Wisconsin in the late 1800s was all about farming. The dream of many of its settlers was to clear land and farm. Not so with my great-grandfather, Leroy Dilley. He chose to be a tradesman and his trade of choice was painting.

I’m not sure why he chose painting. As a young man, he started out as a lumberjack, working in the lumber camps of north-central Wisconsin. But marriage and family probably gave him the incentive to find a less dangerous line of work. Wisconsin was becoming more settled by the 1890s. People were building permanent, milled lumber homes and businesses. All these buildings needed painting and my great-grandfather was the man to do it.

Leroy the Lumberjack – the shadowy figure in the middle of the log pile.

Leroy and his wife Tillie had both lived in Symco, Wisconsin since childhood. They spent the first 10 years of their married life there as well. Leroy must have started out in the painting business right in Symco, but the town was so small opportunities were few and far between.

While trying to find out more about my great-grandparents, I came across an article in the Clintonville Tribune from November 1903. Leroy had traveled to western Wisconsin looking for painting opportunities. Unfortunately, the trip wasn’t successful in finding new business, but he did find something else! An established painting company that invited him to become a partner. The company was in Clintonville, just 14 miles away from Symco.

Commuting in those days didn’t exist. Travel was cumbersome and expensive, so most people lived where they worked. Even though Clintonville was close to Symco, the new business required the family to move. There was no Mayflower Moving Van or Budget Truck to move them in March of 1904. And it wasn’t exactly summer. Nope, the cold temperatures and thick layer of snow on the ground meant that they would be moving their household by sleigh. Furniture and boxes of odds and ends rode in a sleigh just fine, but what about the kids?

At the time, Leroy and Tillie had 3 young girls, my great-aunts Iva, Sylvia, and Hazel, ages 7, 5, and 2. I’m sure they liked riding around in wagons and sleighs, but not 14 miles in freezing temperatures. Tillie must have started by bundling the girls up in layers of clothing (ala Christmas Story snowsuit style). But, that wasn’t enough. To make sure the girls stayed warm on the trip, Leroy and Tillie packed all three in barrels of straw and loaded them on the sleigh with the rest of the cargo. My aunts remembered this trip very, very well. How do you forget being packed in a barrel of straw? They never told us if it was comfortable, but they must have kept warm because they made it to Clintonville!

The Dilley family in 1907, three years after moving to Clintonville.

Leroy became a partner in Thorn and Dilley Painting and Wallpapering. He worked in the painting business for the next 30 or so years. As for the move, we always thought it was hilarious that Tilly and Leroy packed their kids in barrels of straw. Put them on the sleigh right next to the rocking chair and dining room table. Imagine unloading and suddenly seeing two little eyes looking up at you. It gives new meaning to the question “Got everything packed, honey?”

Interested in another fun Dilley story?
Read about my Grandma Grace and the Ugly Green Dress.



Image Credit: Images from the records of Gerald and Ruth Dilley.

Header Image by Free-Photos from Pixabay.