Rating Level: Easy/ModerateStately Greek revival mansions, historic Civil War battlegrounds and gracious hospitality await you on this delightful excursion into the antebellum South.
Set your own pace for discovery on this flexible itinerary, as we follow the commercial traffic-free Natchez Trace Parkway from the eerie ghost town of Rocky Springs to the thriving community of Natchez, where the opulent pre-Civil War era is proudly preserved. Along the way, we’ll marvel at scenic vistas and probe our nation’s past in the company of a local expert. And we’ll experience contemporary Southern pride firsthand at the accommodations we have selected—including two inns that have earned national recognition.
ADMIRE scenic vistas and historic monuments along the Natchez Trace Parkway
FIND history brought to life by a local historian at Vicksburg National Military Park
RECALL the antebellum South during a “Pilgrimage” of Natchez's mansions
WHISK into Natchez for dinner by horse-and-carriage
VISIT Emerald Mound, one of the largest Native American ceremonial mounds on the continent
SAVOR delicious Southern cuisine—including hearty breakfasts and a 5-course candlelight dinner
STAY at Monmouth Plantation, one of the nation's most highly acclaimed inns
DELIGHT in Mississippi's idyllic climate during the spring and fall
This tour offers a combination of primarily easy terrain mixed with some rolling hills (Day 3 inside Vicksburg National Military Park being the most notable). Our VBT van support shuttle is always available for those who need assistance. This trip is ideal for both beginning and experienced cyclists.
Rating Level: Easy/Moderate
Daily Mileage: 15-49 miles
Daily Cycling Time: 2-5 hours
Welcome to Mississippi! Make your own arrangements for travel to the Fairview Inn, where we stay for one night and get our first sampling of Southern hospitality. If you're flying in, you might meet VBT's complimentary shuttle upon your arrival at Jackson-Evers International Airport. The shuttle works on a “show and go” basis and will make its only departure from the airport to the inn at 2 p.m. Shuttle reservations are not required and not available. Meet the driver and bus in the third lane as you exit the airport in the baggage claim area. The bus will say Cline Tours and will have a VBT Bicycling and Walking Vacations sign. If you are scheduled to arrive at the airport after 2 p.m. 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 p.m., 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. It was the home of the internationally acclaimed author from 1925 until her death in 2001 and the site where she wrote almost all of her fiction and essays. At 5:30 p.m., get to know your fellow travelers during a welcome reception and tour orientation. Southern hospitality continues with dinner at our inn. The much-heralded Fairview Inn is Jackson's only AAA Four Diamond-rated accommodation. Guests wishing to enjoy the spa are encouraged to make reservations in advance.
This morning, after our first Southern breakfast, we'll shuttle (approximately 60 minutes) to Dean's Stand on the Natchez Trace Parkway. Here, we start our ride to the curious and eerie town of Rocky Springs and continue 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 were the final straws that 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. 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 both 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 fire due to 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 and our lodging for two nights. Upon arrival at The Corners, our innkeepers introduce us to this charming 1873 house. The inn features a unique blend of architectural styles, and its pierced columns and parterre gardens have earned it an appointment to the National Register of Historic Places. Enjoy the gardens, porch and verandah, the double parlor and your charming room. The inn rests high on a bluff, and from its 68-foot-long porch, you'll have lovely views of the Mississippi and Yazoo rivers. Hosts Macy and Joe will make you feel right at home. Tonight, we will enjoy dinner on the glassed-in verandah at our inn.
Wake up to another hearty Southern breakfast. You'll want to allow plenty of time to enjoy it! Riding out from the inn, 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. Historian Harold Lee 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. Before leaving the park, be sure to visit the USS Cairo Museum and the reassembled ironclad Union gunboat that was sunk by a mine. This is where we enjoy a picnic lunch and learn more about the decisive Siege of Vicksburg.
Cycling back to the inn, stop for a worthwhile visit at 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 a story, some of which you'll find quite unusual.
Tonight, enjoy dinner on your own in the town of Vicksburg.
After breakfast, we'll shuttle to Port Gibson, where we'll join the Natchez Trace Parkway again and head 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 the hardwood pine forests around Bullen Creek. Enjoy a picnic lunch prepared by your leaders at Coles Creek, and then pause at Mount Locust, Mississippi's first inn that served 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 for the local villagers 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 some 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 to Monmouth Plantation, a National Historic Landmark that has received the highest praise from the likes of Condé Nast Traveler and Travel + Leisure magazines. We'll stay here for the next two nights, perhaps indulging in a game of croquet and strolls through its expansive gardens. Upon arrival here, retreat to the study for your favorite drink and a lively start to the evening.
Tonight, horse-drawn carriages carry us through town, where you'll find a number of excellent options for dinner on your own.
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 or worse, 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.
Pilgrimage grew into a multi-week event in the spring, and even dates in the fall were added. But in reality, many of these homes offer guided visits year round. It's 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 the town has to offer. We've included admission for you to tour a number of the finest homes, riding and visiting at your own pace. Choose from guided visits of the ornate, octagonal (yet unfinished) Longwood; Rosalie, known for its rosewood furniture; Stanton Hall, owned by the Pilgrimage Garden Club; and others. 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 Plantation.
Tonight, enjoy a memorable five-course candlelight dinner of contemporary Southern cuisine in our inn's acclaimed dining room.
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 Natchez at 9:30 a.m., arriving at the airport around 12:00 noon, and at the inn at 12:30 pm. We suggest you schedule your flight home no earlier than 1:30 p.m.
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Mar 71° Apr 78° May 84° |
Sep 87° Oct 80° Nov 70° |
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March 22, 2012 |
$1,945 |
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April 5, 2012 |
$1,945 |
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April 12, 2012 |
$1,945 |
|
April 26, 2012 |
$1,845 |
|
May 10, 2012 |
$1,845 |
|
September 27, 2012 |
$1,945 |
|
October 4, 2012 |
$1,945 |
|
October 18, 2012 |
$1,945 |
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October 25, 2012 |
$1,945 |
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November 1, 2012 |
$1,945 |
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November 15, 2012 |
$1,845 |
Please note: Standard Terms & Conditions apply when purchasing this trip. Government taxes and fees are included in your airfare price. Fees billed by airlines are shown separately on your invoice. Ask our Tour Consultants for details. Every effort has been made to produce this information accurately. We reserve the right to correct errors. Prices are based on preferences selected above, including meals and sightseeing as specified in What's Included. All prices are subject to change. Departure dates and prices shown may be updated several times daily, and apply to new bookings only.
The Fairview Inn is Jackson’s only AAA four-diamond small luxury hotel. Offering unique lodging in a historic 1908 Colonial Revival mansion, this bed-and-breakfast inn is one of the few remaining architecturally designed homes of that period. You’ll find that it exudes the rich history of Jackson, Mississippi.
Listed on the National Register of Historic Places and conveniently located in the Belhaven historic neighborhood adjacent to Millsaps and Belhaven colleges, the Fairview Inn is minutes away from downtown Jackson's arts, theater, museums and shopping. Antique and boutique shops are in the nearby Fondren District.
Originally presented as a wedding gift, this lovely property was built in 1873. The Corners sits atop a bluff overlooking the Mississippi Valley and River. Relax and enjoy the views from rockers on the front Gallery. The large double parlor with its floor to ceiling windows and baby grand piano is an ideal place to enjoy an after-dinner drink with friends. Fifteen rooms offer a choice of southern elegance, Victorian charm or country simplicity. All rooms have private bath, color television and air conditioning.
Bask in Southern luxury at its finest. Built in 1818, the 26-acre Tara-like Monmouth Plantation features lovely gardens and pergolas, a gazebo, bridge-spanned ponds and walking trails. This magnificent manse was once owned by U.S. Congressman and State Governor John Quitman. His dream for Monmouth has been fully realized through the loving and careful restoration of the mansion and the addition of seven other buildings on this historic property. Today, Ron and Lani Riches make you feel at home amid the quiet elegance of 29 beautifully appointed rooms and suites. This National Historic Landmark has earned praise from the likes of Condé Nast Traveler, The New York Times and Architectural Digest. Take your breakfast in Quitman’s Retreat, meet for drinks in the Quitman Study, and savor “Chef’s Table Dining” during our special farewell dinner.
|
Mar 71° Apr 78° May 84° |
Sep 87° Oct 80° Nov 70° |
This tour offers a combination of primarily easy terrain mixed with some rolling hills (Day 3 inside Vicksburg National Military Park being the most notable). Our VBT van support shuttle is always available for those who need assistance. This trip is ideal for both beginning and experienced cyclists.
|
Mar 71° Apr 78° May 84° |
Sep 87° Oct 80° Nov 70° |

Occasionally, unforeseen circumstances may arise which may cause you to either cancel or interrupt your vacation. We are committed to providing the best value for your travel dollar. That is why we include an insurance program on your invoice.
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TRIP CANCELLATION |
TRIP COST |
|
TRIP INTERRUPTION |
150% of Trip Cost |
|
TRAVEL DELAY ($150 MAXIMUM PER DAY) |
$750 |
|
BAGGAGE & PERSONAL EFFECTS |
$1,500 |
|
BAGGAGE DELAY ($150 MAXIMUM PER DAY) |
$750 |
|
ACCIDENT AND SICKNESS MEDICAL EXPENSE |
$50,000 |
|
EMERGENCY MEDICAL EVACUATION |
$100,000 |
|
ACCIDENTAL DEATH & DISMEMBERMENT |
$25,000 |
|
ONE CALL 24HR ASSISTANCE SERVICES* |
INCLUDED |
|
ONE CALL TRAVEL SOLUTIONS* |
INCLUDED |
|
ONE CALL CONCIERGE SERVICES* |
INCLUDED |
*These are non-insurance services provided by One Call Worldwide Travel Services Network.
Insurance is underwritten by United States Fire Insurance Company, Eatontown, NJ. This is only a brief description of the plan. The Plan Certificate, which fully details the Benefits, Limitations, and Provisions of the plan is available at www.vbt.com. This plan is administered by Trip Mate, Inc. (in CA, Trip Mate Insurance Agency), 9225 Ward Parkway, Kansas City, MO 64114 800-888-7292.
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Tour Cost Per Person |
Plan Cost Per Person |
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$1,001-$1,500 |
$165 |
|
$1,501-$2,000 |
$220 |
|
$2,001-$2,500 |
$265 |
|
$2,501-$3,000 |
$320 |
|
$3,001-$3,500 |
$375 |
|
$3,501-$4,000 |
$415 |
|
$4,001-$4,500 |
$450 |
|
$4,501-$5,000 |
$490 |
|
$5,001-$6,000 |
$585 |
|
$6,000-$7,000 |
$625 |
Please Note: The rates shown are per-person and are subject to change, and include coverage for the air portion of your itinerary if VBT Active Vacations is arranging your air transportation. The Travel Protection Plan cannot be purchased after you have made your final payment or once you are inside the penalty period, whichever comes first. The cost of your Travel Protection Plan is non-refundable.
Pre-Existing Medical Condition Exclusion is waived if the plan is purchased within 14 days of initial trip payment.