The Woodstock Square Historic District is located in the county seat of McHenry County, Illinois, which is Woodstock. The district is located in downtown Woodstock and has been listed on the National Register of Historic Places since 1982.Within the district two of Woodstock's other Registered Places can be found, Woodstock Opera House and the Old McHenry County Courthouse.

The square consists of historic buildings and is anchored by two key structures, the Old McHenry County Courthouse and the Woodstock Opera House. Most of the other buildings on the square are privately owned and kept up, housing numerous small businesses, including restaurants and shops. The streets of the square are one way and paved with brick, they square off a large public park which features two gazeebos and war memorials. During the winter the square and its buildings and trees are adorned with lights.

The Woodstock Square is host to a number of festivals and events throughout the year. Some the events include Harvestdays, Old Time Fiddlers Competition and Groundhog Days, celebrating the city of Woodstock's role in the 1993 film Groundhog Day. Groundhog Day was filmed on location in Woodstock, Illinois, the city portrayed Punxsutawney, Pennsylvania in the film.