into Nashville International Airport (BNA) or drive to Nashville, TN.
See more information in the Itinerary below under Day 0.

Arrival Airport Option #2 – Jackson, MS: Guests fly into Jackson–Medgar Wiley Evers International Airport (JAN).
See more information in the Itinerary below under Day 0.

Meeting Town & Hotel: Natchez, MS at the designated meeting hotel provided in the tour confirmation documents. Guests on-their-own for reservations at the designated meeting hotel or at other nearby hotels or inns this evening.

Ending Town: Nashville, TN at the designated ending hotel provided in the tour confirmation documents.

Departure Airport: Nashville, TN – Nashville International Airport (BNA).

Post-Tour Logistics: The Natchez Trace tour ends on Day 7 between 4-5:00 PM at the designated ending hotel near the Nashville Airport. Although we do not recommend a same day flight when the tour ends on Day 7, please make your flight reservation for 7:30 PM or later to avoid undue stress as things can happen during the last day that may delay our arrival back in the Nashville area.

Total Miles: 300 to 440 miles, additional mileage options available. (Can I keep up on this tour?)

Ability Level: Intermediate (2/3)  to Upper Intermediate (3) 
There are moderate climbs on the last two days of the Natchez Trace tour, but overall there are very few big climbs along most of the Trace which makes even the longer mileage days relatively easy. This is a very leisurely tour along a magnificent ribbon of extremely well maintained pavement.

Tour Cost: $3,355 per person with shared accommodations. Add $495* per person to the Tour Cost for a private room each night of the tour (includes 6-Nights). Group discount of $200 per person for groups of 4 or more.
Please see our Tour Discounts Policy.

*Please note that due to the historic nature of some of the accommodations, those choosing the private room supplement may have a shared bathroom with one other person on some nights. Otherwise, the rooms are private. As a result, the private room supplement cost for this tour is $495 for the 6-nights versus the standard $100 per night (or $600).

Tour Includes: 7-Days guide service, 6-Nights lodging, all meals (except for Dinner on Night 2 in Ridgeland and Dinner on Night 4 in Tupelo), entry fees, energy food, liquid refreshments, in-tour shuttles, and mechanical support. Alcoholic beverages and bike rental are additional.

Non-Riding Spouses & Partners on Tour: If a non-riding spouse or partner would like to join you on tour and they have their own transportation, they can stay in your room for the cost of the tour's single room supplement. Non-Riding spouses and partners can join a tour's meal plan of three meals a day for $85 per day.

Lodging Includes 6-Nights: (subject to change based on availability) The Natchez Trace is a historic trail and some of the lodging is historic in nature. This is part of the charm of traveling on the remote Trace.

Meeting Hotel and Ending Hotel reservations and costs are NOT included unless specified otherwise. Guests are on-their-own to make reservations at the Meeting Hotel or Ending Hotel, or other nearby hotels.

Road Bike Rentals

NOTE: The make, model, and specifications of rental bikes may differ from what is described below. Please contact us if you have any specific needs for a rental bike or have any questions about rental bikes.

Lizard Head Cycling Guides is proud to rent Scott Bikes. The Scott Addict 10 Disc was designed from the ground up with those longer days in mind. With geometry that is less focused on racing and more on enduring, the Addict 10 will be your go to when you’re looking to put the miles in.

The Scott Addict 10 Disc features: Carbon Frame and Fork, Shimano Ultegra 2x11 Drivetrain, 34x32 Compact Gearing, 30mm Tires, and Hydraulic Disc Brakes. Approx. Weight: 16.89 lbs / 7.66 kg (without pedals)

Learn More: Click Here to learn more about our Road Bike Rentals including pricing.

Road E-Bike Rentals: Click Here for more information on our Road E-Bike Rentals including pricing. Please note that E-Bikes are not available for certain tours including those that involve camping. Please contact us for more information before registering for a tour. NOTE: E-Bikes are great, but our tours are designed to be ridden without motorized assistance. We offer "bumps" along the road so that everyone can stay together.

Tandems and Recumbents: Lizard Head Cycling Guides happily accommodates both tandem and recumbent bikes on our tours.

If you have any further questions, please read more on our Rental Bikes FAQ page. You can also email us at or call us at 970.728.5891

Meals On Tour

Lizard Head Cycling Guides provides most meals on all tours (unless otherwise noted) including breakfast, lunch, and dinner. Guides will prepare a daily lunch en route for nearly every tour, both road and off-road, as well as provide nutritious snacks at periodic aid stations during the day.

Most of our road tours utilize local restaurants for all meals and occasionally guides may prepare a dinner or two during a tour. Due to the nature of being "off the grid", most of our off-road tours feature guide prepared meals for breakfast, lunch, and dinner. FUN NOTE: When guides prepare a meal in camp and the guests sit around and watch, this is called "Guide TV". :)

We also pride ourselves on being able to cater to specific dietary requests and needs, so rest assured that you will be able to get the nutrition that works best for you during your tour. Gluten Free, Dairy Free, Vegan, or a someone who loves it all – we will keep you well fed during the tour!

Lunches: Lizard Head Cycling Guides prepares healthy lunches to keep you going. We will serve you fresh organic fruits and veggies, salads, hummus, sandwich fixings, nuts, gourmet cheeses and, of course, plenty of salty/sweet snacks such as chips and cookies.

Dinners: On our road tours, Lizard Head Cycling sources our favorite restaurants in each town that we visit. Our guides focus on establishments that offer fresh and local ingredients and guests choose whatever they desire to eat off the menu including: appetizer, salad, entrée, and of course, dessert... yum! :) Also, while on tour if a guest wants to dine early before the group and go to bed, this is fine. We understand that on some days sleep is the most important post-ride element.

Ability Level: Can I Ride This Tour?

Definition of Ability Levels

= Intermediate (2/3) Rides and/or takes spin classes 1 to 3 times a week for a total of 50 or more miles.
= Upper Intermediate (3) Rides and/or takes spin classes 2 to 4 times a week for a total of 75 or more miles.
= Advanced (3/4) Rides and/or takes spin classes 3 to 5 times a week for a total of 100 or more miles. Has ridden multi-day tours and done a century ride.
= Expert (4) Rides 4 or more times per week totaling 150 or more miles. Rides E.F.I. with regularity. Has done numerous multi-day tours, century rides and races.

How Fit do I Have to Be? If one month prior to the tour, you can ride 2 to 3 times a week equaling a total of 75 or more miles a week, you'll do just fine. We like to jokingly say that "one is ready for a Lizard Head Cycling Tour when they are finished with tour" and this is true! The only way to simulate a week long bike tour is to go on a week long tour.

Our average rider age is 55 years. These are bike tours, not races so we take our time to stop, take pictures and see the sights. We have all day to reach our destination and most riders take "bumps" at some points. We offer reduced mileage options for each day. Of course if someone wants to ride E.F.I. (Every Freaking Inch), we love to show them all the extra climbs, loops and hidden canyons that can be included!

Do the Bump! Daily mileage options allow cyclists of varying abilities to enjoy this tour. One of our favorite options is to give cyclists a "bump" via the support vehicle, or a 10 to 20 mile lift down the road representing an hour of pedal time. After the bump the rider is "off the front" and riding at his or her own pace without feeling they are being left behind the group. They'll then have time to linger and take in the spectacular scenery. All cyclists come together in time for lunch. Afterwards, cyclists can take another bump and/or continue riding.

Seamless Mileage Options: Lizard Head Cycling Guides designs multiple mileage options for each tour – something we're well known for in our business. This technique is similar to heliskiing in that one does not ski everything, they ski the best. 🙂

Slow or Fast? Many cyclists who sign up for our tours have worried themselves silly about not being able to keep up, but then they're surprised to find that all the worrying was about nothing. They do just fine! Slow and Fast only exist relative to other cyclists. Speed does not matter as long as one is moving on the bike. As long as one is moving, they are truly going fast enough.

If you have questions about your ability to ride this tour, please contact our office via email or call us at 970.728.5891 - we'll more than happy to guide you!

Please also see this blog post for more information.

Overall Route Map

Below is an example of the daily routes for this tour and are subject to change based on season, available accommodations, road closures, and other factors. The actual routes will be made available to registered participants before their tour, so please view these routes as a general outline as to what to expect.

Natchez Trace Parkway: Itinerary*

*Tour itineraries are subject to change and modification based on the group, available accommodations, road construction, road closures, and other unforeseen circumstances including weather, wildfires, flooding, hurricanes, landslides and/or other acts of nature. Also, the distances and elevation profiles shown below may not reflect the actual distances and elevations while on tour as these are provided here to give an idea as to the anticipated mileage and terrain. Please view this itinerary, the distances, and elevation profiles as a general outline as to what to expect while on this tour.

Day 0: Pre-Tour Travel to Natchez

Day 0 is the day before the tour starts. The below information is for planning purposes only. Complete and detailed logistics information will be included in your tour confirmation documents.

PRE-TOUR SHUTTLE FROM NASHVILLE, TN ON DAY 0 – A 6:30 AM pre-tour shuttle from Nashville, TN to Natchez, MS on Day 0 is available with Lizard Head Cycling Guides when reserved in advance. The cost is $105/pp which includes transport of you, your gear, and your bicycle. Please let us know in advance if you are bringing a tandem, a recumbent, a bicycle case, or any other cycling machine so that we can accommodate for them. Although we break en route for food, meals during the shuttle are not included. If you are driving to Nashville, we recommend that you leave your vehicle for long-term parking at the designated meeting/ending hotel.

  • NOTE: The designated meeting/ending hotel in Nashville, TN has a daily fee when leaving a vehicle long-term in their parking lot after checking out, so please check with the front desk beforehand. You must have stayed at the designated meeting/ending hotel to park long-term there, otherwise you will need to find other long-term parking options such as the nearby The Parking Spot Nashville Airport or Executive Travel & Parking.

PRE-TOUR SHUTTLE FROM JACKSON, MS ON DAY 0 – Guests fly into Jackson, MS (Jackson–Evers International Airport – JAN) on or before Day 0. A pre-tour shuttle from Jackson, MS to Natchez, MS on Day 0 is available with Lizard Head Cycling Guides when reserved in advance. The cost is $45/pp which includes transport of you, your gear, and your bicycle. Please let us know in advance if you are bringing a tandem, a recumbent, a bicycle case, or any other cycling machine so that we can accommodate for them. The shuttle arrives at the Jackson–Evers International Airport between 3:00-3:30 PM, departs no later than 3:30 PM, and arrives around 5:30 PM in Natchez, MS.

  • NOTE: Flight delays and cancellations are common when flying into Jackson–Evers International Airport. If possible, we highly recommend flying in a day early to help avoid this, but if you must fly in on Day 0, please make your flight arrival into Jackson, MS no later than 12:00 PM local time to help offset any possible delay.
  • Guests can also make their own shuttle arrangements from Jackson, MS to Natchez, MS with Downtown Karla Brown. Guests will need to work with the shuttle time set by the first guest to make this reservation.
  • Enterprise Rent-A-Car also offers one-way car rentals from Jackson, MS to Natchez, MS. However, please check with the Enterprise Rent-A-Car office in Natchez to assure drop-off as their operational hours vary or may not be open, especially on weekends.
  • Guests are on-their-own for reservations at the designated meeting hotel in Natchez, or at other nearby hotels or inns this evening.

Meeting Hotel and Ending Hotel reservations and costs are NOT included unless specified otherwise. Guests are on-their-own to make reservations at the Meeting Hotel or Ending Hotel, or other nearby hotels.

Day 1: Natchez to Sunken Trace
47 Miles with up to 2,275 feet of climbing

Our first day of the tour begins with a meet and greet of guests and guides followed by a short presentation of the week ahead plus a brief history of the Natchez Trace. We will fit bikes, load gear into the support vehicle, and then saddle up to ride to the start of the Natchez Trace Parkway’s southern terminus to begin our week-long journey north.

Today’s route is low mileage so that riders can stretch their legs and get warmed up for the longer days ahead. At mile marker 10, riders make a short divert from the Trace to view the Emerald Mound Site – an ancient ceremonial mound built by the ancestral Natchez that dates from the period between 1200 and 1730 A.D.

After Emerald Mound and back on route, riders will soon make another quick divert to Mount Locust Historic Home, the last remaining stand (aka: inn) along the Trace and one of the oldest surviving structures in Mississippi. While riders take a tour of this house, guides will prepare a gourmet lunch in the parking area. After lunch, we finish the day by meandering our way along the Trace just past the small town of Port Gibson, MS (the town General Ulysses S. Grant proclaimed was “too beautiful to burn”) and end the ride at Sunken Trace – a beautifully preserved portion of the centuries old deeply eroded Natchez Trace foot path.

From Sunken Trace we shuttle a short distance to Vicksburg, MS to check into the Anchuca Historic Mansion and Inn. Guests will have time before dinner to stroll this small town or to relax at the inn after the adventures of the day.


Day 2: Sunken Trace to Ridgeland
64 Miles with up to 2,535 feet of climbing

This day begins with a hearty Southern style breakfast at Anchuca and then a shuttle back to the Natchez Trace Parkway to start from the Sunken Trace where we ended the previous day. During the morning’s ride we make a stop at the Rocky Springs Site for a quick tour of the old Rocky Springs town site.

After Rocky Springs the route continues to thread it’s way through the dense ancient hardwood forests, past open pastures and fields with lunch held at Dean Stand. After lunch there is a stop at the Clinton Visitor Center for an aid station. The Center is constructed with period materials and period architectural details including a porch and “dogtrot” and has the look and authentic charm of one of the 19th century farmhouses once located along the Natchez Trace.

After departing the Center, we finish the last miles of our journey along the Natchez Multi-Use Path and leave the Trace to check into our lodging for the night in Ridgeland, MS.


Day 3: Ridgeland to French Camp
82 Miles with up to 1,745 feet of climbing

On this third day of the tour, the mileage increases yet again, but since this is one of the flatter portions of the Trace, the miles you pedal today will pass by quickly. Departing the hotel, we make our way back onto the Natchez Multi-Use Path for the first five miles making our way to the reservoir overlook. After departing the overlook, riders are back on parkway and one of the highlights of this morning’s portion is the ride along the Barnett Reservoir for about 8 miles where wildlife such as egrets, herons, and even eagles can often be seen along the way.

At mile marker 122, make a stop at the Cypress Swamp where a boardwalk trail leads over the murky waters through a tupelo and bald cypress swamp… make sure to watch for alligators! The lunch stop is at the Kosciusko Information Center in Kosciusko, Mississippi – the town is named after General Tadeusz Kosciuszko, a Polish military genius and engineer who played a pivotal role in the American Revolutionary War.

By the end of the day, we arrive at the French Camp Historic District, a period reconstructed log-cabin village where riders can relax and enjoy a guide cooked dinner in this most remote area of all of Mississippi.


Day 4: French Camp to Tupelo
88 Miles with up 2,800 feet of climbing

Today presents the longest day along the Trace. However, we will start early and riders will have plenty of time to casually pedal along enjoying the scenery of the Red Clay Hills before settling into the bottom lands near the headwaters of the Big Black River. The miles will seem to zip by along this quiet section of the Trace, with only a few minor hills and minor changes in the uniform surroundings. Just past Houston, Mississippi are the Bynum Mounds – six burial mounds and an associated habitation area built between 100 B.C. and 100 A.D.

The ride ends at the Parkway Visitor Center and our destination for the evening is Tupelo, Mississippi – birthplace of Elvis Presley – where our lodging, dinner, and post-ride relaxation await.


Day 5: Tupelo to Colbert Ferry
62 Miles with up to 3,300 feet of climbing

After breakfast at the hotel, we pack up and shuttle a short distance back to the Trace to depart from the Parkway Visitor Center to continue our northward journey. Partway through our ride we make a stop at the Pharr Mounds – a complex of eight dome shaped Tumulus burial mounds built between 100 and 200 A.D.

We then continue our ride soon crossing the Tennessee–Tombigbee Waterway (aka: the Tenn-Tom) and then stop to have lunch at Bear Cave Spring where a collapsed underground limestone cavern formed and Paleo hunters who used the nearby Bear Creek Mound site likely used this cave as a water source. The ride ends at Colbert Ferry and from here we shuttle to our lodging in Florence, Alabama.


Day 6: Colbert Ferry to Meriwether Lewis National Monument
60 Miles with up to 2,800 feet of climbing

Shuttling from Florence, we return to Colbert Ferry to begin todays ride and the scenery remains world-class – from the wooded ridges to the steep hollows carved by brooks cascading over rocky stream beds. On this day we also reach the highest point along the entire Trace to 1,100′ above sea level.

Soon after getting onto the Trace we will take a short diversion to view the Wichahpi Commemorative Stone Wall (a.k.a: Te-lah-nay’s Wall) – a stone wall hand built by Tom Hendrix to commemorate his great-great-grandmother’s, Te-lah-nay, journey of being forced from her native lands in northwest Alabama and then returning during the Trail of Tears period of early American history. This is a must see and very humbling place to visit.

We end the ride at the Meriwether Lewis National Monument and then shuttle to this evenings accommodations in Linden, Tennessee.


Day 7: Meriwether Lewis National Monument to Double Arch Bridge
57 Miles with up to 4,065 feet of climbing

The final day of the tour has arrived and we have saved what we think is the best of the Trace for last! Following breakfast we will shuttle from Linden back to the Meriwether Lewis National Monument. Here while riders check out the monument to a great American explorer, guides will get the bikes ready for the final leg of the Trace.

Riders roll away and soon enjoy the magnificent scenery along the twisty turns and rolling hills on this final section of the Trace. At mile marker 438 you will ride across the gracefully designed Double Arch Bridge and then soon after the bridge, enjoy one last twisty descent to end at the Northern Terminus and finish the riding for the week. The tour concludes with a shuttle back to Nashville, TN.

What a week… well done!


Natchez Trace Parkway: Logistics & FAQs

Bike Shipping

Lizard Head Cycling recommends shipping with Bikes can be shipped either to our partner bike shop in each meeting town for professional assembly or directly to the meeting hotel for self-assembly. Bike boxes can generally be left at the meeting hotel during the tour. Bikes shipped across the continental US should be shipped 8 days prior to your tour.

Ride Difficulty: This custom tour is designed for ADVANCED to INTERMEDIATE cyclists with various levels of fitness. Each day there are additional mileage options for advanced riders.

Tour Support: A 15-passenger van and trailer that carries luggage, food and equipment will support this tour.

General Tour & Cancellation Policies

Please take a moment to familiarize yourself with all of our tour and cancellation policies, which can be found by clicking here.

Travel Insurance

If you have not already, now would be a great time to consider adding travel insurance to your tour. You are welcome to use any travel insurance company you would like. We recommend Generali/Trip Mate.

Generally, if contracting COVID causes clients to cancel or interrupt their tour, trip insurance companies would treat it as any other illness as long as it is contracted after the insurance was purchased. Please check your individual plan documentation for details. Please note that quarantine is usually only covered if clients are actually sick with COVID. If a state requires quarantine upon arrival because of standardized state law, coverage is generally not covered. Again, check your individual plan documentation for details.

American Guests - use this link:

  • The Premium Plan is the only plan which offers Pre-Existing coverage so long as the plan is purchased prior to Final Payment.
  • The Premium Plan is the only plan that offers an optional Cancel For Any Reason - the policy must be purchased within 24 hours of initial trip deposit, the full trip cost must be insured, and if they cancel for Any Reason, it must be 48 hours prior to departure, and the reimbursement for an Any Reason claim is 60% of pre-paid, insured, non-refundable trip cost.
  • Customer Service can be reached at 1-800-874-2442 for coverage questions and policy modifications or to purchase by phone. Agency Code: LIZA0855

Canadian Guests - use this link:

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