Mississippi: The Natchez Trace

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 stay, you’ll enjoy your first taste of legendary Southern hospitality.

If you’re flying to Mississippi, VBT has arranged a complimentary shuttle from Jackson–Medgar Wiley Evers International Airport to the inn. Shuttle reservations are not required, as the service operates on a “show and go” basis, departing once—at 10:00 a.m.—from the airport. If you arrive after 10:00 a.m., you must arrange your own transportation to the inn at your own expense.

If you are driving to the tour, we recommend parking your vehicle at the Fairview Inn. At the tour’s conclusion, you may return here via the VBT van.

At 11:00 a.m., join your VBT trip leaders and 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 area of Jackson, passing the Eudora Welty House—a National Historic Landmark. The Pulitzer Prize–winning author, known for her novels exploring 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. Lunch is on your own. On your way back to the hotel, take time to admire some of Jackson’s vibrant public art murals.

Later, enjoy a welcome reception at the inn and get to know your fellow travelers. In the evening, accompany your trip leaders for an included dinner at a nearby restaurant.

If you wish to book spa services at the Fairview Inn, VBT recommends making your reservation well in advance of 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 quiet residential streets to the Mississippi Civil Rights and History Museums. On the return, you’ll pass many of the city’s vibrant public art murals.

Cumulative Distance Range: 4 – 9 miles

Included Meals: Dinner

After a hearty Southern breakfast, you’ll shuttle to the starting point of your first memorable ride along the scenic Natchez Trace Parkway. This pastoral route loosely follows the Old Natchez Trace Trail, a nearly 500-mile footpath originally blazed by Native Americans and later used by European settlers to connect Natchez, Mississippi, with Nashville, Tennessee. Traversing lands once belonging to the Natchez, Choctaw, and Chickasaw nations, the historic trace became a vital artery for trade and transportation.

In 1938, the National Park Service assumed management of the area, and construction of the modern Natchez Trace Parkway soon began. Completed over 71 years, the result is a cyclist’s dream: the entire 444-mile, two-lane paved route is a designated bike path—free of stop signs, stoplights, and commercial traffic. With a speed limit of just 50 mph, it’s framed by forests, farmlands, scenic overlooks, and dozens of historic sites.

Begin your ride in Rocky Springs. A 60-minute shuttle brings you to this haunting ghost town, once a thriving community along the Trace. In 1878, yellow fever decimated the population, and the subsequent boll weevil epidemic destroyed the cotton economy. By the 1930s, the last store had closed. Today, the only remaining intact building is the Methodist Church, an antebellum structure built in 1837.

From Rocky Springs, cycle the Natchez Trace Parkway to Port Gibson, the town Union General Ulysses S. Grant famously deemed “too beautiful to burn” during the Civil War’s Siege of Vicksburg. Explore its historic streets and enjoy lunch at a local home.

Afterward, ride to the ruins of Windsor Plantation. Built between 1859 and 1861, Windsor was a grand Greek Revival mansion situated on a 2,600-acre estate. During the Civil War, Confederate soldiers used its rooftop to observe Union movements. Though it survived the war, the mansion burned down in 1890 due to a careless smoker. Today, 23 of its original 29 towering columns remain, along with a portion of its ornate balustrade.

Following your ride to Windsor, shuttle about 40 minutes to Vicksburg, where you’ll stay for the next two nights at two of the town’s finest historic inns: Duff Green Mansion and Anchuca Mansion. After settling in, 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 evocative beauty. From here, cycle along the scenic Old Natchez Trace Trail to the charming town of Port Gibson, where you’ll enjoy lunch in a historic home. Afterward, continue riding to the nearby ruins of Windsor Plantation before shuttling about 40 minutes 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 nation’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, featuring reconstructed forts and trenches. The landscapes are solemnly adorned with more than 1,330 monuments and memorials honoring both Union and Confederate soldiers.

Encompassing over 1,800 acres, the park is marked by rolling hills, making today’s ride the most challenging of your tour. You’ll pause to explore the USS Cairo Museum and get a close-up look at the formidable Union ironclad that, in 1862, became the first ship sunk by a mine. A picnic lunch follows, during which your guide offers deeper insights into the decisive Siege of Vicksburg.

Cycling back to your inn, you may opt to visit the Old Courthouse Museum. This grand antebellum landmark—designated a National Historic Landmark in 1968—houses an eclectic collection of Civil War artifacts, including the tie worn by Confederate President Jefferson Davis at his inauguration.

This evening, enjoy a special southern gospel presentation before dining 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 Vicksburg National Military Park. A local historian guides you through reconstructed battlefields, sharing enriching Civil War history along the way. 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 that houses 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 and scenic ride along the Natchez Trace Parkway.

Today’s ride allows you to set your own pace, pausing to take in the parkway’s striking vistas as you cycle south toward Natchez. You might stroll through the hardwood and pine forests around Bullen Creek, then regroup at Coles Creek for a picnic lunch with your trip leaders. Afterward, explore Mount Locust Inn & Plantation. Built in 1780, Mount Locust was one of the first “stands,” or inns, in Mississippi, offering warm meals and comfortable beds to weary travelers of the Natchez Trace.

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

Continuing on to Natchez, perhaps pause to visit the Elizabeth Female Academy. Opened in 1818, it was the first educational institution exclusively for women in Mississippi—and is believed by many to be the first college in the U.S. to award advanced degrees to women.

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

Tonight, enjoy dinner on your own at one of Natchez’s excellent local restaurants.

Today's Ride Choices

Morning: Port Gibson to Lunch — 24 miles

Afternoon: Lunch to Natchez — 19 miles

What to Expect:

Ride from Port Gibson into Natchez, the southern terminus of the parkway, passing several notable sites along the way. Stop to enjoy one final picnic lunch prepared by your trip leaders beneath the shade of creekside trees. After lunch, continue riding to Mount Locust and Emerald Mound before arriving in Natchez.

Cumulative Distance Range: 19 – 43 miles

Included Meals: Breakfast, Lunch

Natchez is renowned for its Spring Pilgrimage, an annual celebration of the town’s most impressive antebellum homes. The tradition began in 1932, when Katherine Grafton Miller—president of the Natchez Garden Club—was forced to reimagine the club’s spring fundraiser after an unexpected cold snap threatened their garden tours. She proposed inviting visitors inside the city’s stately homes, offering a glimpse of what she called “where the Old South still lives and where shadowed highways and antebellum homes greet old and new friends.” That first Spring Pilgrimage was a resounding success. Guests—many from the North—were driven from house to house and entertained by hoop-skirted hostesses holding parasols. A well-publicized visit from First Lady Eleanor Roosevelt in 1939 further cemented the event’s popularity. Now referred to simply as “Pilgrimage,” it has evolved into a multi-week celebration held each spring and fall. Many of the city’s historic homes also offer guided tours year-round.

Today, you embark on your own Pilgrimage—VBT-style—cycling through Natchez’s picturesque streets, where fragrant magnolia and dogwood trees bloom in the spring. This morning, ride with your small group to Longwood, an unforgettable (and unfinished) octagonal mansion, for a guided tour. Then continue at your own pace, using your included admission to visit one of the city’s grandest antebellum homes, such as Rosalie—renowned for its Federal-style portico and rosewood furnishings—or the Greek Revival-style Stanton Hall.

If you feel parched or peckish, your trip leaders can recommend local favorites. Perhaps stop for a mint julep over lunch at the Magnolia Grill in the historic Natchez Under-the-Hill district. A local favorite, the Grill serves up Southern staples like okra gumbo, crawfish étouffée, and homemade coconut buttermilk pie.

This evening, celebrate your final night in Mississippi with a memorable four-course, candlelit dinner of contemporary Southern cuisine served in the 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” this morning, pausing to explore grand antebellum mansions. If you’re eager for more cycling, head back out to the Natchez Trace Trail and ride as far as you wish. An additional independent route may also be available 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 by noon. We recommend scheduling your flight home no earlier than 1:00 p.m. Guests needing to reach the airport earlier or later must make their own transportation arrangements.

Included Meals: Breakfast

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, your trip leaders can assist in selecting one of the town’s eateries. You may wish to stop and savor a mint julep over lunch at the Magnolia Grill, located in the historic Natchez Under-the-Hill district. The Magnolia Grill is the local choice for Southern culinary staples like okra gumbo, crawfish etouffée, and homemade coconut buttermilk pie.

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