Top 15 Attractions and Activities in Woodstock, IL

When film location scouts seek a charming, small-town setting, Woodstock in Northern Illinois frequently ranks highly on their list.

Although the classic film featuring Bill Murray and Andie MacDowell, Groundhog Day (1993), is set in Pennsylvania, it was primarily filmed in Woodstock, particularly around the picturesque Woodstock Square Historic District.

Woodstock takes pride in its role in pop culture history and hosts an annual festival to celebrate Candlemas (Groundhog Day).

Notably, one famous resident was Orson Welles, who received his education in Woodstock and embarked on his journey as a professional director at the Woodstock Opera House, where the stage bears his name.

1. Woodstock Square Historic District

Woodstock’s primary attraction is its charming townscape which was included on the National Register of Historic Places in 1982. Boasting beautiful historic buildings and cobbled streets, the district showcases the Historic Woodstock Square.

This area features well-maintained landscaping, tall mature trees, and a notable bandstand that has hosted nearly 140 years of summer musical seasons.

Local businesses prosper here, allowing visitors to explore shops selling fabrics, secondhand books, jewelry, apparel, toys, artisanal confections, craft supplies, musical instruments, bicycle accessories, and a variety of other unique items.

Moreover, whether it’s the bandstand, Old Man’s Alley or Ned’s Corner, enthusiasts of Groundhog Day will recognize elements from the film at every turn.

2. Woodstock Opera House

Orson Welles’ inaugural experience as a professional theater director occurred at this striking landmark, which gazes out over the Historic Woodstock Square from its southern side.

Founded in an eclectic style in 1889, the Woodstock Opera House was designed for various administrative purposes, in addition to serving as a performance venue.

Owned by the city since its inception, the building features a diverse program that includes concerts, theatrical performances, classic and independent film screenings, recordings from prominent cultural institutions, musicals, and festivals.

The Woodstock Opera House is prominently featured in Groundhog Day, particularly during a montage where Bill Murray’s character leaps from the tower’s oculus.

3. Woodstock Farmers’ Market

Visit Woodstock on a Saturday morning from April through October, and you will find Historic Woodstock Square bustling with vendors.

The Woodstock Farmers’ Market has recently been recognized as the best in Illinois in the American Farmland Trust’s annual competition. Accompanied by live musical performances, this market features products exclusively from producers, meaning you will be purchasing directly from the grower or maker.

As of the last update, the market has been active for nearly 40 years, presenting a wide variety of vendors specializing in seasonal produce, locally-raised meat, spices, craft beer, sauces and marinades, homemade confectioneries, baked goods, honey, olive oil, pet items, candles, handicrafts, and an extensive selection of prepared foods.

During the winter months from November through March, the market relocates to Building D at the nearby McHenry County Fairgrounds.

4. Old Courthouse

As this article was being composed, one of the pivotal structures at Woodstock Square was undergoing renovations.

The Old McHenry Courthouse, which was established in 1857 and later complemented by the Sheriff’s House & Jail (1887), was in the process of renovations while seeking new occupants.

For thirty years, the Old Courthouse Art Center was a beloved community hub, showcasing artists and facilitating sales.

Currently, the Public House of Woodstock, serving contemporary American cuisine, occupies part of the building and features an attractive patio during the summer months.

John Hughes, known for filming many of his productions in the Chicago suburbs, utilized this landmark as a backdrop for a scene in Planes, Trains and Automobiles (1987) when the characters Neal and Del have their rental car towed.

5. Illinois Railway Museum

Given that the railroads significantly contributed to the development of Illinois in the 19th century, it is only fitting that the Illinois Railway Museum houses the largest collection of historic railway equipment in the United States.

Spanning 100 acres and preserving various historic structures, this museum is located ten miles from Woodstock in the small village of Union.

The highlight of the museum is a 4.6-mile demonstration railroad where visitors can enjoy a ride on a steam train, diesel train, trolley bus, or electric streetcar.

A schedule of operations can be found on the website, including activities tailored for children, allowing visitors to select the event or experience that suits them best.

Additionally, visitors can explore the extensive fleet of historic locomotives, passenger cars, and streetcars while observing restoration projects in progress.

6. Pleasant Valley Conservation Area

The McHenry County Conservation District oversees this 2,000-acre natural area, entirely devoid of roads.

This conservation area has been acquired in phases since 1994 and boasts a range of habitats accessible through five miles of hiking and nature trails.

Highlighted features include a prairie rich in wildflowers during the summer, expansive oak woodlands, and an untouched wetland region.

The area has recorded over 270 plant species, including 13 rare varieties, and it provides a habitat for wildlife such as foxes, hawks, salamanders, deer, turtles, and a diverse array of warblers.

7. Emricson Park

Emricson Park serves as Woodstock’s primary community park, situated approximately a mile west of the square. The expansive park offers excellent facilities for a variety of sports, including baseball/softball, soccer, and tennis.

The recreation department provides a public outdoor swimming pool located at the northern end of the park. Additionally, the park features playgrounds catering to different age groups and an extensive network of trails that also includes picnic areas with tables and seating.

Emricson Park is also the venue for Woodstock’s July 4th fireworks display, inviting visitors to bring along a chair or blanket for comfort.

8. All Seasons Orchard

With orchards in every direction, autumn is a splendid season to explore Woodstock. With 15,000 apple trees, All Seasons Orchard employs Integrated Pest Management techniques to reduce its environmental footprint.

During the harvest season, spanning from Labor Day weekend through October, the orchard transforms into a genuine attraction for visitors.

Guests can pick from 12 different apple varieties as they come into season, along with six pumpkin varieties available in the pumpkin patch.

Additionally, All Seasons Orchard features a 10-acre corn maze, a zip line, a petting zoo with a variety of animals, and a farm market, restaurant, and concession stand that utilize the farm’s own produce.

The apple cider donuts are a notable specialty, available for purchase at three different locations throughout the farm.

9. Woodstock Water Works

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

Typically open from Memorial Day weekend until the conclusion of the summer school break, Woodstock Water Works caters to both serious swimmers and families looking to enjoy the warm weather.

The facility features an eight-lane lap pool with two diving boards, in addition to a leisure pool with a beach entry and a double flume slide.

For families with young children, there is a tot pool and a designated play area. The park also offers ample green space for picnics and relaxation, along with a food court.

10. Groundhog Days

Although Punxsutawney Phil resides over 500 miles away in Pennsylvania, Groundhog Day holds a unique significance for Woodstock more than 30 years after the film was produced here.

In the five days leading up to Candlemas (Groundhog Day), Woodstock commemorates the film through a vibrant schedule of activities and entertainment.

These festivities include guided tours of filming locations, a special breakfast, a chili cook-off, dance events, and screenings of this classic film at the Woodstock Theatre.

The festival culminates in the Groundhog Day event, where attendees gather to determine if spring will arrive early or if winter will linger for six more weeks.

11. Classic Cinemas Woodstock Theatre

This location on Main Street has housed a movie theater since 1911. Originally known as the Princess Theatre, it was demolished in the 1920s and replaced by the Miller Theatre, which hosted both films and vaudeville performances.

This building laid the foundational framework for today’s Woodstock Theatre, which was divided in 1979 and later annexed with a neighboring building that was previously a theater from 1912.

The retro marquee was introduced in 1991, and the interiors underwent renovation in 1998 when Classic Cinemas assumed management.

With eight screening rooms, the cinema featured in Groundhog Day as The Alpine, the venue where Bill Murray’s character watches a movie. A noteworthy perk includes free refills on soda and popcorn regardless of the size purchased.

12. Heider’s Berry Farm

The Heider family has been cultivating this land northeast of Woodstock for five generations. For many decades, it operated as a traditional Midwestern farm, producing corn, oats, hay, and raising livestock; however, in the 1970s and 1980s, it evolved into the largest berry farm in Illinois.

Visitors can enjoy the experience of picking strawberries (available in June and September) and raspberries (available in July and September) in the summer and fall months.

Both pick-your-own and pre-picked berries can be acquired from the farm shop, which also offers homemade jams and artistically crafted wood products.

13. McHenry County Fair

Opening its doors in 1949 on the eastern outskirts of Woodstock, the McHenry County Fairgrounds has been the venue for the county fair ever since.

This fair first took place from 1854 until 1924 before ceasing operations and then restarting in Woodstock. Held over six days in August, the event remains deeply connected to agriculture, showcasing livestock, non-livestock 4-H exhibits, and education displays focused on farming and conservation.

In addition to its agricultural roots, the fair offers a wealth of family-oriented entertainment, including talent shows, antique contests, a demolition derby, live music, carnival rides, and a diverse selection of food and drink options.

14. Donley’s Wild West Town

This recreated Wild West town, located just south of Union, brings to life characters from various backgrounds. Donley’s Wild West Town features an array of traditional attractions, including a saloon, print shop, blacksmith shop, and a jail.

Visitors can ride a narrow gauge train throughout the town, engage in gold panning at the Sweet Phyllis Gold Mine, and enjoy stunt shows performed by trained professionals.

Children can also experience a roller coaster, pony rides, various concessions, and a gift shop offering Wild West memorabilia.

15. Fair Diddley Craft Show

If you are planning a visit to Woodstock in early summer, you will not want to miss the highly attended art fair held at the Historic Woodstock Square on the third Sunday in May.

Artists from near and far converge on Woodstock for this juried event, showcasing exceptional talents in a range of mediums including fine art, woodcarving, jewelry, ceramics, textiles, blown glass, and much more.

With over 350 exhibitors participating each year, some even traveling from as far as California, Fair Diddley has been a delightful tradition for more than 50 years. Organized by the McHenry County Mental Health Resource League, proceeds from the event support various charitable causes throughout the county.