Woodstock's town square
The heart of Woodstock is its town square.


Average house price: $234,992
Transportation * * (out of 4) Downtown Chicago is nearly 90 minutes away by train.
Schools * * * The Woodstock school district recently added new elementary, middle, and high schools.
Shopping * * Quaint shops line the town square, and various strip malls are nearby.
Plus: The McHenry County Fair, held here August 4th to 8th, links the town to its rural roots.

In the country’s collective imagination, the ideal small town has a square for a heart. In Woodstock that heart is big enough to accommodate everything from the Supperclub at the Elks and a quilting store to a crêperie and a shop stocked with tie-dyed clothes. After all, a town called Woodstock needs an emporium for psychedelic garb.

In 1992, the brick-lined Woodstock square was Hollywood’s pick to stand in for the idyllic little town in the movie Groundhog Day. With its veterans’ memorial and old-fashioned storefronts, the square didn’t need much prettifying, and the blocks of lovely Victorian homes stretching to the west and south look as if they have been preserved in amber from a time when Woodstock was the bustling mercantile center of rural McHenry County.

But time hasn’t stopped in Woodstock. There is a Starbucks fronting the town square, right next to the opera house, where a teenage Orson Welles began his long onstage love affair with William Shakespeare. A few blocks west, a large, rambling public library rivals the square as a center of activity, particularly in the winter. Sections with a more suburban feel bracket the core downtown area, but around here, all roads lead back toward the square—in one case, via a single-lane tunnel beneath the Metra train line.

A surprising thing happens at this tunnel: Drivers from opposite directions politely wait for each other to get through. Try that in the big city that lies 90 minutes southeast of Woodstock’s town square.


Photograph: Courtesy of the city of Woodstock