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Mississippi: The Natchez Trace

National Parks

Rolling seamlessly from Mississippi to Tennessee, the Natchez Trace has long been a vital conduit for Southern pride—and a paradise for cyclists. You’ll experience that pride firsthand as you visit Civil War battlefields in the company of a Southern historian, explore elegant antebellum mansions, and pause to admire spectacular landscapes and manicured gardens. You’ll also experience the hearty cuisine and gracious hospitality of the South at some of the finest inns in the land. Our flexible itinerary allows you to take it all in at your own pace.

  • Activity Level: Easy / Moderate
  • Daily Mileage: 15 - 49 mi
  • Daily Biking: 2 - 5 hr
  • Small Groups: 20
  • Biking Activity
  • Ideal for energetic beginners to more experienced riders.

Why You'll Love This Tour


Mississippi: The Natchez Trace Bike Vacation

Cultural Highlights

  • Enjoy 5 unforgettable nights in charming and historic antebellum inns
  • Cycle through timeless architectural districts filled with Southern landmarks
  • Discover Port Gibson, declared “too beautiful to burn” by General Grant
  • Explore the pastoral Natchez Trace Parkway, the nation’s longest designated bike path
  • Evoke a long-gone era at the 2,600-acre Windsor Ruins
  • Cycle historic Vicksburg National Military Park with its vivid monuments
  • Share a cozy picnic lunch with your Trip Leaders and fellow travelers
  • Set your own pace as you cycle south toward Natchez
  • Stroll through the shaded hardwood forest by Bullen Creek
  • Admire the magnolia- and dogwood-lined streets of Natchez on a cycling Pilgrimage

What to Expect

This tour features easy terrain mixed with some rolling hills (most notably on Day 3, inside Vicksburg National Military Park). Our VBT van support shuttle is always available for those who need assistance. This trip is ideal for both beginning and experienced cyclists.

Average Daily Mileage: 15 – 25 miles
Average Cycling Time: 2 – 5 hours

Climate Information

Average High/Low Temperature (°F) – Vicksburg
Mar 72°/45°  Apr 78°/52°  May 84°/61°  Sep 88°/65°  Oct 79°/64°  Nov 69°/45°

Average Rainfall (in.) – Vicksburg
Mar 6.8  Apr 5.6  May 5.4  Sep 3.3  Oct 3.8  Nov 5.0

What’s Included:

  • 5 nights in historic, antebellum inns
  • 11 meals – 5 breakfasts, 3 lunches, 3 dinners
  • FREE use of our custom VBT bicycle and helmet
  • Service of two VBT Trip Leaders
  • Daily route directions and maps
  • Welcome reception
  • Sightseeing and cultural activities
  • Transfers
  • Guided tour of the Vicksburg National Military Park
  • 4-course candlelight dinner at Monmouth Historic Inn
  • Tour of the USS Cairo Museum
  • Guided tours of three antebellum homes in Natchez
  • 5% Frequent Traveler Credit to use on your next VBT vacation. See details.

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Land Only Single Supplement: $545

Please note: Web Special savings cannot be combined with any other offer. Standard Terms & Conditions apply when purchasing this trip. Ask our Tour Consultants for details. Every effort has been made to produce this information accurately. We reserve the right to correct errors. Prices are based on preferences selected above, including meals and sightseeing as specified in What’s Included. All prices are subject to change. Departure dates and prices shown may be updated several times daily, and apply to new bookings only.

Itinerary & Map
Or, Expand All Days
Day 1: Arrive in Jackson / Warm-up ride / Welcome reception and dinner

Your tour begins at the Fairview Inn in Jackson, where you stay for one night and enjoy your first taste of legendary Southern hospitality.

If you’re flying to Mississippi, VBT has arranged for a complimentary shuttle to bring you from Jackson-Evers International Airport to the inn. Shuttle reservations are not required, as the shuttle works on a “show and go” basis, and will make its only departure from the airport at 2:00 p.m. Meet the driver, who will be holding a VBT sign, in the baggage claim area on the ground floor. There will also be a chauffeur in the third lane as you exit the airport from the baggage claim area. He will also be holding a VBT sign. If you are scheduled to arrive at the airport after 2:00 p.m., or if you are delayed, you must take a taxi to the inn at your own expense.

If you are driving to the tour, we recommend that you park your vehicle at the Fairview Inn. You may return to the inn at the end of the tour by way of the VBT van. If you are delayed, or your travel plans change, please contact the Fairview Inn; they will inform your VBT Trip Leaders.

At 3:30 p.m., meet your VBT Trip Leaders and your fellow travelers at the inn for a safety briefing and bike-fitting session, followed by a short warm-up ride. Your route, which brings you through a primarily residential neighborhood of Jackson, leads you past the Eudora Welty House, a National Historic Landmark, at 1119 Pinehurst Street. The Pulitzer Prize-winning author, celebrated for her novels highlighting the Southern experience, lived and wrote here from 1925 until her death in 2001.

Later, get to know your fellow travelers during a welcome reception at the inn. Then you’ll venture out with our Trip Leaders for an included dinner at a nearby restaurant.

If you wish to enjoy the Fairview Inn’s spa services during your stay, VBT encourages you to make your reservations well in advance of our arrival.

Hotel: Fairview Inn
Meals: D
Daily Options: 3 miles

Day 2: Rocky Springs / Natchez Trace Parkway / Vicksburg

After a hearty Southern breakfast, you’ll set off to begin what is sure to be a memorable ride along the scenic Natchez Trace Parkway.

This pastoral parkway loosely follows the Old Natchez Trace, a nearly 500-mile footpath blazed by Native Americans several centuries ago and connecting Natchez, Mississippi, with Nashville, Tennessee. Traversing lands belonging the Natchez, Choctow, and Chickasaw nations, this historic route became a vital artery for transportation and trade. In 1938, the area came under the management of the National Park Service, and construction of the modern Natchez Trace Parkway began soon after. It took more than 71 years to complete, but the end result was well worth the wait, especially for cyclists: The entire 444-mile-long, two-lane paved parkway is a designated bike path; has no stop signs or stop lights (and, thus, no cross-traffic); is off-limits to commercial vehicles; features a speed limit of just 50 mph; and is framed by lush forests, fertile farmlands, scenic overlooks, and scores of historic sites.

Begin your ride in Rocky Springs. A shuttle (about 60 minutes) brings you to the haunting ghost town, once a thriving community on the Old Natchez Trace. In 1878, however, the town’s population was decimated by an outbreak of yellow fever, a tragedy compounded further by the boll weevil epidemic, which devastated the cotton fields of local farmers at the turn of the 20th century. One by one, residents abandoned the beleaguered town, and the last store in Rocky Springs closed its doors in the 1930s. Today, one of the only remaining intact buildings is the Methodist Church, an antebellum structure dating back to 1837.

Leaving Rocky Springs, you cycle along the Natchez Trace Parkway to Port Gibson, the town that Union General Ulysses S. Grant famously declared “too beautiful to burn” during the Civil War’s infamous Siege of Vicksburg. Alight here to explore the historic town, as well as the nearby Windsor Ruins. Built between 1859 and 1861, Windsor was an opulent Greek Revival mansion set on a sprawling plantation spanning more than 2,600 acres. During the Civil War, the four-story property’s expansive rooftop was used by Confederate soldiers to observe the movements of Union troops. Although Windsor survived the Civil War intact, irony lent a merciless hand in 1890, when the mansion burned to the ground during a fire started by a careless smoker. Today, all that remains of the once-magnificent property are 23 of the original 29 columns, each 45 feet tall, and a portion of the elaborate balustrade that once connected them.

After lunch in Port Gibson, you’ll shuttle north (about 40 minutes) to Vicksburg where you stay for the next two nights. Your group will be staying in two of the town’s finest historic inns: Duff Green Mansion and Anchuca Mansion. Both properties are located in the city’s Historic District, so you’ll savor every moment no matter which one you call home. After settling in, you gather for dinner at Anchuca Mansion.

Hotels: Duff Green Mansion, Anchuca Mansion
Meals: B, L, D
Daily Options: 18 or 39 miles

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’s Center to watch a short documentary film, then join a local historian for a guided tour of the park’s historic battlefields, which feature reconstructed forts and trenches. The battlefields are solemnly dressed by more than 1,330 monuments and memorials to both Union and Confederate soldiers.

Encompassing more than 1,800 acres, the park is rife with rolling hills, making today’s ride the most challenging of your tour. You’ll alight to explore the USS Cairo Museum, enjoying a closer look at the formidable Union ironclad, which in 1862 became the first ship to be sunk by a mine. You’ll also pause for a picnic lunch, during which your local guide offers more Civil War insights, chronicling the decisive Siege of Vicksburg.

Cycling back to your inn, you may choose to visit the Old Courthouse Museum. This impressive and imposing antebellum building, which was named a National Historic Landmark in 1968, houses an eclectic array of Civil War artifacts—including the tie that Confederate President Jefferson Davis wore to his inauguration—many of which were donated by local residents.

Tonight, enjoy dinner on your own in Vicksburg.

Hotels: Duff Green Mansion, Anchuca Mansion
Meals: B, L
Daily Options: 12.5 or 17.5 miles

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 Parkway.

You’ll have the opportunity to set your own pace today, stopping to take in the parkway’s striking vistas as you cycle south toward Natchez. For example, you might pause for a stroll through the hardwood and pine forests around Bullen Creek. Regroup at Coles Creek for a picnic lunch with your Trip Leaders, then explore the Mount Locust Inn & Plantation. Built in 1780, Mount Locust was one of the first “stands,” or inns, in Mississippi, providing warm meals and comfortable beds to weary Natchez Trace travelers.

Next, you pedal to Emerald Mound, one of the largest Native American ceremonial mounds in North America. Believed to have been built and consecrated by ancestors of the Natchez Indians between the 14th and 16th centuries, Emerald Mound covers an area of more than eight square acres and boasts a carefully constructed flattened plateau rising more than 35 feet. It was designated a National Historic Landmark in 1989.

Continuing on to Natchez, perhaps you’ll pause to visit the Elizabeth Female Academy. Opened in 1818, it was the first educational institution exclusively for women in the state of Mississippi—and, many believe, the first college in the United States to award women advanced degrees. Our ride concludes at Monmouth Historic Inn, a National Historic Landmark and proud recipient of AAA’s elite Four Diamond rating for more than 30 years. You’ll stay here for the next two nights, perhaps indulging in a few games of croquet or a taking a relaxing stroll through the property’s expansive gardens during your leisure time.

You’ll find a number of excellent options for dinner on your own in town tonight

Hotel: Monmouth Historic Inn
Meals: B, L
Daily Options: 22 or 41 miles

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 fundraiser: guided tours of members’ lushly landscaped, magnolia-, azalea-, and camellia-filled gardens. Deciding to bring visitors inside the stately homes, Miller envisioned the event as an opportunity for others to see “where the Old South still lives and where shadowed highways and antebellum homes greet old and new friends.” Visitors, many of whom hailed from the north, were personally driven from home to home and regaled with tales told by ladies wearing hoop skirts and holding parasols. The first Spring Pilgrimage in 1932 was a resounding success, and a well-publicized visit by First Lady Eleanor Roosevelt in 1939 further cemented the tradition, which continues to this day. Now referred to simply as “Pilgrimage,” it has grown into a multi-week event, occurring in both spring and fall. What’s more, many of the city’s historic homes offer guided visits year-round.

Today, you mount your own Pilgrimage, VBT-style, cycling through the picturesque streets of Natchez, which in spring are lined with fragrant magnolia and dogwood trees. This morning, you will cycle together to Longwood, an unforgettable (and unfinished) property featuring a unique octagonal design, for a tour together.  Then you can set your own pace, pausing when you like to take advantage of your included admission to another of the city’s grandest antebellum homes, all of which are designated National Historic Landmarks. Enjoy guided tours of Rosalie, known for its Federal-style columned portico and ornate rosewood furniture, or Greek Revival-style Stanton Hall.

Should you feel parched, you may wish to stop and savor a mint julep over lunch at the Carriage House Restaurant, located on the grounds of Stanton Hall. The Carriage House is the locals’ choice for Southern culinary staples like fried chicken, buttermilk biscuits, and warm pecan cobbler.

On the last night of your stay in Mississippi, you’ll be treated to a memorable four-course, candlelit dinner of contemporary Southern cuisine in our inn’s acclaimed dining room.

Hotel: Monmouth Historic Inn
Meals: B, D
Daily Options: 12 or 23 miles

Day 6: Depart for home

Your tour concludes after breakfast. VBT’s complimentary shuttle will bring you to either Jackson-Evers International Airport or to the Fairview Inn in Jackson. The shuttle departs Natchez at 9:00 a.m., arriving at the airport around 11:30 a.m. and at the inn at noon. We suggest you schedule your flight home no earlier than 1:00 p.m.

Meals: B

Mississippi: The Natchez Trace Map

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Duff Green Mansion, Anchuca 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 Conde 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 Historical District, within easy walking distance of each other and many of the city’s restaurants, museums, and other attractions.
Free WiFi Included

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. A/C is available.
Free WiFi Included

Fairview Inn

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 on-site 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.
Free WiFi Included

Mississippi Bike Tour Photo Gallery
Click here to view traveler submitted photos

  • Longwood driveway biking
  • Clinton Overlook
  • Vicksburg
  • Vicksburg
  • USS Cairo
  • The Old Trace
  • Stanton Hall
  • National Cemetery Vicksburg
  • Natchez Trace Parkway
  • Natchez Trace Parkway bikers
  • Natchez homes
  • Longwood Mansion
  • Natchez Basilica
  • Longwood Drive
  • Isabellas Port Gibson
  • Isabellas Port Gibson Lunch

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