[3] The city's historic downtown district and turn-of-the-century town square is anchored by the landmark Woodstock Opera House and the Old McHenry County Courthouse.

Early settler Alvin Judd developed a plat for the town, which incorporated a two-acre public square, near which a 2-story frame courthouse and jail were constructed the following year by George C. Dean and Daniel Blair.

[5] In 1895, Eugene V. Debs served a short federal prison sentence in the Woodstock Jail following the 1894 Pullman labor strike in Chicago.

By the time he was released in November 1895 (to great fanfare and before crowds of onlookers assembled in the Woodstock Square), Debs had become a socialist and a national celebrity.

[6] He later ran for the United States Presidency five times between 1900 and 1920 as the candidate for the newly formed Social Democratic Party.

Both factories had active social clubs, baseball teams that competed against one another, and Emerson had a well-regarded band that played at public events.

He also performed at the downtown Woodstock Opera House, where the stage — the site of his American debut as a professional theatre director — is now dedicated to him.

Several original buildings were purchased at auction and reused by Marian Central Catholic High School and Christian Life Services.

[19] The movie brought Woodstock to the attention of location manager Bob Hudgins, who later recommended the town to Harold Ramis for the filming of Groundhog Day.

Although the story is set in Punxsutawney, Pennsylvania, the movie's producers preferred the quintessentially American, but non-specific backdrop of Woodstock Square and its surroundings.

[21] In January 2020, several key actors, including Bill Murray, Brian Doyle-Murray and Stephen Tobolowsky returned to Woodstock to film a Groundhog Day-themed commercial for Jeep.

[23] In August 2018, it was reported that filming had begun in and around the Square for the 2019 HBO series Lovecraft Country from producers J. J. Abrams, Jordan Peele, Misha Green and Ben Stephenson.

[24] A map of Woodstock can be seen on the splash screen for The Jackbox Party Pack 4 game Civic Doodle where the historic square and Illinois route 47 and 120 are clearly visible.

[26] Woodstock was also a primary filming location for the Amazon series Night Sky doubling as the fictional Farnsworth, Illinois.

The Independent also publishes The Torch, a feature-oriented magazine delivered free to all Woodstock residents 8 or 9 times a year.

[28] Woodstock has become an important destination for live music in McHenry County and the region with venues featuring local, national, and international artists.

[31] The three newest buildings, Prairiewood, Creekside and WNHS, were approved in a March 2006 referendum to address crowding in schools due to the area's growth between the mid-1990s and 2008.

Loyola University Chicago owns and operates a large property on Woodstock's eastern edge as its Retreat and Ecology Campus.

According to Woodstock's 2018 Comprehensive Annual Financial Report,[33] the top employers in the city are: Woodstock's railroad station is the penultimate passenger stop on Metra's Union Pacific Northwest Line, which originates from Ogilvie Transportation Center in downtown Chicago and ends in Harvard, Illinois.