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The detachment led by Elijah Hicks took about nine days to cross southern Illinois while the last ten detachments became bogged down for many reasons and consequently took much longer, mainly due to the early arrival of a severe and deadly winter.
In fact, conditions were so horrendous this segment of the Trail records the highest mortality rate of any state the Cherokee passed through, thus making the Trail of Tears route through Illinois one of the most tragic stories of Native American removal.
Historian Charles Logan suggests that because the Cherokees conducted themselves, the details concerning the total number of emigrants, the number of deaths and their suffering are more difficult to ascertain than with previous parties led by military conductors, who kept detailed daily logs.
From here the 11 detachments crossing Southern Illinois chose various routes. Some detachments traveled south along what is now Route 146 and camped just southeast of Vienna. Most groups continued west along the Golconda - Cape Girardeau route, but some of the earlier detachments continued southwest of Vienna along an old road to Belknap.
Near Belknap they turned west and camped just south of Cypress Creek before traveling the Belknap-Cypress-Dongola Road into Dongola. From Dongola they traveled the St. John's Road north to Kornthal Church Road following the Old Cape Road west through what is now Reynoldsville, then north along Levee Road to Hamburg Landing.
Another group traveled further north up through the Tunnel Hill area and then over towards Goreville where they took shelter at Ferne Clyffe.
The remaining detachments continued along the Golconda - Cape Girardeau route traveling west of Vienna, following what is now Route 146. Entering Union County, the Cherokee passed through Pleasant Grove and Mt. Pleasant to the site of the present-day Camp Ground Church. This was a common campground for travelers and it is likely that many of the detachments stopped and camped here and perhaps buried their dead near an existing small family cemetery.
These groups followed Camp Ground Road to Old Saratoga Road which led to a campsite about 5 km west of Jonesboro and eventually to Hamburg Landing where they crossed the Mississippi River to Bainbridge, Missouri using Smith's Ferry.
Most detachments traveled slightly north of the Old Hamburg Road to camp along Dutch Creek on the Morgan Farm and later proceeded to Willard's Landing where they crossed the Mississippi River to Moccasin Springs, Missouri. While many detachments crossed at Willard’s Landing, at least two crossed at New Hamburg to Bainbridge. The horse-drawn ferry boats at the landings could only carry a few people at a time; therefore it took several days for a detachment to cross the river, even if the weather cooperated.
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