The earliest people to walk on the lands around Winona were the Paleo-Indians. A transitional period between cultures was known as the Archaic Period. The use of pottery occurred during the Woodland Cultures.

The Paleo-Indian period was from about 9,500-7,500 B.C. in the Upper Mississippi Valley and around the areas of Winona , Minnesota. These people were known as "Big Game Hunters" by archeologists. They may have hunted animals such as mammoth, mastodon, and great bison along the glacial front. It is also felt that because the Paleo-Indians would continually move in search of food that they were a Nomadic culture.

In the area around Winona, in both Minnesota and Wisconsin, archeologists have found fluted and unfluted spear points near bones of large animals. These spears were some of the first stone tools found in and around this area. One of the biggest finds was south of Minnesota, in Iowa, at a complex called Clovis. Other sites in the area are usually very small and scattered.

The archaic period took place from about 7,500-500 B.C. around the areas of Winona. Archaic cultures were known as "Hunters and Gatherers" by archeologists. It is felt that archaic bands of people started to settle at regular sites during different seasonal periods. Communal cemeteries started to be seen during this period which reinforced the idea that the people were starting to call different locations home instead of moving around the lands continually.

The establishment of networks may have occurred around this time as marine shell, copper, and exotic stone materials started to be used in different settings. Spear points had progressed into an array of side-notched, stemmed, and corner-notched points.

The Woodland period occurred from about 500 B.C. to 1000 A.D. The first ceramic pottery and the use of burial mounds appeared in this area during this period. Because of this, archeologists refer to the Woodland culture as"Potters and Mound builders". A large number of mound sites are located at Perrot State Park in Wisconsin. Scattered throughout the hills of the park there are also effigy mounds, which are shaped like animals.

Woodland cultures made heavy use of fishing, continued hunting of deer and bison, and the gathering of native grains, corn, and beans for food. Late Woodland cultures introduced the area to the bow and arrow and triangular spear heads. Exotic pottery developed during the Woodland Period. Fancy designs on thinner pots became very popular.

It is not actually known when the first people, who were known as the Dakota or Sioux, arrived in this area. During the era between about 1500 to 1700 A.D. the culture known as the Mound Builders had blended into other Midwestern Indian groups. The area in which Winona is located may have been occupied by several Indian groups including the Fox, the Sauk,the Iowa, or the Winnebago.

We do know that the early French explorers in the area encountered the Dakotas along the Upper Mississippi from the Iowa border to St. Paul. The Indian band that lived along the river in Winona was part of the Dakota nation which was divided into three major groups according to location or family lines. These were the Eastern or Santee, the Nakota or Middle and the Western or Lakota. The Santee were subdivided into three groups: the Mdewakantonwan, the Wahpekutes, the Wahpetons, and the Sissetons. The Mdewakantonwan Dakota band of Chief Wapasha were thought to have moved to the area south of Winona near the Iowa border during the the late 1600's or early 1700's.

The four divisions of the Santee originally lived in the north central part of Minnesota but when the first whites began to move in, many of these people had begun to move to different areas of the state. They moved for various reasons such as food scarcity, pressure from other tribes moving west with the white man (especially the Ojibway and the Cree) and other causes which are not all known. The Mdewakantonwans moved down along the Mississippi Valley and one band in particular settled in the area which is now known as Winona.

The leader of this band was known as Chief Wapasha II. He was the son of the great Mdewakantonwan chief Wapasha whose band roamed the area from the Upper Iowa River to the Root River in southeastern Minnesota. When Lt. Zebulon Pike visited the Winona area, Chief Wapasha I was an old man with a great reputation among his people. Wapasha II is believed to have moved his band to the Winona area around 1806-1810. Major Stephen Long, traveling up the Mississippi in 1817, found Wapasha II's band well established in what was called Wapasha's Prairie or the site of present day Winona.

Wapasha's people lived a difficult life. Finding shelter and food-gathering occupied most of their time. Early white settlers to the area noted that the people were kind and generous. They took great pride in both group and individual accomplishments. Food was obtained in several ways- most common of which was hunting and gathering. Since the big game animals of the prairie were beginning to become scarce, hunting for them was a big task. Usually the hunters would have to travel many miles to find deer, elk, or buffalo. Wapasha and his people went to great lengths to preserve the wildlife that remained in the valley. He was a conservationist who managed the wildlife herds and flocks with great care. In the spring, the people would set great fires to burn off old growth and help the new grasses get started. Some of the plants which the people lived on that grew wild in the area were strawberries, blackberries, grapes, nuts, wild tubers and a variety of bulbs. They also practiced some agriculture and the most popular crop they raised was corn.

Wapasha's people lived in teepees or bark-covered lodges along the river bottoms. They wore bright clothes and jewelry. They held many ceremonies and sporting events. They especially loved the game of Lacrosse, which they played in great numbers and with violent enthusiasm. When someone died the body was placed on a raised platform and left there until it decomposed and dried up. Like all Dakota tribes, the people of Wapasha's Prairie believed they were created by the Great Spirit and so was the sacred stone found in western Minnesota called "pipestone." With this stone they made large colorfully decorated pipes which they smoked for almost any special occasion such as meetings, ceremonies, or feasts.

The Indians named the area now known as Winona "Keoxah," which means "The Homestead" in Dakota. One of the first whites to visit this area, Mr. George Clarke, described Wapasha's Prairie as Òtheir summer home, a barren prairie, devoid of trees, on which about twenty fixed lodges and cabins stood. [There]...were at least ten acres of scaffolding and graves. Beyond this was their playground, which consisted of a pole twenty feet high with a flag on top, and a circle of fifty feet in diameter at its base with a granite rock as an altar, where it was said, sacred dances were held. Down toward the river or slough were found large buildings sixteen by sixty feet on the ground, and about six feet high at the eaves, and ten feet to the top of the ridge poles, covered with elm bark for a roof. Those buildings were the summer houses parallel with each other; on the insides were raised platforms, upon which the Indians slept " (Hanson, p. 2).

The first steamship to come up the Mississippi to the area was "The Virginia." The people on board felt that the area was too low and not suitable for settling. However, in the fall of 1851 when Captain Orrin Smith came ashore and began the establishment of a settlement, Wapasha's Prairie saw the beginning of the end for the Dakota of Wapasha's band. The decline of their traditional lifestyle matched the rise of the budding community now known as the city of Winona. Treaties in 1850 and 1851 culminated the end of the Dakota culture in Minnesota. The Mendota Treaty of 1851 passed Wapasha's Prairie into the hands of the whites. As the buildings were being built where Wapasha and his people lived, the Indians were moving to reservations. By 1853 the removal of all Indians from their homelands was in full swing. It was a long process and it was interrupted frequently by many who did not stay on the reservations but returned to the area.

Contact between whites and Indians during this period was frequent and sometimes inhospitable. Many whites saw the Indians as dirty beggars who would show up at their doors and demand food or money for liquor. Often, it was reported, whites would be disturbed by the late night ceremonies when drums were being played. One of the regular sights in the young community was a member of Wapasha's band named Tamaha. He would stop whites as they passed and show his medals that he had received from Lt. Zebulon Pike. He would charge passerbys money to see them. By the end of the 1850's, the Dakota's were gone from Wapasha's Prairie.