Things to Do in Woodstock, Illinois
The best things to do in Woodstock, Illinois, are walking the Groundhog Day filming sites on the Square, catching a show at the 1889 Opera House and shopping the farmers market. Woodstock is the McHenry County seat, a city of 25,630 people northwest of Chicago.
Before Bill Murray, Woodstock was a typewriter town, and in the 1920s its factories made nearly half the world’s typewriters. Orson Welles went to school here from age 10. In 1960 he called Woodstock “my hometown, if it’s anywhere.”
Woodstock Square and the Groundhog Day walking tour
The 1993 film was shot here over 86 days in 1992, with the Square standing in for Punxsutawney, Pennsylvania. The production scouted more than 60 towns before choosing it. Engraved plaques now mark many filming spots, and the Square itself is a National Register historic district.
★ Good to know The tour is self-guided and free any time of year; download the brochure from the Groundhog Days site before you walk.
Woodstock Opera House
This 1889 theater anchors the Square and still books touring acts, plays, dance and comedy. Welles staged the Todd Theatre Festival here in 1934, and the stage now bears his name. Paul Newman, Geraldine Page and Tom Bosley trained here with the Woodstock Players after 1947.
★ Good to know Film fans will know the tower: it’s the one Phil Connors jumps from in Groundhog Day.
Old Courthouse Center
John Van Osdel, Chicago’s first licensed architect, designed the domed 1857 McHenry County Courthouse. Labor leader Eugene Debs was held in the adjoining 1887 jail after the Pullman Strike. Today the restored buildings hold restaurants, shops, event space and the city’s visitor center.
★ Good to know Look up in the old courtroom; its hand-painted ceiling survived the restoration.
Groundhog Days
Woodstock has celebrated its movie every winter since the filming. Woodstock Willie makes his forecast on the Square on February 2. The days before bring screenings, a chili cook-off, a 5K, a pub crawl and guided tours led by locals who worked on the film.
★ Good to know The festival runs in the days leading up to February 2 each year, and in-town lodging books early.
Woodstock Farmers Market
This producers-only market means every vendor grew, raised or made what they sell. It sets up on the Square on Saturdays from May through October and Tuesdays from May through September. Expect produce, meat, cheese, baked goods and flowers, often with live music.
★ Good to know In winter it moves indoors to All Seasons Orchard on select Saturdays from November through April.
Typewriter Trail
The Oliver Typewriter Company helped make Woodstock a typewriter capital. This free, self-guided trail puts 14 antique Oliver machines in cases in downtown storefronts, with a special exhibit at the public library.
★ Good to know It’s seasonal, and the 2026 trail runs through November 23.
All Seasons Orchard and area farms
All Seasons Orchard, on Route 176, has welcomed visitors for more than 30 years, with apples and pumpkins in fall. Heider’s Berry Farm, run by five generations of one family, and Sun Berry Orchards grow berries and fruit nearby.
★ Good to know Picking seasons depend on the crop and the weather, so check each farm’s calendar before you drive out.
Pleasant Valley Conservation Area and Emricson Park
Pleasant Valley covers 2,080 acres and is the largest of the conservation areas around Woodstock. In town, 60-acre Emricson Park is minutes from the Square, and 17-acre Ryders Woods has wooded trails.
★ Good to know The city counts more than 500 acres of parkland, so there’s green space close by whenever you need a break from the Square.
Also in town
Dented Gate Flower Farm grows cut flowers, Woodstock Water Works is the city’s aquatic center, Hennen and Westwood conservation areas have short trails, and the McHenry County Fair is held in Woodstock every year.
Was Groundhog Day really filmed in Woodstock, Illinois?
Yes. The 1993 film was shot in Woodstock from March to June 1992, with the Square playing Punxsutawney, Pennsylvania. The Opera House, the bowling alley and the Moose Lodge all appear on screen.
Can you take the train to Woodstock from Chicago?
Yes. Woodstock is a stop on Metra’s Union Pacific Northwest line, with weekday and weekend service from downtown Chicago. The station is a short walk from the Square.
When is Groundhog Days in Woodstock?
Every year in the days leading up to February 2. Woodstock Willie makes his prediction on the Square that morning, after several days of screenings, tours and parties.
What is Woodstock, Illinois, known for?
Groundhog Day, the 1889 Opera House, Orson Welles’ school years and its past as a typewriter manufacturing center. For more trip ideas, see our small towns in Illinois.
Where to find them
- Woodstock Square and the Groundhog Day walking tour Woodstock Square, Woodstock, IL 60098 Website Directions
- Woodstock Opera House 121 Van Buren St., Woodstock, IL 60098 Website Directions
- Old Courthouse Center 101 N. Johnson St., Woodstock, IL 60098 Directions
- Woodstock Farmers Market Woodstock Square, Woodstock, IL 60098 Website Directions
- All Seasons Orchard 14510 IL Route 176, Woodstock, IL 60098 Directions
- Pleasant Valley Conservation Area 13315 Pleasant Valley Rd., Woodstock, IL 60098 Directions
Plan your trip: for events and current visitor info in Woodstock, see the official visitor site →
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Where to stay in Woodstock
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