15 Best Things to Do in Woodstock (IL)

Written by Jan Meeuwesen
Updated on
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When movie location scouts need a cozy, small-town setting, Woodstock in Northern Illinois is often top of the list.

Although the Bill Murray and Andie MacDowell Classic, Groundhog Day (1993) is set in Pennsylvania, it was filmed right here in Woodstock, mostly around the quaint Woodstock Square Historic District.

Woodstock is pleased with its place in pop culture history, and puts on an annual festival to coincide with Candlemas (Groundhog Day).

A real, famous resident was Orson Welles who was educated in Woodstock and took his first steps into professional directing at the Woodstock Opera House, where the stage is named after him.

1. Woodstock Square Historic District

Woodstock Square Historic DistrictSource: Nejdet Duzen / shutterstock
Woodstock Square Historic District

Woodstock’s greatest attraction is the adorable townscape that was listed on the National Register of Historic Places in 1982. With its lovely old buildings and brick-paved streets, the district converges at the Historic Woodstock Square.

This space has cute formal landscaping, tall mature trees and an iconic bandstand that has staged almost 140 years of summer band seasons.

Small businesses thrive here, and you can hop from shop to shop, selling fabrics, secondhand books, jewelry, fashion, toys, artisan confectionery, craft supplies, musical instruments, bicycle accessories and lots of other specialty items.

And whether it’s the bandstand, Old Man’s Alley or Ned’s Corner, fans of Groundhog Day will recognize something from the movie at every turn.

2. Woodstock Opera House

Woodstock Opera HouseSource: Nejdet Duzen / shutterstock
Woodstock Opera House

Orson Welles’ debut as professional theatre director took place at this arresting landmark, overlooking the Historic Woodstock Square from its south side.

Constructed in an Eclectic style in 1889, the Woodstock Opera House was intended for multiple administrative uses, as well as being a performance space.

The building has been owned by the city for its entire history and presents a rich program of concerts, theatre performances, classic and independent movie screenings, recordings from major cultural institutions, musicals and festivals.

The Woodstock Opera House is prominent in Groundhog Day, memorably in a montage in which Bill Murray’s character leaps from the tower’s oculus.

3. Woodstock Farmers’ Market

Farmers MarketSource: Matej Kastelic / shutterstock
Farmers Market

Come to Woodstock on a Saturday morning April through October and Historic Woodstock Square will be lined on all sides by vendors.

The Woodstock Farmers’ Market has recently ranked as the best in Illinois in the American Farmland Trust’s annual contest. Soundtracked by live music, this is strictly a producers only market, so you know you’ll be buying directly from the grower or maker.

At the time of writing, the market had been going for nearly 40 years, with a large directory of vendors specializing in seasonal produce, farm-raised meat, spices, craft beer, sauces/marinades, homemade candy, baked goods, honey, olive oil, pet products, candles, handicrafts and a wide choice of prepared foods.

November through March the market switches to its winter location, Building D at the nearby McHenry County Fairgrounds.

4. Old Courthouse

Old Courthouse, WoodstockSource: Teemu008 / Flickr | CC BY-SA
Old Courthouse

When we wrote this article one of the anchors for Woodstock Square was going through some changes.

On the northwest side, the Old McHenry Courthouse, constructed in 1857 and later joined by the Sheriff’s House & Jail (1887), was being renovated and seeking new tenants.

For three decades one of the main occupants was the Old Courthouse Art Center, a much loved hub and sales point for community artists.

An ongoing tenant is the Public House of Woodstock restaurant (contemporary American), with a cute patio at the front in summer.

John Hughes, who shot most of his films in the Chicago suburbs, used this landmark as a backdrop for a scene in Planes, Trains and Automobiles (1987) when Neal and Del get their rental car towed.

5. Illinois Railway Museum

Illinois Railway MuseumSource: Carlos Yudica / shutterstock
Illinois Railway Museum

In a state that owes a lot of its 19th-century development to the railroads, it makes sense that the Illinois Railway Museum should have the largest collection of historic railway equipment in the United States.

On 100 acres, preserving numerous historic structures and powered by a multi-talented team of volunteers, this attraction is ten miles out of Woodstock by the tiny village of Union.

The center of attention here is the 4.6-mile stretch of demonstration railroad for a ride on a steam train, diesel train, trolley bus or electric streetcar.

An operating schedule is posted on the website and includes activities for children, so you can pick the event or experience that’s right for you.

The remainder of a visit can be spent inspecting the wonderful fleet of historic locomotives, passenger cars and streetcars, and watching restoration efforts in progress.

6. Pleasant Valley Conservation Area

Pleasant Valley Conservation AreaSource: Ken Schulze / shutterstock
Pleasant Valley Conservation Area

The McHenry County Conservation District maintains this 2,000-acre expanse of nature, completely free of any roads.

The district purchased Pleasant Valley in blocks from 1994 onwards, and there’s a diversity of habitats to be enjoyed along five miles of hiking and nature trails.

These include prairie, brilliant with wildflowers in summer, as well as grand oak woodlands and a wetland area that has never been cultivated.

More than 270 plant species have been recorded at Pleasant Valley, 13 of them rare, and the conservation area supports animals like foxes, hawks, salamanders, deer, turtles and a variety of warblers.

7. Emricson Park

BaseballSource: David Lee / shutterstock

Woodstock’s main community park is a mile or so west of the square. Emricson Park is massive and has first-class amenities for a range of sports, including baseball/softball, soccer and tennis.

The recreation department’s public outdoor pool is at the north end (more next), there are playgrounds for different ages, and you can walk or cycle along an extensive trail system, well served with tables and picnic areas.

Woodstock also hosts its July 4th fireworks at Emricson Park and you’re invited to bring a deckchair or blanket.

8. All Seasons Orchard

All Seasons OrchardSource: All Seasons Apple Orchard / Facebook
All Seasons Orchard

With fruit farms in every direction, fall is a wonderful time to be in Woodstock. With 15,000 apple trees, All Seasons Orchard uses Integrated Pest Management to minimize its impact on the environment.

During the harvest season, Labor Day weekend through October, the farm becomes a genuine visitor attraction.

You can pick 12 different apple varieties as they come into season, as well as six varieties of pumpkins at the pumpkin patch.

During this time, All Seasons Orchard also features a 10-acre corn maze, a zip line, a petting zoo with lots of cute animals, as well as a farm market, restaurant and concession stand, all using the farm’s own delicious produce.

The apple cider donuts are a specialty and can be purchased at three different spots around the farm.

9. Woodstock Water Works

Swimming PoolSource: Roman Samborskyi / shutterstock
Swimming Pool

One of the best things about summer in Woodstock is this public outdoor pool aquatic center, on the north side of Emricson Park.

Generally open Memorial Day weekend to the end of the school summer break, Woodstock Water Works caters to serious swimmers as much as families here to enjoy the weather.

There’s an eight-lane lap pool with two diving boards, as well as a leisure pool with beach entry fed by a double flume slide.

For parents with smaller children there’s a tot pool as well as a tot play lot. The park has lots of green space for picnics and relaxing, as well as an entire food court.

10. Groundhog Days

Punxsutawney Phil may live more than 500 miles away in Pennsylvania, but Groundhog Day has a special meaning for Woodstock 30+ years after the movie was shot here.

In the five days leading up to Candlemas (Groundhog Day), Woodstock celebrates the movie with a lively schedule of activities and entertainment.

There are guided tours of the shooting locations, a special breakfast, chili cook-off, dances and screenings for this classic film at the Woodstock Theatre.

The festival builds up to Groundhog Day to discover if there will be an early spring or six more weeks of winter.

11. Classic Cinemas Woodstock Theatre

Classic Cinemas Woodstock TheatreSource: Nejdet Duzen / shutterstock
Classic Cinemas Woodstock Theatre

There has been a movie theater at this site on Main Street since 1911. First came the Princess Theatre, which was knocked down in the 20s and replaced with the Miller Theatre, for both movies and vaudeville.

That building forms the basis for today’s Woodstock Theatre, which was split in half in 1979 and later annexed the neighboring building, itself a former theatre from 1912.

The retro-style marquee is from 1991, and the interiors were remodeled in 1998 when Classic Cinemas took over.

Today there are eight screens, and the cinema made an appearance in Groundhog Day as The Alpine, where Bill Murray’s character watches a movie. One of the many perks here is the free refills on soda and popcorn no matter what size you purchase.

12. Heider’s Berry Farm

Heider’s Berry FarmSource: Rajesh Vijayakumar / shutterstock
Heider’s Berry Farm

The Heiders have been farming this land northeast of Woodstock for five generations. For decades this was a typical Midwestern farm, with corn, oats, hay and livestock, but was transformed in the 70s and 80s into the largest berry farm in the state.

Come in the summer and fall for strawberries (June and September-frost) and raspberries (July and September-frost).

You can pick your own or get them pre-picked from the farm shop, which also sells homemade jam and elegant handcrafted wood items.

13. McHenry County Fair

FairSource: zzphoto.ru / shutterstock

The McHenry County Fairgrounds opened in 1949 on Woodstock’s eastern outskirts, and have hosted the county fair ever since.

The original fair ran from 1854 to 1924 before shutting down and restarting in Woodstock. Six days in August, the event is still rooted in agriculture and you’ll see livestock and non-livestock 4-H, Open and Junior Open shows, as well as education displays centered on farming and conservation.

These are combined with a big helping of family entertainment, from talent and antique contests to a demolition derby, live music, carnival rides, craft vendors and food and drink for every palate.

14. Donley’s Wild West Town

Donley’s Wild West TownSource: Donley's Wild West Town / Facebook
Donley’s Wild West Town

The Wild West comes alive at this recreated town just south of Union. Home to characters from all walks of life, Donley’s Wild West Town has a number of old-time amenities like a saloon, print shop, blacksmith’s shop and jail.

You can ride a narrow gauge train through the town, try panning for gold at the Sweet Phyllis Golf Mine and watch stuntmen having showdowns in the street.

There’s also a roller coaster for children, pony rides, concessions and a gift shop selling wild west memorabilia.

15. Fair Diddley Craft Show

Fair Diddley Craft ShowSource: frantic00 / shutterstock
Fair Diddley Craft Show

If you’re planning a visit to Woodstock in early summer there’s a well-attended art fair at Historic Woodstock Square on the third Sunday in May.

Artists from near and far come to Woodstock for this juried event, showcasing exceptional talent in anything from fine art to woodcarving, jewelry, ceramics, textiles, blown glass and much more besides.

There are upwards of 350 exhibitors every year, traveling from as far away as California. Fair Diddley has been going for more than 50 years now, and is organized by the McHenry County Mental Health Resource League, with profits going to various good causes around the county.


15 Best Things to Do in Woodstock (IL):

  • Woodstock Square Historic District
  • Woodstock Opera House
  • Woodstock Farmers’ Market
  • Old Courthouse
  • Illinois Railway Museum
  • Pleasant Valley Conservation Area
  • Emricson Park
  • All Seasons Orchard
  • Woodstock Water Works
  • Groundhog Days
  • Classic Cinemas Woodstock Theatre
  • Heider’s Berry Farm
  • McHenry County Fair
  • Donley’s Wild West Town
  • Fair Diddley Craft Show