The Woodstock Square — A Brief History Lesson

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The Woodstock town square is the most recognizable location in our city, as well as a gathering place and cultural center. For residents and visitors alike, when we hear Woodstock, it is the Square, with its Victorian buildings and brick streets, that we picture in our minds.

On this Throwback Thursday, let’s take a quick look at the history of the Square. In a future post, we’re going to take a field trip to check out what the Square has to offer. But, as anyone who has been to school knows, you have to do some homework before you get to go on the field trip.


In 1844 Alvin Judd platted a new town in the center of McHenry County, and named it Centerville. The plat contained a central square oriented to the compass points, with streets originating at the centers of the four sides. The whole square was surrounded by a rectangular grid. The following year, the name of the village growing around the Square was changed to Woodstock, at the suggestion of an early settler to honor his home town of Woodstock, Vermont.

Woodstock, Illinois, became the county seat of McHenry County. A courthouse was built on the Square in 1857 at a cost of $47,000. The Square itself was graded and planted with elm trees in 1858-9. These photos from the 1860s show what it looked like at the time.

old courthouse

Note: A tornado in 1967 destroyed all of the trees in the Square.

square 1864

In 1887 the county built a jail next to the courthouse. Two years later, work began on the Square’s opera house. This imposing Romanesque-styled building originally held, in addition to the 64-seat theater, the city hall, the fire department, and the public library.


The streets were not paved with their signature bricks until 1912.

bricks 1912


Finally, let’s end this mini-lesson with a then-and-now comparison.

Here is the Square decorated to commemorate the death of President Ulysses S. Grant in 1885.

square 1885 grant

And here is the same place last summer during the Fair Diddley craft show.

FD square


This is very much how the Square will look when we visit it next week for Part 2 of this post.


  1. Judi Koeller says

    As a recent transplant to Woodstock, I thank you for this interesting history lesson, Caryl!


  2. Pingback: Summer Saturday on the Square | Home Sweet Abbey

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