In early pioneer days part of Highland and Pleasant Townships were commonly known as Pleasant Prairie in 1852 to 1853. Some of the first settlers who came in and located were: the Stoens, Brunsvold, Arnesons, Mikkel Solberg, Peter Uldvikson, Paul Dagfinson, Bersie Kjomme, Kroshus, Mikkel Walhus, Wennes, Hallend, Luros, Svenung Bergan, and Ole Johnson Svartebratten.

It was about 1853 when the township, which lies in the extreme Northeast part of Winneshiek County, was organized. It is said that the early pioneers drove oxen teams to Decorah and Fremont to get their grain milled. This took one day to go, another to come back, besides one to three days to get their grain ground. Later they patronized the Spring Water mill in Canoe Township, and still later Peter Olson built a mill at Highlandville, but it was discontinued because of waterpower failure.

According to records, the first school in the township was taught by Addison Hoag, in a private house owned by N. N. Kjome. But soon a log schoolhouse was built on the four corners in the center of the township and the first teacher in that school was Samuel Atkins from just over the line in Minnesota.

Highlandville is the only platted village in the township. In 1912 when it had a population of little over 100 residents, besides the post office, it had three general stores, a blacksmith shop, creamery, one doctor, and two farm machine dealers.

On a unusual historical note is an event which took place in the summer of 1848, when a entire tribe of the Winnebago Indians, on their way from Fort Atkinson to Minnesota, camped on a farm in section 17, which is now owned by Alden Wennes. Historians write of the several hundred Indians, their campfire ceremonies and the gala events, which marked the first night away from their old camping grounds at Fort Atkinson. They were on their way to Winona, Minnesota, to be taken by steamboat further up the river to their new home.

Four cemeteries are recorded for Highland Township. The first is in the east edge of section 12 on the Peter Swenson farm; several graves are on the Fawcett farm in section 18; a lone grave of a man by the name of Monro, is just above the former site of the woolen mill in section 25; and unmarked pioneer graves are on the Walter Stoen farm in section 34. The one well-plotted and recorded cemetery is located in section 10 alongside the Highland Lutheran Church.

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