In 1835, Featherstonhaugh travelled from Green Bay, Wisconsin, up the Fox River to the Wisconsin River, then downstream to Prairie du Chien, and into the Mississippi River. He paddled up the Mississippi, passing the St. Croix River and the Minnesota River, stopping at Carver's Cave and Saint Anthony Falls.^[9]

In August 1837 after travelling along the Mississippi, Ohio, and Tennessee rivers, Featherstonhaugh joined with Special Government Agent John Mason, Jr. to attend the Cherokee National Council at Red Clay, Tennessee, at the beginning of the crisis that eventually led to the Cherokee Removal, sometimes called the "Trail of Tears". He spent more than a month with these Indians, and was an eyewitness to the resistance of Principal Chief John Ross and the Cherokee people to the fraudulent Treaty of New Echota. The public purpose of his visit was to inspect for the federal government the geology of the mountainous regions of Georgia and North Carolina where gold had been discovered, but there was also another covert mission. In his memoirs, Featherstonhaugh described a pleasant encounter with a learned Welsh-born Baptist missionary Rev. Evan Jones, a fellow Britisher residing among the Cherokees. However, in a secret memoranda sent to General Winfield Scott in May 1838, he wrote: "Evan Jones, An Englishman of dark, cunning character. This man many years ago settled as a missionary amongst the Cherokee, knows their language well, and has had a great deal of personal intercourse with them. In the event of a rupture with these people, he is a person likely to give them bad advice, and I should advise his removal from the Nation." This memorandum also lists four other White men living with the Cherokees, analyses tribal politics, and provides an estimate of a possible military confrontation with the tribe because of the upland topography.