Itinerary

Day 1: Natchez to Sunken Trace

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 diversion 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 reach the Mount Locust Historic House, 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 Old 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.
Meals: lunch, dinner, Lodging: Anchuca or The Duff Green Mansion
Distance: 47 miles with up to 1,940 feet of climbing

Day 2: Port Gibson to Ridgeland

This day begins with a hearty Southern style breakfast at Anchuca. 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.
Lodging: TownePlace Suites or AC Hotel
Distance:standard, 64 miles with up to 2,140 feet of climbing

Day 3: Ridgeland to French Camp

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. 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. 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.
Lodging: French Camp Bed & Breakfast
Distance: 83 miles with up to 1,485 feet of climbing

Day 4: French Camp to Tupelo

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.
Lodging: Best Western or Hotel Tupelo
Distance: 88 Miles with up 2,350 feet of climbing

Day 5: Tupelo to Florence

This day offers lots of regional music history! Since we are in Tupelo, we visit the grounds of the Elvis Presley Birthplace for a walking tour of the park before our ride.
We then 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.
Departing Pharr Mounds we soon cross the Tennessee–Tombigbee Waterway, a 234-mile waterway system from the Tennessee River to the junction of the Black Warrior-Tombigbee River.
Continuing northward along a recently paved and beautifully meandering section of the Trace. We enter Alabama by crossing over Bear Creek and begin a gentle ascent to the Freedom Hills Overlook. From here it is a fast descent to where we end the ride near Cherokee Alabama.
And now for the best part! After lunch at the end of the ride, we shuttle towards our lodging in Florence, but not before stopping for a guided tour of the Muscle Shoals Sound Studio!
This is an absolute top destination during our week-long tour. After the studio tour we end at our lodging and walk a short distance to perhaps one of our finest meals of the week in downtown Florence, Alabama.
Lodging: Hampton Inn
Distance: 55 Miles with up to 2,500 feet of climbing

Day 6: Florence to Meriwether Lewis National Monument

Shuttling from Florence, we return to the Trace to begin todays ride. 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 a very humbling place to visit.
We end the ride at the Meriwether Lewis National Monument and then shuttle to accommodations in Linden Tennessee.
Lodging: Commodore Hotel & Cafe
Distance: 68 Miles with up to 2,375 feet of climbing

Day 7: Meriwether Lewis National Monument to Nashville

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. 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 Metropolitan Nashville.
Distance: 57 Miles with up to 3,365 feet of climbing

* This is a general itinerary. Tour itineraries are subject to change based on the group, available accommodations and other unforeseen circumstances such as the weather, local conditions, government intervention, that may affect the quality of the trip and/or safety of the participants. Please view this itinerary as an outline as to what to expect on this tour.

Lodging

Natchez Trace Parkway

Night 1: Anchuca or The Duff Green Mansion, Vicksburg, MS
Night 2: TownePlace Suites or AC Hotel, Ridgeland, MS
Night 3: French Camp Bed & Breakfast, French Camp, MS
Night 4: Hotel Tupelo, Tupelo, MS
Night 5: Hampton Inn, Florence, AL
Night 6: Commodore Hotel & Cafe, Linden, TN

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.

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.

Included:

• 6 nights lodging
• All meals included, (except for Dinner on Night 2 in Ridgeland and Dinner on Night 4 in Tupelo)
• Guide service.
• Entrance fees .
• In tour shuttles and mechanical support.(during the tour)

Not included:

• Night before and after the tour not included.
• Bike rental. Be sure to bring your own helmet. We have a very limited supply and will only pack them if special arrangements are made ahead of time.
• Flights to and from the trip.
• Gratuity guides.
• Alcoholic beverages

Pricing / Tour dates

Tour price 2025: $ 3525.-pp. Single fee $ 495.- * 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).
Bike rental:
Scott Addict 10 $ 250.- per week
Scott E-bike road bikes with straight bars $ 395.- per week
Tour Dates 2025:
11 Oct – 17 Oct,
20 Oct – 26 Oct
29 Oct – 04 Nov
Tour dates 2026:
28 Mar – 03 Apr
06 Apr – 12 Apr
16 Apr – 22 Apr
25 Apr – 01 May
10 Oct – 16 Oct
19 Oct – 25 Oct
28 Oct – 03 Nov

Arrival Airport Option #1 – Nashville, TN: Guests fly into Nashville International Airport (BNA) or drive to Nashville, TN.

Arrival Airport Option #2 – Jackson, MS: Guests fly into Jackson–Medgar Wiley Evers International Airport (JAN).

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

Day 0: 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 our 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 our 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.

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.

Conditions

Deposit $950.00 p.p.
The deposit payment for a tour must be paid within two weeks after the booking is confirmed.
The remaining payment is due 90 days before the start of the tour.
For tours that are booked within 90 days before the start of the tour you will pay 100% of the tour price

Information

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. 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, 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.

Meals:
We 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. 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”.

Lunches: Our 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. We 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