Following The Cherokee Trail of Tears

Following The Cherokee Trail of Tears

Missionary Daniel Butrick kept a journal of his travels with the Cherokee People as they were force marched to Indian Territory during the winter of 1838-39. It is one of the saddest episodes in American history, with the depths of despair grippingly described by him in this entry:

“… the government might more mercifully have put to death everyone under a year or over sixty; rather it had chosen a more expensive and painful way of exterminating these poor people.”

Breaking Away from the Beltway

In pre-Columbian times, the Cherokee People’s land stretched from the Ohio River to present-day Kentucky, Tennessee, North Carolina, South Carolina, Georgia, and Alabama. But by the early 1800s, various treaties had reduced Cherokee land to a fraction of their former size. At the same time, European diseases devastated much of the Cherokee Nation. Those who survived adopted many aspects of European culture and enterprise, including farming, a written language, a court system, a printed newspaper, and even Christianity. Cherokee settlements looked and functioned much the same as white settlements of the day. However, in 1828, gold was discovered on Cherokee land in North Georgia, and white settlers began ignoring legal Cherokee boundaries. By 1830, the Cherokee had lost any legal claim to their lands. That year, Congress passed the Indian Removal Act, and President Andrew Jackson signed it into law; he had long advocated Indian removal to lands west of the Mississippi River.

Bob Brown and I start our journey at the US Capitol in Washington, DC, on a hot, humid day in early September. After touring the National Museum of the American Indian, it’s time to motor south and explore the Cherokee Trail of Tears. Bob (my intrepid travel companion on this long-distance adventure) and I spend the next three days enjoying the stunning scenery of the Blue Ridge Parkway on our way to Cherokee, NC.


With official Trail of Tears road signage in front, the Chattanooga Choo Choo is literally right on the trail and within walking distance of inviting downtown eateries. This former train station is one of those iconic lodgings that shouldn’t be missed, especially the opportunity to stay in one of the vintage train cars. Find it at 1400 Market St, Chattanooga, TN, (800) 872-2529


Insufficiently Celebrated Genius

Cherokee, NC, is the present-day home base for the Eastern Band of Cherokee Indians, descendants of some 800 who remained after the other 15,000 members of the tribe were forced to resettle in Indian Territory (present-day Oklahoma). Today, Cherokee, NC is a small but vibrant resort town. Gaming establishments are available for adults, and a host of outdoor activities and shopping venues abound. But Bob and I are focused on learning more about the Cherokee People themselves. There’s no better place to start than the Museum of the Cherokee Indian in downtown Cherokee. We spend several hours perusing numerous artifacts, exhibits, sculptures, dioramas, and other artwork recounting Cherokee culture and seminal events in Cherokee history. It’s easy to see why some referred to them as one of the “Five Civilized Tribes,” virtually all of which were removed from the southeastern states. By late morning we’re back on the pavement following some of the region’s most iconic roads. My goal in designing this route was to enjoy interesting roads between the various Trail of Tears historical sites. First up is the Tail of the Dragon. Although it’s a relatively short distance, the 318 curves make it seem much longer—it can be an exhausting experience to navigate.


Motorcycles & Gear

The riders in this story used the following motorcycles and gear, which worked perfectly for this tour.

Shop this look with the links below.

2016 Indian Roadmaster
2016 Indian Chief Vintage

Helmets: Schuberth 3C Pro Modular, Shoei GT-Air
Jackets: Indian Motorcycle Tour, Speed and Strength Society Leather
Pants: Draggin Jeans, Draggin Jeans Retro Fit
Boots: Oxtar, BMW Airflow 3
Gloves: Klim Element Short, REV’IT! Sand Pro


Continuing farther west, to an island in Tennessee’s Tellico Lake , we find reconstructed Fort Loudon. The British colony of South Carolina built the original fort here during the French and Indian War (1754-1763). This helped to ally the Overhill Cherokee Nation in the fight with the French and preserve trade with the Cherokee. But relations broke down in the 19th century, and the Cherokee captured Fort Loudon in August 1860.