This was taken from History of Stoddard County, by Robert N. Forister

      Before the last glacial Ice Age, thousands of years ago, mammoths, camels, primitive horses and other now extinct animals roamed this area.  In History of Missouri, by Louis Houch, 1908, he located 3,211 mounds in Stoddard County, most of them aggregated around the town of Advance.  Archeological finds indicate a people called Mound Dwellers  had a very advanced culture.  They made excellent and artistic pottery , garments, stone implements and religious articles.  They constructed harbors for their huge dugouts, practiced extensive agriculture and practiced a complicated religion.  Articles of copper and silver have been found at the sites.  Their works resemble a striking resemblance to those in Central America. 

     When DeSoto and other explorers reached this area in the 1500's the mound dwellers culture had disappeared.  It is estimated that their towns contained more people than live in this area today.  Theirs  was the most advanced Indian cultures north of Mexico.  Archaeologist have found evidence that may link them with ancient civilizations on Asia Minor.   It appears that they migrated with their culture to this area, why they disappeared is a mystery.    One theory is their culture disappeared because to the buffalo extending their range to this area.  They may have been unable to exist on agriculture when the buffalo roamed free on their unfenced fields.  The mound dwellers were gone by the time white men appeared in this region.

     DeSoto was the first recorded white man to reach Southeast Missouri, in the 1540's.  Some theorize that the most obvious route would have been to follow the high and dry Shawnee Indian Trail.  which is approximately highway 25 along Crowley's Ridge.  The trail was used from ancient time, including the mound dwellers.

      DeSoto met Kaskaskia and Capaha Indians in the area  Early explorers reported that the Ozark plateaus or Flatwoods, were grassy prairies.  The timber must have grown after the white man arrived.

     The vast swamps of Stoddard County were covered with giant virgin cypress and other trees except for a few open prairie islands.  The swamps were so thick with moss only with dugouts or on ice in winter could anyone travel the swamps .   Even then he could become lost.  Many swamps were unchanged until the drainage program in the 1800's and early 20th Century.  Around 1805, the Osage Indians dominated Stoddard County and most of southern Missouri. Their permanent homes were located in western Missouri but conducted three hunts during the year to this area.  They planted gardens of corn, beans, pumpkins, watermelons, and cantaloupe in April.  In May, they would depart on their hunt and continued until August, when they returned to harvest their crops.  They feasted on meat from the hunt and their produce of their harvest until September, then stored the remaining food and departed to hunt again.  they remained gone till December then returned home only to leave again in February or March.

     The Osage Indian men were commonly over 6 feet tall.  Their permanent homes were made by setting forked posts at the corners of a rectangle, about 20 feet apart.  They laid logs across them and then constructed the roof and sides with smaller logs.  All of this was covered with woven reed mats.  Inside, a bench like bed of poles across forked stakes and covered with bear skins extended around three sides of the house.  They sometimes had a raised platform covered with bear skins for honored guests,  During their hunt, they lived in skin houses.

     For weapons, the men used a four foot simple bow of hickory.  The string was made of buffalo or elk sinew and the arrows were tipped with small stone tips until traders in the 1700's brought sheet iron.  War arrows were made so that the shaft would leave the point in the would when pulled out.  The Osage were expert horsemen and marksmen with the bow and arrow, but never adapted to firearms,  They made quivers for their arrows out of cougar skin with the tail hanging down from the top, and cases for third bows out of skin.

     In 1794, Louis Lorimeir, the Spanish Commandant at Cape Girardeau, began encouraging the Shawnee and Delaware Indians to settle in South East Missouri, the purpose of this was to discourage the settlement of Americans, who the Shawnees hated and to counter the threat of the Osage.  The Spanish authorized offered little protection from the Indians.

     Members of the Creek, Cherokee and other southeastern United States tribes were often exiled from their villages for breaking tribal law, they often came to Southeast Missouri and were a real threat to whites living there.

     In 1823, Stoddard County was a wild place, only the hills above the swamps were habitable.  There were two Indian villages, Shawnee Chief Wakepelathy's village in Bloomfield and a village near Leora, composed of Delaware.

     The Shawnee and Delaware in Stoddard County came here in 1816 following a treaty meeting of several tribes in St. Louis.  The early settlers traded with the Shawnee and related Delaware near present Bloomfield and lived peaceably together.  The Shawnee and Delaware of the villages at present Kennett, Bloomfield, and Leora went twice a year to trade furs, bear oil., and honey at  St. Genevieve in the spring and again in the fall. 

     Two Indian trails intersected each other in Stoddard County.  The trails were mere footpaths that were kept worn down by numerous travelers on foot and horseback.  Wild animal used the trails as they followed the best natural routes.  Today many of our roads follow these original routes.  The Natchitoches trail is on to the two that crossed Stoddard County.  It crossed the Mississippi river at Cape, then then the St. Francis river then it crossed at Indian Ford near present Wapapello.  It went on the Poplar Bluff and current River at Pittman Ferry.  This was an infamous route in the early 1800's.  Many murderers and thieves lived along it, preying on helpless travelers as they did on the old Natchez Trail from New Orleans.  The trail as it crossed Stoddard County approximated the rail road through Puxico which was abandoned then the 1960's.

     The Old Shawnee Trail was probably the most famous and most used trail in Southeast Missouri.  It approximated present day Highway 25, following Crowley's Ridge through the swamps, it remained important as a travel route until the completion of the railroad in the late 1800's.  During the civil war, it was crucial to troop movements.