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Natchez Trace

  • Natchez Trace
  • Natchez Trace ruin site
  • Armadillo Natchez Trace
  • Fairview Inn guest pantry
  • Fairview Inn with van
  • Natchez Trace Fall
DURATION
6 Day(s)
DAILY BIKING
20 to 30 miles
TRIP DIFFICULTY
1-Easier
STARTING FROM
$2295
SINGLES FROM
$500

Trip Overview

Our Natchez Trace tour is a perfect late-season or early-season biking destination on quiet roads — with added bonuses for history buffs. Enjoy famous southern hospitality, trees festooned with Spanish moss, and views of the mighty Mississippi River. The Natchez Trace Parkway is a restricted-access road with no commercial traffic built by the U.S. Park Service in the 1930s to honor this historic trail and road. The Trace figures prominently as a pathway in local American Indian history — from the mound-building societies beginning as early as the first century A.D. to the shrinking territories of the Chickasaw and Creek tribes prior to the Trail of Tears. In the early 1800s, boatmen floated goods down the Ohio and Mississippi rivers to Natchez, Mississippi, where their boats were sold for lumber. Then they made an over 400-mile trek back to the Ohio Valley on the Natchez Trace. This corridor has been preserved, and now it’s one of the premier cycling destinations in the U.S. You cycle most of the southern one-third of this 444-mile parkway — and visit fascinating rural historical plantations and ruins. Enjoy two nights in Natchez, MS, and one at an inn situated in a wildlife refuge. The final two nights are in Jackson, MS, where you ride more of the Natchez Trace and visit the Mississippi Civil Rights Museum. You experience rural life, delicious southern cooking and historical landmarks on this iconic bicycle tour.

Itinerary

From start to finish, check out the route.

DAY 1 - Arrival Day
Distance: 20 or 40 miles | Terrain: Easier | The Monmouth Historic Inn and Gardens
Meet your leaders at the Home 2 Suites in Ridgeland, Mississippi, at 9 a.m. on Sunday, and head out on the Natchez Trace Parkway for your first ride. As you pass through Clinton, stop by the visitor center museum highlighting the history of the Trace and of Clinton. As you continue south, you see the historic location of the Battle of Raymond, where General Ulysses S. Grant’s troops clashed with the confederate brigade of General John Gregg on May 8, 1863. Pedal through history at Dean’s Stand where General Grant made his headquarters after the Battle of Raymond. And see Red Bluff Stand, which previously served as the boundary between the Choctaw tribe and three different nations: France, Spain, and the U.S. A picnic lunch is included. Finish the day with a walk to Rocky Springs, an abandoned town from the late 1800s. Then shuttle to Natchez for your first night in Mississippi’s oldest town — with dinner at our historic hotel, the Monmouth Inn. This exquisite inn was built in 1818 and is listed as a National Historic Landmark.
DAY 2 - Natchez Trace Parkway Ride
Distance: 30 or 50 Miles | Terrain: Easier | The Monmouth Historic Inn and Gardens
Today you explore Natchez and the surrounding countryside. After taking time to tour Monmouth Inn, you cycle to sites preserved by the National Park Service and others — including the Melrose Estate, which was one of the first plantation-style estates built inside a southern city. You also ride through Natchez and the historic riverfront area, where you may choose to stop for lunch. Lunch is on your own with suggested options. If you’re looking for longer miles, you can also do an out-and-back ride on the southern end of the Trace. This is the Deep South! Spanish moss hangs from the trees, and the scenery varies from hardwood forest to open pastures and cotton fields. Dinner tonight is on your own, with a wide variety of restaurants to choose from in Natchez.
DAY 3 - Emerald Mound & Windsor Ruins
Distance: 20 or 50 miles | Terrain: Easier | Canemount Plantation Inn
Head north this morning on the Natchez Trace and then onto rural side roads. Explore some of the historical artifacts along the Trace, including Emerald Mound — the second largest Indian mound site in the U.S. Ride past Alcorn State University, founded in 1871 by the Reconstruction-era legislature to provide higher education to freedmen. A picnic lunch is included. Along the route, visit the Windsor Ruins — built in the mid-1850s — a plantation that once sprawled over 2,600 acres, which now appears like a Roman ruin, thanks to the 23 still-standing columns. Your home for the night is the Canemount Plantation Inn, a historic 1850s house and grounds that have recently been converted into a B&B. Dinner is at the inn.
DAY 4 - Sunken Trace
Distance: 25 or 40 miles | Terrain: Easier | Fairview Inn
The riding today brings you farther north along the Natchez Trace back toward Jackson. See the charming town of Port Gibson and enjoy the quiet scenery on the way back to Rocky Springs. You also visit the Sunken Trace, a preserved section of the original route, where you can easily imagine a lone horseman appearing around the bend on his arduous wilderness journey. A picnic lunch is included. End the day at the edge of Jackson, with a short shuttle to the most elegant Inn in town. Relax and enjoy the privacy of this small, stately inn or explore town in late afternoon and visit sites such as the Eudora Welty Museum. Dinner tonight is on your own in Jackson, with many choices available. (On the April 19-24, 2020, tour departure, we instead stay at the Old Capitol Inn in Ridgeland.)
DAY 5 - Scenic Ross Barnett Reservoir
Distance: 30 to 60 miles | Terrain: Easier | Fairview Inn
Today’s route begins with a ride on the pathway that parallels the Trace through Jackson. On the edge of town, the Trace parallels the scenic Ross Barnett Reservoir. Then at milepost 122, there’s a cypress swamp nature area. This forms a transition from the river lowlands along the southern part of the Trace and the drier vegetation and landscape changes you see farther north. Walk the boardwalk for a peek into the lives of the swamp’s residents — maybe even a dozing alligator. A picnic lunch is included. At the end of the ride, we shuttle you back to Jackson, where you have a final celebration dinner at the Fairview Inn. (On the April 19-24, 2020, tour departure, we instead stay at the Old Capitol Inn in Ridgeland and dine together at a local restaurant.)
DAY 6 - Departure Day
Distance: 0 or 20 miles | Terrain: Easier
Your final morning features a visit to the Museum of Mississippi History and the Mississippi Civil Rights Museum — two new interconnected museums that take you through the sweep of Mississippi history and the state’s role as ground zero in the U.S. Civil Rights Movement. These help put your visit to Mississippi into a more recent historical context. If you prefer to ride, your last day of cycling features an out-and-back ride south on the Trace from the Clinton Visitor Center, where you’ll have one more chance to enjoy the quiet and scenic beauty of riding on the Parkway. Riders and museum goers may have lunch at their leisure, and we offer a shuttle to lunch options nearby.

Itinerary

From start to finish, check out the route.

DAY 1 - Arrival Day
Arrival Day | Distance: 20 or 40 miles | Terrain: Easier | The Monmouth Historic Inn and Gardens
Meet your leaders at the Home 2 Suites in Ridgeland, Mississippi, at 9 a.m. on Sunday, and head out on the Natchez Trace Parkway for your first ride. As you pass through Clinton, stop by the visitor center museum highlighting the history of the Trace and of Clinton. As you continue south, you see the historic location of the Battle of Raymond, where General Ulysses S. Grant’s troops clashed with the confederate brigade of General John Gregg on May 8, 1863. Pedal through history at Dean’s Stand where General Grant made his headquarters after the Battle of Raymond. And see Red Bluff Stand, which previously served as the boundary between the Choctaw tribe and three different nations: France, Spain, and the U.S. A picnic lunch is included. Finish the day with a walk to Rocky Springs, an abandoned town from the late 1800s. Then shuttle to Natchez for your first night in Mississippi’s oldest town — with dinner at our historic hotel, the Monmouth Inn. This exquisite inn was built in 1818 and is listed as a National Historic Landmark.
DAY 2 - Natchez Trace Parkway Ride
Distance: 30 or 50 Miles | Terrain: Easier | The Monmouth Historic Inn and Gardens
Today you explore Natchez and the surrounding countryside. After taking time to tour Monmouth Inn, you cycle to sites preserved by the National Park Service and others — including the Melrose Estate, which was one of the first plantation-style estates built inside a southern city. You also ride through Natchez and the historic riverfront area, where you may choose to stop for lunch. Lunch is on your own with suggested options. If you’re looking for longer miles, you can also do an out-and-back ride on the southern end of the Trace. This is the Deep South! Spanish moss hangs from the trees, and the scenery varies from hardwood forest to open pastures and cotton fields. Dinner tonight is on your own, with a wide variety of restaurants to choose from in Natchez.
DAY 3 - Emerald Mound & Windsor Ruins
Distance: 20 or 50 miles | Terrain: Easier | Canemount Plantation Inn
Head north this morning on the Natchez Trace and then onto rural side roads. Explore some of the historical artifacts along the Trace, including Emerald Mound — the second largest Indian mound site in the U.S. Ride past Alcorn State University, founded in 1871 by the Reconstruction-era legislature to provide higher education to freedmen. A picnic lunch is included. Along the route, visit the Windsor Ruins — built in the mid-1850s — a plantation that once sprawled over 2,600 acres, which now appears like a Roman ruin, thanks to the 23 still-standing columns. Your home for the night is the Canemount Plantation Inn, a historic 1850s house and grounds that have recently been converted into a B&B. Dinner is at the inn.
DAY 4 - Sunken Trace
Distance: 25 or 40 miles | Terrain: Easier | Old Capitol Inn
The riding today brings you farther north along the Natchez Trace back toward Jackson. See the charming town of Port Gibson and enjoy the quiet scenery on the way back to Rocky Springs. You also visit the Sunken Trace, a preserved section of the original route, where you can easily imagine a lone horseman appearing around the bend on his arduous wilderness journey. A picnic lunch is included. End the day at the edge of Jackson, with a short shuttle to the most elegant Inn in town. Relax and enjoy the privacy of this small, stately inn or explore town in late afternoon and visit sites such as the Eudora Welty Museum. Dinner tonight is on your own in Jackson, with many choices available. (On the April 19-24, 2020, tour departure, we instead stay at the Old Capitol Inn in Ridgeland.)
DAY 5 - Scenic Ross Barnett Reservoir
Distance: 30 to 60 miles | Terrain: Easier | Old Capitol Inn
Today’s route begins with a ride on the pathway that parallels the Trace through Jackson. On the edge of town, the Trace parallels the scenic Ross Barnett Reservoir. Then at milepost 122, there’s a cypress swamp nature area. This forms a transition from the river lowlands along the southern part of the Trace and the drier vegetation and landscape changes you see farther north. Walk the boardwalk for a peek into the lives of the swamp’s residents — maybe even a dozing alligator. A picnic lunch is included. At the end of the ride, we shuttle you back to Jackson, where you have a final celebration dinner at the Fairview Inn. (On the April 19-24, 2020, tour departure, we instead stay at the Old Capitol Inn in Ridgeland and dine together at a local restaurant.)
DAY 6 - Departure Day
Distance: 0 or 20 miles | Terrain: Easier
Your final morning features a visit to the Museum of Mississippi History and the Mississippi Civil Rights Museum — two new interconnected museums that take you through the sweep of Mississippi history and the state’s role as ground zero in the U.S. Civil Rights Movement. These help put your visit to Mississippi into a more recent historical context. If you prefer to ride, your last day of cycling features an out-and-back ride south on the Trace from the Clinton Visitor Center, where you’ll have one more chance to enjoy the quiet and scenic beauty of riding on the Parkway. Riders and museum goers may have lunch at their leisure, and we offer a shuttle to lunch options nearby.

Map

Map of Natchez Trace

Dates & Pricing

Make your reservation with confidence. Your tour is completely 100% refundable until the final payment due date.

Start End Cost Availability
Apr 19, 2020 Apr 24, 2020 $2295.00 Available! Reserve Reserve
Apr 26, 2020 May 01, 2020 $2295.00 Available! Reserve Reserve
Oct 18, 2020 Oct 23, 2020 $2295.00 Available! Reserve Reserve
Oct 25, 2020 Oct 30, 2020 $2295.00 Available! Reserve Reserve

What’s Included

Entrance fee to the Museum of Mississippi History and the Mississippi Civil Rights Museum, 5 nights’ lodging, 5 breakfasts, 4 lunches (you are on your own for 1 lunch in Natchez), 3 dinners (you are on your own for 1 dinner in Natchez and Jackson), all gratuities for accommodations and included meals, detailed maps and itineraries, experienced guides, full van support — plus use of a bike and helmet. Airfare is not included.

Dates & Pricing

Make your reservation with confidence. Your tour is completely 100% refundable until the final payment due date.

Start: Apr 19, 2020
End: Apr 24, 2020
Cost: $2295.00
Availability: Available!
Reserve
Start: Apr 26, 2020
End: May 01, 2020
Cost: $2295.00
Availability: Available!
Reserve
Start: Oct 18, 2020
End: Oct 23, 2020
Cost: $2295.00
Availability: Available!
Reserve
Start: Oct 25, 2020
End: Oct 30, 2020
Cost: $2295.00
Availability: Available!
Reserve

What’s Included

Entrance fee to the Museum of Mississippi History and the Mississippi Civil Rights Museum, 5 nights’ lodging, 5 breakfasts, 4 lunches (you are on your own for 1 lunch in Natchez), 3 dinners (you are on your own for 1 dinner in Natchez and Jackson), all gratuities for accommodations and included meals, detailed maps and itineraries, experienced guides, full van support — plus use of a bike and helmet. Airfare is not included.

Inns

Where you stay along the way.

The Monmouth Historic Inn and Gardens
The Monmouth Historic Inn and Gardens showcases all that’s charming about the south. With gracious hospitality, fine southern cuisine, and elegant rooms here, you’ll enjoy your stay.
Canemount Plantation Inn
The Canemount Plantation Inn is situated on a historic property with the main house constructed in 1855. Enjoy the wraparound gallery porch and the bubbling fountain. Stay in one of the beautiful suites in the carriage house, built in 1829, and enjoy this secluded 40-acre property surrounded by a 3,500-acre wildlife area.
Fairview Inn
Built in 1908, this fully renovated Colonial Revival mansion treats you to modern amenities in a historic location. It features gardens, decks, rocking chairs on the veranda … and even a gazebo to unwind from biking.

Inns

Where you stay along the way.

The Monmouth Historic Inn and Gardens
The Monmouth Historic Inn and Gardens showcases all that’s charming about the south. With gracious hospitality, fine southern cuisine, and elegant rooms here, you’ll enjoy your stay.
Canemount Plantation Inn
The Canemount Plantation Inn is situated on a historic property with the main house constructed in 1855. Enjoy the wraparound gallery porch and the bubbling fountain. Stay in one of the beautiful suites in the carriage house, built in 1829, and enjoy this secluded 40-acre property surrounded by a 3,500-acre wildlife area.
Old Capitol Inn

Gallery

Images from this tour. Click each to see it larger.

Natchez Trace Natchez Trace ruin site Armadillo Natchez Trace Fairview Inn guest pantry Fairview Inn with van Natchez Trace Fall