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Mississippi: The Natchez Trace

The historic Natchez Trace—carved through the wilderness by Native Americans, expanded by pioneer settlers, and now enjoyed by bicyclists— is the best way to discover the exceptional beauty and historical importance of a part of Mississippi steeped in American history.

  • Activity Level: Easy / Moderate
  • Daily Mileage: 15 - 49 mi
  • Daily Biking: 2 - 5 hr
  • Small Groups: 20
  • Biking
  • Easy / Moderate

Why You'll Love This Tour


Mississippi: The Natchez Trace

Turn back the hands of time and immerse yourself in the rich history and captivating culture of the American South. Pedaling along the famed Natchez Trace Parkway—once a rugged trail blazed by Native Americans and pioneer settlers, now a pastoral pathway flanked by lush forests, fertile farmlands, and scenic overlooks—we’ll stop to explore now-tranquil fields that witnessed fierce Civil War battles and imposing antebellum homes that recall the splendor of a bygone era. We’ll also experience the region’s legendary hospitality with a memorable horse-drawn carriage ride, sumptuous five-course candlelight dinner, and rejuvenating stays in intimate, historic inns.

Cultural Highlights

  • Pedal past lush, tranquil landscapes on the idyllic Natchez Trace Parkway
  • Explore Vicksburg National Military Park’s hallowed battlefields and poignant monuments with a local historian
  • Discover the USS Cairo, a Civil War ironclad that in 1862 became the first ship sunk by a mine
  • Behold Emerald Mound, one of the largest Native American ceremonial mounds on the continent
  • Partake in the Natchez tradition known as “Pilgrimage,” with guided tours of three stately antebellum homes
  • Climb aboard a horse-drawn carriage for an unforgettable evening ride in Natchez
  • Savor a delectable, five-course candlelight dinner at the award-winning Monmouth Historic Inn
  • Experience true Southern hospitality with relaxing stays in historic antebellum inns

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: 15-49 miles
Average Cycling Time: 2-5 hours

Climate Information

Average Daily Temperature (°F) – Vicksburg
Mar 71°  Apr 78°  May 84°  Sep 87°  Oct 80°  Nov 70°

Average Rainfall (in.) – Vicksburg
Mar 6.4  Apr 5.5  May 5.5  Sep 3.7  Oct 3.8  Nov 5.1

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
  • 5-course candlelight dinner at Monmouth Plantation
  • Tour of the USS Cairo, a Union gunboat sunk by a mine
  • Entrance into three of Natchez's antebellum homes for guided tours
  • 5% Frequent Traveler Credit to use on your next VBT vacation
  • Special Good Buy Discount
Dates & Prices

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Land Only Single Supplement: $445

Please note: Web Special savings cannot be combined with any other offer. Standard Terms & Conditions apply when purchasing this trip. 2015 Prices include all airline surcharges and Government taxes and fees. 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 Jackson / Warm-up ride / Welcome reception and dinner

Make your own arrangements for travel to the Fairview Inn, where we stay for one night and enjoy our first taste of the 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 pm. 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. They will also be holding a VBT sign. If you are scheduled to arrive at the airport after 2:00 pm, 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 pm, 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. Our route, which brings us through a primarily residential neighborhood of Jackson, brings us 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, we’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 / Vicksburg

After a hearty Southern breakfast, we’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 Parks 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.

We’ll begin our ride in Rocky Springs. A shuttle (approximately 60 minutes) brings us 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, we cycle along the Natchez Trace Parkway to Port Gibson, the town Union General Ulysses S. Grant famously declared “too beautiful to burn” during the Civil War’s infamous Siege of Vicksburg. We’ll 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 at a restaurant in Port Gibson, we’ll shuttle to Vicksburg, where we stay for the next two nights. Our group will be staying in two of the town’s finest historic inns: Baer House Inn 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, we gather for dinner together at Anchuca Mansion.

Hotels: Baer House Inn, Anchuca Mansion
Meals: B, L, D
Daily Options: 20 or 41 miles

DAY 3: Vicksburg Battlefield loop

Riding out from our inns today, we cycle through Vicksburg and past scenic overlooks of the Mississippi River. Our destination is Vicksburg National Military Park, home to the country’s largest Civil War cemetery. We 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 and are punctuated 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 our tour. We’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. We’ll also pause for a picnic lunch, during which our local guide offers more Civil War insights, chronicling the decisive Siege of Vicksburg.

Cycling back to our inns, you may choose to visit the Old Courthouse Museum. The 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 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: Baer House Inn, Anchuca Mansion
Meals: B, L
Daily Options: 15 or 20 miles

DAY 4: Natchez Trace Parkway / Emerald Mound

After breakfast, we’ll return via shuttle to Port Gibson, where we’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 we cycle south toward Natchez. For example, you might pause for a stroll through the hardwood pine forests around Bullen Creek. We’ll regroup at Coles Creek for a picnic lunch with our Trip Leaders, then explore the Mount Locust Inn & Plantation. Built in 1780, Mount Locust was one of the first “stands,” or inns, in Mississippi, and provided warm meals and comfortable beds to weary Natchez Trace travelers.

Next, we 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 the Monmouth Historic Inn, a National Historic Landmark and proud recipient of AAA’s elite Four Diamond rating for more than 30 years. We’ll stay here for the next two nights, perhaps indulging in a few games of croquet or a relaxing stroll through the property’s expansive gardens during our leisure time.

Tonight, horse-drawn carriages carry us through town, where we’ll find a number of excellent options for dinner on our own.

Hotel: Monmouth Historic Inn
Meals: B, L
Daily Options: 23 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 today. 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, we mount our own Pilgrimage, VBT-style, cycling through the picturesque streets of Natchez, which in spring are lined with fragrant magnolia and dogwood trees. You can set your own pace, pausing when you like to take advantage of your included admission to three 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; Greek Revival-style Stanton Hall; and Longwood, an unforgettable (and unfinished) property featuring a unique octagonal design.

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 our stay in Mississippi, we’ll be treated to a memorable five-course, candlelight dinner of contemporary Southern cuisine in our inn’s acclaimed dining room.

Hotel: Monmouth Historic Inn
Meals: B, D
Daily Options: 10 or 33 miles

DAY 6: Depart for home

Our 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 am, arriving at the airport around 11:30 am and at the inn at 12:00 pm. We suggest you schedule your flight home no earlier than 1:00 pm.

Meals: B

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Baer House Inn and Anchuca Mansion

Listed on the National Register of Historic Places, the Baer House Inn was originally a residential home built in 1870. Considered one of the finest examples of Eastlake Victorian architecture in Mississippi, the property’s seven guest rooms are decorated with period furnishings—and feature modern amenities such as king- and queen-sized beds, and complimentary wireless Internet access. 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 seven guest rooms, three in the main property and four in the adjacent carriage house. Each is comfortably equipped with air conditioning, private baths, and complimentary wireless Internet access. Both Baer House Inn 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 State 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 on this historic property. Relax and feel at home amid the quiet elegance of the 29 beautifully appointed rooms and suites. This National Historic Landmark has earned 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 our special farewell dinner.
Free WiFi Included

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