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Mississippi: The Natchez Trace

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.

Tour Highlights

  • 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’ stately antebellum homes.

Positive Impact

VBT is proud to support Wine to Water with a donation on behalf of each guest on this tour. Wine to Water is an international organization providing access to clean drinking water and emergency supplies in water-challenged regions. We believe in giving back to the places that have enriched the lives of our guests. We’re committed to identifying and supporting sustainable initiatives in a variety of areas including education, world health, economic equality, safe drinking water, the environment, and the preservation of cultural traditions.

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 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
Activity Easy/Moderate
Bar Graph Beginner - Experienced
Vehicle Support Vehicle

Average High /
Low Temperature (°F):








Mar6.4 in

Apr5.5 in

May5.5 in

Sep3.36 in

Oct3.8 in

Nov5.1 in

Tour Only

5 nights in historic antebellum inns


11 meals: 5 breakfasts, 3 lunches, 3 dinners


Transportation from Jackson-Evers Airport to the Fairview Inn in Jackson


Transportation from Natchez to Jackson-Evers Airport or the Fairview Inn in Jackson

2025 2024

Electric-Assisted Bicycle (E-bike)

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Road Bicycle (Aluminum alloy frame)

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Step-Through (Mixte Hybrid) Comfort Bicycle

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Step-Over (Diamond) Comfort Bicycle

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2025 2024

Electric-Assisted Bicycle (E-bike)

See More >

Road Bicycle (Aluminum alloy frame)

See More >

Step-Through (Mixte Hybrid) Comfort Bicycle

See More >

Step-Over (Diamond) Comfort Bicycle

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Biking Packages Include:

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


Sun, Mar 23 to Fri, Mar 28, 2025

Show Itinerary:

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 to Mississippi, VBT has arranged for a complimentary shuttle to take 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 10:00 a.m.  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.

At 11:00 a.m., join 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 leads you through a primarily residential neighborhood of Jackson, passing the Eudora Welty House, a National Historic Landmark. The Pulitzer Prize-winning author, celebrated for her novels highlighting the Southern experience, lived and wrote here from 1925 until her death in 2001. This morning’s ride ends at the Mississippi Civil Rights Museum, which you may choose to visit. Stop for lunch on your own. As you return to the hotel, stop to view some of the city’s public art murals. Later, get to know your fellow travelers during a welcome reception at the inn. Then you’ll venture out with your 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 your arrival.

Today's Ride Choices

Morning: Fairview to Museum Warm-up Ride — 4 miles

Afternoon: Museum to Fairview Warm-up Ride — 5 miles

What to Expect:

A short warm-up ride takes you along Jackson’s homey residential streets to visit the Mississippi Civil Rights and History Museums. On the return journey, pass many of the city’s public art murals.

Cumulative Distance Range: 4 – 9 miles

Included Meals: Dinner

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 several centuries ago and connecting Natchez, Mississippi, with Nashville, Tennessee. Traversing lands belonging to the Natchez, Choctaw, 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 Trail. 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 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 and enjoy lunch at a historic home in Port Gibson.

After lunch, cycle to the ruins of nearby Windsor Plantation. 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.

Following your ride to Windsor, you’ll shuttle (about 40 minutes) to Vicksburg, where you stay for the next two nights. Your group will stay in two of the town’s finest historic inns: Duff Green Mansion and Anchuca Mansion. After settling in, you gather for dinner at Anchuca Mansion.

Today's Ride Choices

Morning: Rocky Springs to Port Gibson — 19 miles

Afternoon: Port Gibson to Windsor — 21 miles

What to Expect:

An hour-long shuttle brings you to the haunting ghost town of Rocky Springs, where you’ll pause to explore its eerie beauty. From here, continue along the scenic Old Natchez Trace Trail. Cycle to the beautiful town of Port Gibson, where you’ll enjoy lunch in a historic home. Afterward, ride to the ruins of nearby Windsor Plantation before your 40-minute shuttle to Vicksburg.

Cumulative Distance Range: 19 – 40 miles

Included Meals: Breakfast, Lunch, Dinner

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 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, you will be treated to a wonderful southern gospel presentation before enjoying dinner on your own in Vicksburg.

Today's Ride Choices

Morning: Vicksburg — 17 miles

What to Expect:

A scenic ride out of Vicksburg leads you to the Vicksburg National Military Park. A local historian guides you through recreated battlefields, relaying enriching Civil War history. Pause to explore the USS Cairo Museum and enjoy a picnic lunch. Later, you may choose to visit the Old Courthouse Museum, a National Historic Landmark housing an impressive collection of Civil War artifacts.

Cumulative Distance Range: 17 miles

Included Meals: Breakfast, Lunch

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 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. Your ride concludes at Monmouth Historic Inn, a National Historic Landmark. You’ll stay here for the next two nights. Indulge in a few games of croquet or take a relaxing stroll through the property’s expansive gardens at your leisure.

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

Today's Ride Choices

Morning: Port Gibson to Lunch — 24 miles

Afternoon: Lunch to Natchez — 19 miles

What to Expect:

You ride from Port Gibson into Natchez, the terminus of the parkway, passing many sites you may visit at your leisure. Along the way, stop to enjoy one final picnic lunch prepared by your trip leaders, under the shade trees next to the creek. After lunch, continue on to Mount Locust and Emerald Mound before arriving in Natchez.

Cumulative Distance Range: 19 – 43 miles

Included Meals: Breakfast, Lunch

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 with your small group 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 a guided tour 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.

Today's Ride Choices

Morning: Antebellum Pilgrimage — 13 miles

Afternoon: The Natchez Trace — 24 miles

What to Expect:

Ride through the historic district of Natchez on “Pilgrimage” in the morning, where you’ll explore grand antebellum mansions. Need more cycling? Head back out to the Natchez Trace Trail and cycle as far as you wish.

Today may offer an additional independent ride for experienced cyclists. Ask your trip leader for details

Cumulative Distance Range: 13 – 37 miles

Included Meals: Breakfast, Dinner

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 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. Guests who need to get to the airport earlier or later must make their own arrangements.

Included Meals: Breakfast

Mississippi: The Natchez Trace

Download PDF Itinerary:

Tour Only (PDF)


120 out of 125 (96%)
4.7 out of 5 stars.
Read More Reviews

The Natchez Trace Tour consisted of five days of biking at an easy pace on the Natchez Trace Parkway. The Parkway with its excellent paved surface, light, non-commercial traffic, and a speed limit of 50 mph provided a safe and relaxing biking trail of undulating hills. We travelled through beautiful forests and farmland, with opportunities to take in some of the history of the Trace. The stays in the antebellum inns were delightful with large, well-appointed rooms and excellent dining. During our stays in Vicksburg and Natchez, we learned about the Civil War battles in this area and about the era of cotton plantations. The tour provided exercise, history and good food with attentive guides.

Strawberry12, Halifax, NS, Canada

This tour was a wonderful combination of exercise and relaxation.

This VBT trip exceeded expectations. The mansions we stayed in were stunningly beautiful, and the rides along the Natchez Trace were lovely and well paced. Of special note, was the day riding through the Vicksburg National Park and seeing all the monuments and learning about the battle of Vicksburg. The guides and extra activities were marvelous, as were the meals and friendly folks we rode with and met along the trail.

Cricket Weston, Charlotte, NC

Southern Charm and History Abounds

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