Mississippi: The Natchez TraceCompelling history and scenic cycling merge seamlessly on this voyage along the Natchez Trace trail. Forged by Native Americans centuries ago, the rehabilitated trail follows a designated bicycle route along the lifeline of the Old South. Explore the fascinating ghost town of Rocky Springs, pausing to absorb its haunting history. A local historian leads you through Vicksburg National Military Park, where you’ll relive the Siege of Vicksburg. Here, storied Civil War battlefields feature reconstructed forts, trenches, and monuments to create an immersive storytelling experience. Guide your own expedition on a “pilgrimage” through the picturesque streets of Natchez, home to the grandest antebellum mansions. All the while, lush forests, fertile farmlands, and mighty Mississippi River views frame your cycling journey, while hearty Southern cooking and old-time hospitality help round out your experience
- 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 Vicksbury National Military Park by bicycle
- Visit the sprawling Emerald Mound, one of the largest Native American ceremonial sites
- Customize your own “Pilgrimage” of Natchez’ stately antebellum homes
What to Expect
This tour features easy terrain mixed with some rolling hills (most notably on Day 3, inside Vicksburg National Military Park). There is some urban and parkway riding, where traffic is accustomed to cyclists. Our VBT van support shuttle is always available for those who would like assistance. This trip is ideal for both beginning and experienced cyclists.
- Daily Mileage: 3 - 25|
- Biking: 2 - 5 hr|
Average High /
Low Temperature (°F):
|5 nights in historic antebellum inns|
|11 meals: 5 breakfasts, 3 lunches, 3 dinners|
|Custom VBT bike and helmet|
|Two local trip leaders|
|Ride with GPS and daily route notes|
|Facilitated cultural experiences|
|Your choice of VBT branded gear for your adventure|
Housed in a Colonial Revival mansion built in 1908, this small, luxury hotel in Jackson’s celebrated Belhaven district is listed on the National Register of Historic Places. Since 1994, the Fairview Inn has been the proud recipient of AAA’s elite Four Diamond award. During your stay, you can unwind with a massage at the onsite spa (advance reservations recommended), stroll through more than an acre of meticulously landscaped herb and flower gardens, or sip a literary-themed cocktail served in the cozy, book-lined Library Lounge. Each of the inn’s 18 rooms is air conditioned and features complimentary wireless Internet access.
Duff Green Mansion
You’ll be stepping into the Civil war era when you arrive at Duff Green Mansion. Learn what daily life was like for Duff and Mary Lake Green as they married, built their home, and welcomed their first child. The home’s ballroom was danced in by Jefferson Davis and Ulysses S. Grant. The Duff Green Mansion is one of only four structures in Vicksburg recognized by the Smithsonian Institution and is a member of Condé Nast/Johansens Recommend Hotels and Inns. Built around 1830, the Greek Revival-style Anchuca Mansion is also listed on the National Register of Historic Places. According to legend, Confederate President Jefferson Davis made one of his last public addresses from the property’s front balcony. Anchuca Mansion has nine guest rooms, four in the main property and four in the adjacent carriage house plus a guest house with three bedrooms. Each is comfortably equipped with air conditioning, private bath, and complimentary wireless Internet access. Duff Green Mansion and Anchuca Mansion are located in Vicksburg’s Historic District, within easy walking distance of each other and many of the city’s restaurants, museums, and other attractions.
Monmouth Historic Inn
Bask in Southern luxury at its finest. Built in 1818, the 26-acre, Tara-like Monmouth Historic Inn features lovely gardens and pergolas, a gazebo, bridge-spanned ponds, and walking trails. This magnificent manse was once owned by U.S. Congressman and Mississippi Governor John Quitman. His dream for Monmouth has been fully realized through the loving and careful restoration of the mansion and the addition of seven other buildings to this historic property. Relax and feel at home amid the quiet elegance of the 29 beautifully appointed rooms and suites. Designated a National Historic Landmark, the inn has earned high praise from the likes of Condé Nast Traveler, The New York Times and Architectural Digest. Take your breakfast in Quitman’s Retreat, meet for drinks in the Quitman Study, and savor “Chef’s Table Dining” during your special farewell dinner.
Guest Reviews 73 out of 79 (92%) of reviewers recommend this tour
Other Tours You'll LoveView Related Tours
Starting from 5 days at
Uncover the beauty of British Columbia during this self-guided bike tour of Vancouver Island, riding coastal routes and rail trails from Victoria to the lake filled Saanich Peninsula forests.
Starting from 6 days at
Make the most of your Vancouver Island bike tour as you cycle, sail, and kayak your way through Canada’s vibrant west coast islands.
Starting from 7 days at
Cycle sprawling cacti-dotted landscapes, explore magnificent mining towns, and soak in mountain backdrops with VBT’s quintessential Arizona bike tour.
Stories From North AmericaView All Stories
Why Québec's Eastern Townships are the Perfect Fall Destination
June 6, 2018
Québec is best known to the world for its busy, bustling cities - particularly Québec City and the ultra-cosmopolitan Montreal. But metropolises like these can sometimes overwhelm visitors and make...Continue Reading
What to Buy at the World's Best Holiday Markets
December 16, 2019
The holiday season is a time of joy for people and families the world over. During the winter months, many VBT destinations play host to festive winter and holiday markets...Continue Reading
Visiting the Volcanic Caldera at Yellowstone National Park
September 13, 2018
Looking for VBT Walking Vacations? All VBT Walking Vacations have moved to our sister company, Country Walkers. The same tours you know and love, plus exciting new itineraries, are available...Continue Reading
Talk to a VBT
Mon – Fri 8:30 a.m. – 6:30 p.m. ETTalk to an Expert
Find your perfect tour and reserve a spot with our easy online booking.Find A Tour