Mississippi: The Natchez Trace

Your 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 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.

From 1:00 to 3:30 p.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, which takes 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 your arrival.

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

After a hearty breakfast, you’ll set off on 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. Traversing lands belonging 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 over 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 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 by the boll weevil epidemic, which devastated the cotton fields of local farmers at the turn of the 20th century. Residents abandoned the beleaguered town, and the last store in Rocky Springs closed its doors in the 1930s. 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.

Hotels: Duff Green Mansion, Anchuca Mansion
Meals: Breakfast, Lunch, Dinner
Daily Options: 18 or 39 miles

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, enjoy dinner on your own in Vicksburg.

Hotels: Duff Green Mansion, Anchuca Mansion
Meals: Breakfast, Lunch
Daily Options: 18 miles

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. 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: Breakfast, Lunch
Daily Options: 22 or 42 miles

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: Breakfast, Dinner
Daily Options: 12 and 36 miles

Your tour concludes after breakfast. VBT’s complimentary shuttle will take 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: 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 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.

From 1:00 to 3:30 p.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, which takes 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 your arrival.

Hotel: Fairview Inn
Meals: Dinner

Today’s Ride Choice:
Jackson Warm-Up: 3 miles

What to Expect: Pass beautiful homes in a historic district on an easy warm-up ride.

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 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, 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 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.

Hotels: Duff Green Mansion, Anchuca Mansion
Meals: Breakfast, Lunch, Dinner

Today’s Ride Choices:
Cumulative Distance Range: 18 – 39 miles

Morning
Rocky Springs to Port Gibson: 18 miles

Afternoon
Port Gibson to Windsor Ruins: 21 miles

What to Expect: Cycle over gentle hills from Rocky Springs to Port Gibson. Wildlife is abundant along your route. Those who would like to continue cycling after lunch can ride to the ruins of Windsor Plantation and back.

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, enjoy dinner on your own in Vicksburg.

Hotels: Duff Green Mansion, Anchuca Mansion
Meals: Breakfast, Lunch

Today’s Ride Choice:
Cumulative Distance Range: 18 miles

Morning
Vicksburg: 18 miles

What to Expect: Enjoy a ride through the park today. The park has two options that will add 5 miles. The Southern Loop Option adds 3 miles with more monuments dedicated to the Confederate States. Grant’s Headquarters adds 2 miles and passes the monument dedicated to soldiers of African descent.

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. Our ride concludes at Monmouth Historic Inn, a National Historic Landmark. 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: Breakfast, Lunch

Today’s Ride Choice:
Cumulative Distance Range: 42 miles

Vicksburg to Natchez: 42 miles

What to Expect: You ride into Natchez, the terminus of the parkway. Passing many sites to visit, you will stop at Coles Creek to enjoy one final picnic lunch prepared by your Trip Leaders, under the shade trees next to the creek. Continue on to Mount Locust and Emerald Mound before arriving in 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: Breakfast, Dinner

Today’s Ride Choices:
Cumulative Distance Range: 12 – 36 miles

Morning
Antebellum Homes: 12 miles
The Natchez Trace: 24 miles

What to Expect: Ride through the historic district of Natchez on “Pilgrimage” in the morning. Need more cycling? Head back out to the Trace and cycle as far as you wish.

Your Natchez Trace trail tour concludes after breakfast. VBT’s complimentary shuttle will take 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: Breakfast