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Biking Vacation Mississippi: The Natchez Trace​

Activity Level: Easy / Moderate  |  Daily Mileage: 15 – 49 mi  |  Daily Biking: 2 – 5 hr
Land only
6 days from only
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Detailed Itinerary 

Please note: For those traveling in 2015, your itinerary may vary slightly from what is presented below. 

Day 1 - Arrive Jackson / Warm-up ride / Welcome reception and dinner

Begin your Mississippi vacation! Make your own arrangements for travel to the Fairview Inn, where we stay for one night and get our first sample of Southern hospitality. If you're flying in, you'll have the option to meet VBT's complimentary shuttle upon your arrival at Jackson-Evers International Airport. Shuttle reservations are not required as the shuttle works on a “show and go” basis and will make its only departure from the airport to the inn at 2:00 pm. 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. They will also be holding a VBT sign. If you are scheduled to arrive at the airport after 2:00 pm or if you are delayed, you must take a taxi 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 first inn; they will inform your VBT Trip Leaders.

At 3:30 pm, meet your VBT Trip Leaders and the rest of the group at the inn for a safety and bike-fitting session, followed by a short warm-up ride. The ride, through a primarily residential neighborhood of Jackson, passes the Eudora Welty House, at 1119 Pinehurst. The world-famous author lived and worked here, composing almost all of her work in this very home from 1925 until she passed in 2001.

At 5:30 pm, get to know your fellow travelers during a welcome reception and tour orientation at the inn. Next, we'll venture out with our leaders for dinner at a nearby restaurant.

Guests wishing to enjoy the spa at the inn are encouraged to make reservations in advance.

Day 2 - Rocky Springs / Vicksburg

This morning, after our first Southern breakfast, we'll shuttle (approximately 60 minutes) to the curious, eerie town of Rocky Springs and then cycle on the parkway to Port Gibson.

The Old Natchez Trace was a 500-mile footpath that ran through the lands of Choctaw and Chickasaw tribes, and it connected Natchez, Mississippi, to Nashville, Tennessee. Today's pastoral parkway loosely follows the route of the old trace. It took 71 years to complete, is managed by the National Park Service and was designated an All-American Road by the U.S. Department of Transportation. That means no commercial traffic is permitted, and the speed is limited to 50 mph. 

Rocky Springs was, for many years during the latter part of the 18th and most of the 19th century, a thriving community on the Old Natchez Trace. In 1878, the town was struck by yellow fever, and in the early 1900s the boll weevil destroyed most of the cotton crop. Burdensome taxes, the town's inaccessibility and almost 100 years of poor farm management and soil erosion ultimately led to the town's demise. One by one, the citizens began to move away. Finally, in the 1930s, the last store closed, and even the natural springs for which the town was named began to dry up. One of its only surviving, intact buildings is the Methodist Church.

Continuing on, we will arrive in Port Gibson, the town declared “too beautiful to burn” by Ulysses S. Grant during his Siege of Vicksburg. Once in Port Gibson, explore the historic town, or continue on to visit Windsor Ruins. Windsor was built by Smith Coffee Daniel II just prior to the start of the Civil War. He died tragically at the age of 34, just a few weeks after the mansion was completed. Set on a plantation that originally covered 2,600 acres, the four-story home had 25 rooms, 25 fireplaces and a school and dairy at the basement level. Confederate troops used the roof observatory to watch for Union advances. Windsor survived the war, thanks to its use as a Union hospital. But irony lent a merciless hand in 1890, when this magnificent home was lost to a fire brought on by a careless smoker. Today, all that remains of Windsor are 23 of the original 29 columns, each 45 feet tall, plus a piece of the balustrade that connected them.

After lunch in Port Gibson, we will shuttle to Vicksburg, where we'll stay for two nights. Our accommodations are in two of the town's finest historic mansions – Baer House Inn and Anchuca Mansion – both located in Mississippi's Historic District, so you'll savor every moment no matter which you call home. After settling in, we'll gather together at Anchuca Mansion for dinner.

Day 3 - Vicksburg Battlefield loop

Wake up to another hearty Southern breakfast this morning. You'll want to allow plenty of time to enjoy it! Riding out from the inns, we cycle through Vicksburg and the overlooks of the Mississippi, through Civil War battlefields and into the Vicksburg National Military Park. We'll ride through the park, stopping at the Visitor Center, where you might choose to watch a short orientation film. A local historian will join us in the park to bring history alive, and we'll stop at select monuments for discussion. 

Today's ride is perhaps the week's most challenging; the park roads stretch over a series of rolling hills set above the Mississippi. Naturally, you'll want to tour “the battlefield loop” at a pace that suits you, stopping at the interpretive markers and monuments along the low-trafficked park roads. This is where we enjoy a picnic lunch and learn more about the decisive Siege of Vicksburg. Before leaving the park, be sure to visit the USS Cairo Museum and the reassembled ironclad Union gunboat that was sunk by a mine.

Cycling back to the inns, stop for a worthwhile visit to the Old Courthouse Museum, housed in one of the city's most impressive antebellum buildings. Its nine rooms are packed with artifacts donated by residents, and each is marked with an interesting or even unusual story.

Tonight, enjoy dinner on your own in the town of Vicksburg.

Day 4 - Natchez Trace Parkway / Emerald Mound

After breakfast, we'll shuttle to Port Gibson, where we'll rejoin the Natchez Trace Parkway, heading south to Natchez. Along the way, you'll have several opportunities to pause and take in some of the parkway's vistas and historic sites. You might take a break along the way to stroll through the hardwood pine forests around Bullen Creek. Enjoy a picnic lunch prepared by your leaders at Coles Creek, and then linger awhile at Mount Locust, Mississippi's first inn, serving warm meals and a cozy bed to weary travelers seeking a respite from their journey on the trace.

Next, pedal to Emerald Mound, built by ancestors of the Natchez Indians. Designated a National Historic Landmark, Emerald Mound is one of the largest mounds in North America, covering eight acres. The mound was built by depositing earth along the sides of a natural hill, thus reshaping it and creating an enormous artificial plateau. Emerald Mound was created and used as a ceremonial center by the local residents during the Mississippian period between 1250 and 1600. By the late 1600s, the Natchez had abandoned Emerald Mound and established their capital at the Grand Village, about 12 miles to the southwest.

Continuing on, perhaps you'll stop to visit the Elizabeth Female Academy, the state's first school for women. Then, ride into Natchez and on to Monmouth Historic Inn, a National Historic Landmark that has received the highest praise from the likes of Condé Nast Traveler and Travel + Leisure magazines. Upon arrival, retreat to the study for your favorite drink and a lively start to the evening. We'll stay here for the next two nights, perhaps indulging in a few games of croquet or a stroll through the accommodation's expansive gardens.

Tonight, horse-drawn carriages carry us through town, where you'll find a number of excellent options for dinner on your own.

Day 5 - Antebellum Pilgrimage / Natchez

Natchez is known around the world for its Spring Pilgrimage, held every year between the first week of March and the first week in April. “Pilgrimage,” as it is now called, was started in the first half of the 20th century by Katherine Grafton Miller. Known as “Play Mama” to her friends, Miller convinced her fellow Garden Club members to open their homes to visitors for several days so all could see “where the Old South still lives and where shadowed highways and antebellum homes greet old and new friends.” These pilgrims, many from the north, were personally driven from home to home and regaled with tales told by ladies wearing hoop skirts and holding parasols. The money brought in by these efforts allowed the homes to escape disrepair, particularly during the days of the Great Depression. A well-publicized visit by First Lady Eleanor Roosevelt put the tradition on the map, and it continues today.

Eventually, Pilgrimage grew into a multi-week event, occurring in the spring, and in the fall. However, many of these homes offer guided visits year round and these visits have become Natchez' number-one draw, an ongoing and vital venture that keeps the city thriving.

Today, we reenact the pilgrimage, VBT-style, cycling a scenic route through Natchez, past magnolia and dogwood trees and taking in the best of the town. We've included admission for you to tour a number of the finest properties. Choose from guided tours of homes including Rosalie, known for its rosewood furniture, Stanton Hall, owned by the Pilgrimage Garden club and the ornate (yet unfinished), Longwood. And, of course, you'll ride to these historic homes at your own pace. Should you feel parched, you may wish to stop and enjoy a mint julep over lunch at the Carriage House Restaurant on Stanton Hall's grounds. The Carriage House is the local's choice for fried chicken, buttered biscuits and pecan pie.

For those seeking more mileage, pedal out to the Natchez Trace Parkway and cycle as far as you would like before retracing your way to Monmouth Historic Inn.

On the last night of your trip in Mississippi enjoy a memorable five-course, candlelight dinner of contemporary Southern cuisine in our inn's acclaimed dining room.

Day 6 - Depart for home

The tour concludes after breakfast. Join our complimentary shuttle to either Jackson-Evers International Airport or to our first inn in Jackson. The shuttle departs from Natchez at 9:00 am, arriving at the airport around 11:30 am, and at the inn at 12:00 pm. We suggest you schedule your flight home no earlier than 1:00 pm.

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