Just Look at Wisconsin's Oldest Building
The blog Supercompressor put together a fantastic list of the oldest standing building in every State o' the Union, with a brief look at the history of each.* Of course I went straight to Wisconsin’s entry and found the Wakely Home of Nekoosa, Wisconsin. Built in 1842 by Robert and Mary Wakely, the Wakely home is a symbol of American pioneerism and western expansion. In 1837 the Wakelys bought a raft full of lumber in New York City and began traveling westward by way of rivers. They sold the lumber in Cincinnati and poled up the rivers in a keelboat to what would be known as Point Basse, the place they would build their home.
Not the most rivieting of travel adventures, but there you have it. We may not have an amazing fortress for our oldest building (as Florida does), or the Taos Pueblo, built sometime between 1000 and 1450 CE (like New Mexico), but the Wakely Mome is a prime example of people striking out west to wild territories to make a new life.
*As Supercompressor says, "...due to some record-keeping discrepancies
there's no doubt some of these might be a bit... disputable."