Mississippi: The Natchez Trace

6 days
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4.9/5 Excellent
100+ reviews  
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Group Tour
Go deep into the antebellum South on this stunning tour of Mississippi’s Natchez Trace—an ancient trail with deep roots in Native American culture. During this eye-opening tour, your VBT trip leaders will help you experience all sides of Mississippi’s past and present—including a stop at the Civil Rights Museum, a tour of grand southern plantations, a visit t...
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Trip type
Group Tour
Lodging level
Premium - 4 star
Physical level
Trip pace
Full schedule


    • Roll through centuries of history along the Natchez Trace Parkway, a National Scenic Byway and All-American Road.
    • Ponder the legacy of the Civil War at the ruins of the Windsor Plantation.
    • Relive the Siege of Vicksburg on a guided tour with a local historian as you tour Vicksburg National Military Park by bicycle.
    • Visit the sprawling Emerald Mound, one of the largest Native American ceremonial sites.
    • Customize your own “Pilgrimage” of Natchez’s stately antebellum homes.

What's this trip about?

    Go deep into the antebellum South on this stunning tour of Mississippi’s Natchez Trace—an ancient trail with deep roots in Native American culture. During this eye-opening tour, your VBT trip leaders will help you experience all sides of Mississippi’s past and present—including a stop at the Civil Rights Museum, a tour of grand southern plantations, a visit to an ancient Native American burial ground, and a tour of the historic Civil War battlefield at Vicksburg. Along the way, you’ll also discover vibrant local cultural traditions during a southern gospel choir performance and lunch at an historic home in Port Gibson. During your two nights in historic Vicksburg, you’ll find yourself steeped in southern traditions—perhaps even relaxing on the very balcony from which Jefferson Davis made one of his final public speeches.


Itinerary focusActive
Group sizeSmall Group - max of 20 people
Age range13 to 80 years
Flights and transportN/A
Start CityJackson
End CityNatchez

Travel Themes

  • Cultural
  • Cycling & Biking
  • Nature & Wildlife


  • North America


  • Jackson
  • Mississippi
  • Natchez
  • Vicksburg


  • Culture
  • Cycling
  • Historic sightseeing
  • History
  • Mountain Biking
  • Nature
  • Guided Group

Trip includes

    • Custom VBT Bike and Helmet
    • Two Local, Bilingual Trip Leaders
    • Support Vehicle
    • Luggage Transportation
    • Ride with GPS and Daily Route Notes
    • Welcome Reception
    • Facilitated Cultural Experiences
    • Your Choice of VBT Branded Gear for Your Adventure


Travel Map
DAY 1: Arrive in Jackson / VBT Bicycling Vacation begins / Warm-up ride / Welcome reception and dinner

Your Natchez Trace Trail tour begins at the Fairview Inn in Jackson, proud recipient of AAA’s elite Four Diamond rating for more than 30 years. During your overnight at the inn, you will enjoy your first taste of legendary Southern hospitality.

If you’re flying...

DAY 2: Rocky Springs / Natchez Trace Parkway / Vicksburg

After a hearty Southern breakfast, you’ll shuttle to your starting point for your first memorable ride along the scenic Natchez Trace Parkway. This pastoral parkway loosely follows the Old Natchez Trace Trail, a nearly 500-mile footpath blazed by Native Americans seve...

DAY 3: Vicksburg National Military Park

Riding out from your inn today, you’ll cycle through Vicksburg and past scenic overlooks of the Mississippi River. Your destination is Vicksburg National Military Park, home to the country’s largest Civil War cemetery. You’ll stop at the Visitor Center to watch a shor...

DAY 4: Natchez Trace Parkway / Emerald Mound

After breakfast, you’ll return via shuttle to Port Gibson, where you’ll begin another relaxing, scenic ride along the Natchez Trace Trail.

You’ll have the opportunity to set your own pace today, stopping to take in the parkway’s striking vistas as you cycle sou...

DAY 5: Antebellum Pilgrimage / Natchez

Natchez is known for its Spring Pilgrimage, an annual tour of the town’s most impressive antebellum homes. Katherine Grafton Miller, president of the Natchez Garden Club, came up with the idea in 1932, when an unexpected cold snap jeopardized the club’s annual fundrai...

DAY 6: VBT Bicycling Vacation ends / Departure

Your Natchez Trace Trail tour concludes after an included breakfast at your hotel. VBT’s complimentary shuttle will take you to either Jackson-Evers International Airport or the Fairview Inn in Jackson. The shuttle departs Natchez at 9:00 a.m., arriving at the airport...

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Dates & Availability

Price From $2,495
Price per day$416
Last Updated: 2/23/2024
Start Date
End Date
Shared Room
Single Supplement
24 Mar 2024
29 Mar 2024
07 Apr 2024
12 Apr 2024
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13 Oct 2024
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03 Nov 2024
08 Nov 2024

Check Current Availability, prices, specials with VBT Bicycling Vacations.

The total tour cost includes the tour price (regular or promotional) and the compulsory local payment. The promotional price is subject to change. Check directly with the operator for the latest price offer. The tour operator requires you to pay only the tour price to purchase your travel. The compulsory local payment will be paid when you join the trip. All prices are based on double, twin or triple share occupancy. Solo passengers will be accommodated in a double, twin or triple room according to availability with a passenger(s) of the same gender. Single supplement only needs to be paid if the passenger does not want to share and requests their own room. Discounts can only be applied at the time of booking and cannot be added at a later date, regardless of any changes made to the original booking.

Prices may vary due to local taxes and trip seasonality. Click "Request Info" to inquire directly with the tour operator for the final trip price.

VBT Bicycling Vacations Reviews & Ratings

4.9/5  Excellent
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Nov 2023

Written on

Absolutely stunning scenery with relatively easy cycling.

This tour was one of our favorites. The tour leaders (Claudio and Tiziana) were great. The Dolomites and Italian Alps were breathtaking and the bike paths and towns ...



Nov 2023

Written on

Fantastic intro to a bike vacation!

VBT came highly recommended by several friends and family so we took the plunge and did our first guided bike trip. We were never disappointed. Guides, hotels, bikes...



Nov 2023

Written on

life at its fullest

Unlike tours where you gaze at world class natural and historic wonders in another culture, this tour put us in intimate touch with them through cycling, eating, dri...

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Tour Operator

VBT Bicycling Vacations

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Since 1971, VBT has crafted immersive and authentic biking vacations for active travelers. When you travel with VBT, you’re not just another tourist—you’re a traveler. With us, you’ll experience your destination with the help of a local, bilingual trip leader with a passion for sharing their home with you. You’ll eat in local restaurants, stay in accommodations that have been family-owned for generations and cycle through vineyards, olive groves, and medieval villages. 

With VBT, you won’t just visit a place—you’ll immerse yourself in it. You might follow a centuries-old pasta recipe while taking a cooking class in Rome—or learn a folk dance in Croatia, followed by sharing a bottle of locally-produced Grk wine with your new friends. Exploring the world on two wheels lets you experience your surroundings on a deeper level.


VBT offers exceptional value without compromising on quality. Simply put, no other US-based active travel company offers an experience this rich for such a reasonable price. On our tours, you can see more sights, have more local experiences, and enjoy more delicious, authentic meals—all while staying in high-quality, boutique hotels and charming, family-run inns.


All you have to do is show up at the airport—we’ll handle the rest! From tour consultants who help you find the perfect vacation to expert local trip leaders who show you the best place for gelato, we take care of all the little details that make your trip memorable. We book your flights, arrange all your transportation and accommodations, and move your luggage between hotels. Our support vans are available to give you a lift up a hill or quickly fix a flat tire. VBT takes care of your travel details and creates unique itineraries so you can relax and enjoy your small-group vacation from start to finish.


Friendly camaraderie, cultural immersion, and casual comforts are the hallmarks of our vacations. Discover delightful people, beautiful hotels, foreign cultures, and fascinating lifestyles that will enrich your life and provide memories for years to come.

Why we love this operator
Their unique emphasis on immersive cultural experiences combined with active exploration with personalized cycling experiences.
What they’re known for
VBT Cycling are renowned for offering exceptional guided and self-guided bicycle tours worldwide.


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,5 nights in historic antebellum inns
Travel Insurance
We strongly recommend purchasing travel insurance alongside your travel package to safeguard against unforeseen circumstances such as medical expenses, trip cancellations, and other contingencies. It offers you peace of mind and ensures you are prepared for unexpected events that may occur before or during your journey
Visa requirements
Visa requirements vary depending on your country of origin and your country of destination. It is your responsibility to familiarize yourself with the relevant requirements. For a handy tool that can help you quickly find the requirements, please visit this link .
Meals Included

11 meals: 5 breakfasts, 3 lunches, 3 dinners

Age Requirements
13 to 80 years
Additional Information
This tour features easy terrain mixed with some rolling hills (most notably on Day 3, inside Vicksburg National Military Park). Our VBT support vehicle is always available for those who would like assistance. This trip is ideal for both beginning and experienced cyclists. Daily Mileage: 4 - 43 miles| Biking: 2 - 4 hours| Group Size: 20
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