Antebellum mansions, southern hospitality, and miles of open roads – Welcome to Mississippi! Tour antiquated mansions that date back to the Civil War, discover the deep roots of this region on visits to monuments and historic sites and savor some of the south’s most delectable cuisine. Cycle along the peaceful Natchez Trace Parkway, a cyclist’s paradise that is a well-paved limited access highway with very little traffic, no cross traffic or traffic lights, and no commercial traffic. Spin down the Mississippi River Trail, a designated bicycle route network that parallels the length of the Mississippi River on this Natchez Trace cycling trip.
This unique adventure begins and ends in Jackson, the state capital of Mississippi. The ride is centered around the Natchez Trace Parkway, a 440-mile route steeped in history that is now part of the National Park System, with many historic sites along the route to pause and catch your breath. We’ll also enjoy trips off the Trace to nearby Vicksburg, one of the most historic and pivotal locations of the Civil War, and stopovers adjacent to the Trace in Natchez and Jackson. Enjoy true “southern hospitality” from the people of Mississippi on this Natchez Trace bike tour!
Welcome to Mississippi! Meet your leaders and take a two-hour shuttle ride to Natchez where we’ll begin our adventure. Enjoy a Sunday brunch and a tour of the famous Stanton Hall Historic Home. Take a warm-up ride around the town of Natchez that passes many of Natchez’s classic antebellum mansions. Tonight, our group will gather for a welcome reception and dinner at the Pilot House.
Follow a gently graded and scenic and winding route north on the Trace for 10 miles. Leaving the Trace takes us to Emerald Mound, the second-largest ceremonial mound in the nation built by the Natchez Indians. Enjoy lunch at the beautifully restored Cedars Plantation for lunch in the rural town of Church Hill. After lunch the route will rejoin the Trace heading back south towards Natchez, passing through Mt. Locust. Loop back to the southern terminus of the Trace and head back to the Guesthouse Manor.
Ride north to Windsor Ruins, a historic site featuring the remains of an antebellum mansion. Head to Port Gibson the 3rd oldest settlement in Mississippi. Many of Port Gibson’s historic buildings survived the Civil War because Grant believed the city was “too beautiful to burn.” Stop at the “Sunken Trace”, before settling in for a picnic lunch at Rocky Springs. The route then continues up the Trace to a picnic lunch hosted by your leaders at the ruins of Rocky Springs. Take the bicycle designated Mississippi River Trail (MRT) to Vicksburg, our home for the next two nights, before enjoying a group dinner at a local restaurant.
After breakfast, the owner of the Corners Mansion will give a tour of her property, and then we’re off to enjoy a guided tour of the historic Vicksburg National Military Park provided by a local historian. Embark on the route through the park and then we’ll arrive at the USS Cairo (a recovered sunken ironclad boat) Museum where your leaders will host a picnic lunch. After lunch, continue riding or head back to the Corners Mansion. This evening your leaders will host a wine and beer reception at the Corners Mansion and then you are free to explore Vicksburg on your own
Leaving the hills of Vicksburg behind us, our ride goes from urban to suburban to very rural farmland. Rejoin the Trace Parkway one last time for 10 miles and exit at the historic town of Clinton, a suburb of Jackson. Lunch will be at the 303 Jefferson restaurant in the center of the historic red-bricked downtown. For our final encore, we’ll ride down Capitol Street through the heart of downtown Jackson, past the Governor’s Mansion and Old Capitol building before arriving at the Old Capitol Inn. After freshening up, join your fellow travelers for a drink on the hotel's rooftop lounge before we head out for a final farewell hosted group dinner.
The morning if free and open for you to explore/ Breakfast will be available starting at 7 AM and we will leave for the airport after checkout at noon.
This historic mansion was originally built in 1840 by the grandson of Natchez’s first mayor and prides itself on its deep rooted history and antebellum architecture, featuring an elegant interior, a French Quarter Style Courtyard, and expansive porches. (2 Nights)Lodging Website
This boutique hotel dates back to 1952 and is within walking distance of the Mississippi State Capitol building and the Old Capitol Museum, from which it takes its name. The inn features a rooftop garden with stunning views of the city and evening wine-and-cheese receptions. (1 Night)Lodging Website
Located in Vicksburg’s Historic Garden District, The Corners is a true Southern Mansion with original parterre gardens and views of the Mississippi River. The Mansion enjoys stunning sunset views from the galleries features porch swings on the front porch. (2 Nights)Lodging Website
Reserve one of our regularly scheduled trip dates for your private group and qualify for reduced pricing. The larger your group, the lower the per person price. Gather your friends and we’ll do the rest to provide your group with a truly personalized and memorable vacation. Smaller groups can join published trips and receive reduced pricing on trips that aren’t reserved as private trip dates.
For groups of 16-18 people traveling together on a published tour date, a 10% discount on the double occupancy trip price will apply.
For groups of 12-15 people traveling together on a published tour date, a discount of 8% on the double occupancy trip price will apply.
For groups of 8-11 people traveling together on a published date, a discount of 6% on the double occupancy trip price will apply.
Group discounts may not be combined with other offers.