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cycling trip Natchez Trace National Parkway Cycling Tourleaf

Dates: 10/14 - 22, 2017

(9 days, 8 nights, Sat. - Sun.)


Assembly Point: Nashville, TN

(Timberline van shuttle is included from Nashville International Airport prior to tour and from Natchez to Jackson, MS following tour) *Note different airports

Not included Airline service to Nashville, TN and from Jackson, MS; Guide Gratuity

Meeting time: airport 1 pm, hotel 1:30 pm

Drop off time: 5 pm

Tour Cost: $3,298

Includes all lodging, all breakfasts, dinners, snacks, leaders, support van, park entrance fees, airport transfers, tour maps and narratives.

Additional Single Occupancy Lodging Cost: $599

Inn Highlights

  • Corners Mansion
  • French Camp B&B

From animal path to Indian trail to wilderness road, the Natchez Trace once traversed hundreds of miles of unbroken virgin forests.  Today, the Trace is known as the Natchez Trace Parkway National Park, 442 miles of paved roadway extending from its northern terminus just south of Nashville, TN, to Natchez, MS.  The parkway represents the culmination of decades of dedication and determination to preserve the history and heritage of this region. In so many ways, the Trace is an account of thousands of years of human habitation in the South, from the early Native American tribes to the settlers who breached the Appalachian barrier in their westward quest for new lands.  It is also the Antebellum South and a chronicle of the Civil War.

Most importantly for our purposes is the nature of the parkway itself.  Seventy years in its planning and construction, the parkway was never intended as a major avenue of commerce connecting major population centers of the South. Instead, its purpose was to offer travelers an opportunity to experience the history and heritage of the region.  The parkway is rural in character as it winds through miles of forested ridges and broad river valleys. There is no commercial traffic permitted on the parkway, so guests will not be competing with logging trucks, 18-wheelers, billboards, and strip malls. One must leave the parkway to access lodging, restaurants and stores. Without a doubt, the parkway is a cyclist’s fantasy, and it is one of America’s premier cycling experiences.    

In true Timberline style, we will cycle the full 442-mile parkway. We’ll assemble just south of Nashville and begin our journey on Day 1 along the Trace near Milepost 442 at the northern terminus.

Day 2, unquestionably one of the more challenging days, promises more than 2,000 feet of cumulative climbing along with ample rolling ridge-top terrain and some spectacular scenic vistas from those ridge tops.  We’ll spend our first overnight in Columbia and rejoin the Trace the following morning. Early into our ride on Day 3, we’ll visit the Meriwether Lewis Memorial, marking the grave of one of the leaders of the Lewis and Clark Expedition of 1804-1806.  We’ll cross into Alabama later in the day and spend the evening in Florence. We’re headed to Tupelo on Day 4, headquarters for the parkway and a town that needs to be explored.  The Battle of Tupelo was one of the major battles of the Civil War and we’ll visit the battlefield. However, Tupelo is perhaps best known as the birthplace of Elvis - the King.

Back on the parkway on Day 5 as we ride through the region that was home to the Chickasaw Nation before being driven from their homes by the U.S. Army.  We’ll also ride past Bynum Mounds ancient Native American burial grounds, and ultimately tonight we stay in the rustic cabins at the French Camp B&B where our host will prepare a true Southern meal for us this evening.  We’ll ride through the heart of central Mississippi on Day 6, through the Choctaw Indian Agency and the beautiful tupelo-cypress swamp south of the agency. We’re headed to Ridgeland on this day and we’ll spend the evening in this town that was the original Choctaw Indian Agency.

We’ll leave the parkway on Day 7 to visit historic Vicksburg, so rich in antebellum and civil war history. We’ll arrive early enough to tour this remarkable town situated on the Mississippi River. Along the way, we’ll ride past numerous grand antebellum homes that appear to have been transported from Gone With The Wind.  We’ll also visit the Vicksburg National Military Park and Battlefield and spend the evening at the grand Corners Mansion Inn. We’ll ride back to the parkway the following day as we ride to Port Gibson. General Ulysses Grant, upon visiting Port Gibson during his march through the South, commented that the town was “too beautiful to burn.”
We’ll ride to Natchez on our final day, arriving early afternoon with time to explore another town richly steeped in antebellum history. We’ll ultimately van shuttle to the Jackson airport, where our program concludes.


Pre-tour Arrive, assemble, bike fitting, orientation dinner  
Day 1 Natchez Trace Parkway — Northern Terminus — Backbone Ridge — Tennessee Valley Divide — Columbia 55 miles
Day 2 Columbia— Meriwether Lewis Historic Site — Laurel Hill Lake — Collinwood — Sunken Trace — Florence, AL. 59 miles
Day 3 Florence — Tennessee River — Tenn/Mississippi State Line — Tishimingo State Park — Natchez Trace Hdqtrs — Tupelo, MS 62 miles
Day 4 Tupelo — Chickasaw Village — Mathiston — Jeff Busby — French Camp 83 miles
Day 5 French Camp — Choctaw Agency — Ridgeland 69 miles
Day 6 Ridgeway — Vicksburg — Tour Vicksburg and Vicksburg National Battlefield 36 miles
Day 7 Vicksburg — Port Gibson. 54 miles
Day 8 Port Gibson — Springfield Plantation — Emerald Mound — Natchez 37 miles

Total cycling mileage: 472

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Routes, mileage and accommodations are subject to change due to safety, road/trail conditions, weather and availability.