The charming and stately late 19th century buildings of downtown Woodstock offer confirmation that this is a community devoted to preserving, celebrating and sharing its heritage.  Quaint brick streets and period lighting surround the lovely Park in the Square, where generations of families have gathered to enjoy parades and ceremonies, art fairs and farmer's markets, and summer City Band concerts going back 130 years.

Woodstock was founded in 1844 as Centerville, located in the exact center of McHenry County and designated as the seat of county government.  In 1845, the name was changed to Woodstock, honoring the hometown of settlers from Vermont.  The town was incorporated in 1852, and became a City in 1873. 

In the mid-1800’s, the Chicago & Northwestern railroad arrived, giving local farmers access to large Chicago markets for their cattle, grain and pickles, and allowing Woodstock to attract the Borden Dairy plant, one of the world’s largest at that time.  The early 1900’s brought both Emerson and Oliver Typewriter companies to town, and by 1922, nearly half the world’s typewriters were made in Woodstock.

Early buildings were made of wood and the oldest were largely destroyed during numerous fires.  Two majestic focal points of Victorian architecture remain active anchors to the Woodstock Square Historic District:  the 1857 Old McHenry County Courthouse and the 1889 Woodstock Opera House.  Both buildings are owned and operated by the City of Woodstock and reflect the City’s continuing dedication to historic preservation, arts and culture. 

The Woodstock Opera House was originally built as the City Hall, Library, Auditorium, and Fire Department.  Over several decades, virtually every aspect of the “Gothic” style limestone, brick and terra cotta building has been lovingly restored to its original features.  A favorite venue for performers nationwide, the Opera House presents a year-round schedule of professional theater, dance, music concerts and art exhibitions, attracting thousands of visitors annually to enjoy Woodstock’s unique downtown shops and cafes. 

Legendary actor, director and playwright Orson Welles spent his formative years at Woodstock’s Todd School for Boys and performed his first play on the Opera House stage, now named in his honor.  The Woodstock Players, summer stock theater at the Opera House, launched the careers of acting legend Paul Newman and many others.  Woodstock was "home" to the world's greatest crime fighter, Dick Tracy, as his creator Chester Gould lived here for 50 years, commuting to Chicago six days a week to work on the beloved cartoon strip.  The town starred as Punxsutawney, PA, as the main filming site for the Bill Murray hit movie, Groundhog Day, and Woodstock’s Classic Cinemas movie theater’s main screen has been plaqued as the Harold Ramis Auditorium, reflecting the late director’s affection for his time working in Woodstock.

The Old Courthouse & Sheriff’s House, under major renovation, currently houses restaurant dining with outdoor seating, an art gallery and music studio. In 2015, the Urban Land Institute performed an extensive review of potential development ideas for the future of this building.  Ideas are still being formulated, and planning for the highest and best use of the Old Courthouse continues along with extensive historic preservation repairs and renovation, following years of private ownership and structural deterioration.

Following an enthusiastic community-wide effort by residents wanting to share their beloved community with a national audience, Woodstock was named an All-America City in 1964.  The Old McHenry County Courthouse and the Woodstock Opera House were listed on the National Register of Historic Places in 1974, and the entire downtown area attained landmark status as the Woodstock Square Historic District in 1982. The City obtained Certified Local Government status from the National Park Service in 1998, giving recognition to its excellence in municipal administration.

Other notable achievements reflecting Woodstock’s growing renown as a historical attraction include being one of a Dozen Distinctive Destinations by the National Trust for Historic Preservation in 2007, and being named a Preserve America Community by the White House in 2014.