11 Best Things To Do In Woodstock, Illinois

things to do in woodstock illinois
| 3 min read

Woodstock is a rural getaway located nearly 50 miles (80 kilometers) from Chicago. This small-town retreat is full of experiences for a family, couple, or even a lone traveler. You’ll feel at home with the hospitable locals and the open, creative feel of Woodstock. Whether you’re looking for a culturally enriching adventure, a leisurely retreat, or an outdoor escape, there’s so many things to do in Woodstock, Illinois for everyone!

1. Dufield Pond Conservation Area

Editor's Note: Photo taken from the establishment's official social account

If you want to fully enjoy the great outdoors on your visit to Woodstock, Illinois, check out Dufield Pond Conservation Area. This outdoor recreational area features 1.2 kilometers (0.75 miles) of hiking trails that wind along a forest of towering oak trees, through steep topographies, until you reach a sightseeing area where you can fully appreciate the natural beauty of the place.

Aside from hiking, Dufield Pond Conservation Area is also known to provide a great fishing experience for both locals and visitors alike. That’s because the conservation area also features a 7-acre (2.8-hectare) lake that supports a huge number of popular game fish including crappie, largemouth bass, bluegill, channel catfish, yellow perch, and more.

Dufield Pond Conservation Area

Address: 11750 Country Club Rd, Woodstock, IL 60098, United States

Website: Dufield Pond Conservation Area

Opening hours: Sunrise to Sunset (daily)

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2. Kishwaukee Park

Editor's Note: There's no photo available at the time of writing

Have an intimate date with Mother nature at Kishwaukee Park. This beautiful piece of land is part of the headwaters and watershed of the Kishwaukee River and features sedge meadows, wetlands, savannas, and grasslands—all supporting various prairie plants and wildflowers. Aside from its natural beauty, the area is also known to support different varieties of wildlife including grassland birds, dragonflies, butterflies, and so much more.

Visitors can fully take in these amazing sceneries via 1.72 miles (2.8 kilometers) hiking trails on dry land and over wetlands on a boardwalk.

Kishwaukee Park

Address: Woodstock, IL 60098, United States

Website: Kishwaukee Park

Opening hours: Sunrise to Sunset (daily)

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3. Woodstock Water Works

Editor's Note: There's no photo available at the time of writing

Posted by Woodstock Water Works on Tuesday, September 29, 2015

Thinking about what to do in Woodstock, IL, with your kids? Here’s one that will surely be fun for kids of all ages. Woodstock Water Works is a local favorite water park located in the northwest corner of Emricson Park. This family fun destination features a recreation pool that has a double flume slide.

Aside from this fun attraction for the kids and kids at heart, the water park also features an eight-lane lap pool with a 3-meter diving board, a baby pool, a toddler play area, two shelters, picnic grounds all around, and a concessionaire that sells tasty bites and drinks.

Woodstock Water Works

Address: 1313 Kishwaukee Valley Rd, Woodstock, IL 60098, United States

Website: Woodstock Water Works

Opening hours:1pam - 6pm (daily)

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4. Read Between the Lynes Bookstore

Editor's Note: Photo taken from the establishment's official social account

Posted by Read Between The Lynes on Monday, May 2, 2022

Looking for a quirky, small-town shop full of personality? You can go book shopping in Woodstock, IL, in this wonderful bookstore. Read Between the Lynes offers events, games, and book-inspired treats! This bookstore is easily accessible, as it’s located in downtown Woodstock. The staff is friendly and open, aiming to engage many in their events. If you’d like to become a part of the community, this is a shop for you.

Read Between the Lynes Bookstore

Address: 111 E Van Buren St., 60098 Woodstock, IL

Website: Read Between the Lynes

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5. Woodstock Farmer's Market

Source: Photo by Flickr user Tony Alter used under CC BY 2.0

The Woodstock Farmer’s Market presents an opportunity to socialize with the locals and get to know some of the producers that power small-town Woodstock. There are many different products and homemade goods to be found, plus it’s conveniently located at Woodstock Square. The market takes place in the months of May to October on Tuesdays and Saturdays, offering plenty of opportunities to stop by!

Woodstock Farmer's Market

Address: 100 Johnson St., 60098 Woodstock, IL

Website: Woodstock Farmer’s Market

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6. Woodstock Folk Festival

Editor's Note: Photo taken from the establishment's official social account

You won't want to miss the Heather Pierson Acoustic Trio at this Sunday's 31st Annual Woodstock Folk Festival (2...

Posted by Woodstock Folk Festival on Wednesday, July 13, 2016

The Woodstock Folk Festival is one of the most popular events in Woodstock, IL. It is a unique event unlike many. Bringing culture and livening the spirit of acoustic music, a music festival is a day-long event every third Sunday of July. It began in 1986 and was intended to be a one-time event. However, the strong support of the Woodstock Folk Festival has brought it back each year since.

In the above image, instrumentalist and vocalist, Joe Ravo, and multi-instrumentalist, Allison Scola, have performed at Woodstock, featuring their creative, original music with influences from Sicilian and Italian folk. Looking for an event thick with culture and fun? Check out the festival and become a part of an event that is truly unlike one you’ll find almost anywhere.

Woodstock Folk Festival

Address: 205 W Todd Ave, 60098 Woodstock, IL

Website: Woodstock Folk Festival

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7. Woodstock Square Historic District

Woodstock Town Square
Source: Photo by Flickr user Teemu008 used under CC BY-SA 2.0

Woodstock Square is a historic area that features original dining, shopping, and entertainment experiences. The town square is also home to the antique stores, book stores, a variety of dining such as Papa G’s, as well as many events like the Art Walk. Woodstock Square is best known for its appearance in the movie, Groundhog Day, which also happens to be a popular Woodstock IL holiday events. However, it’s more than just a Hollywood backdrop; Woodstock Square will make you feel right at home on your vacation!

Woodstock Square

Address: 205 W Todd Ave, Woodstock, IL

Website: Woodstock Square

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8. Woodstock Country Orchard

Editor's Note: Photo taken from the establishment's official social account

Posted by Woodstock Country Orchard on Friday, July 19, 2013

Woodstock Country Orchard is a rural getaway offering the opportunity for participants to pick their very own fresh produce for a small price. They’ve got a variety of different goods, including homegrown garlic, apples, raspberries, local honey and maple syrup. For the city-dweller, this experience is not only affordable but also unforgettable. Plus, it’s family-friendly!

Woodstock Country Orchard

Address: 17015 Garden Valley Rd., 60098 Woodstock, IL

Website: Woodstock Country Orchard

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9. The George Stickney House

The George Stickney House
Source: Photo by Wikimedia Commons user MariahSTI2010 used under CC BY-SA 4.0

The George Stickney House was built by George and his wife, Sylvia, in 1836. The house is said to have had many paranormal occurrences since the original owners’ unorthodox spiritual practices. It’s currently being used as the Bull Valley Police Department but is also a very interesting site to visit for the paranormal enthusiast.

George Stickney House

Address: 1904 S Cherry Valley Rd., 60098 Bull Valley, IL

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10. Woodstock Golf & Games

Editor’s note: Establishment is permanently closed

The Woodstock Golf and Games is a host to all kinds of fun, offering so many fun kids’ activities in Woodstock. There are many different activities to entertain the entire family. There are five batting cages, an arcade with carnival games, 18-hole mini golf, and even go carts which have lit tracks that are open at night!

The best part about Woodstock Golf & Games is that it won’t break the bank. It’s the hot spot for an affordable night on the town with the kids.

Woodstock Golf & Games

Address: 1411 S Eastwood Dr., 60098 Woodstock, IL

Website: Woodstock Golf & Games

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11. Woodstock Opera House

Woodstock Opera House, Woodstock, IL
Source: Photo by user HrAtsuo used under CC0

As one of the oldest operating theaters in the country, the Woodstock Opera House is a big hit. It has even become a highly recognized historic landmark in the Midwest. Singers and performers, plays and musicals from all walks can be found here. It’s especially a favorite of many of the locals. If you’re new to the area and would like to explore a fascinating, cultural location, this is one to check off of the list.

Woodstock Opera House

Address: 121 W Van Buren St., 60098 Woodstock, IL

Website: Woodstock Opera House

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A place of many delights

Woodstock opera house
Source: Photo by Wikimedia Commons user Ginjirotchi used under CC0

Woodstock is not your average small-town getaway. There are numerous places that any visitor must see. Woodstock’s diverse amount of things to do will keep anyone busy because there’s a little bit of something for everyone.

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Frequently asked questions about the best things to do in Woodstock, Illinois

  • What are the best attractions to visit in Woodstock?

    Woodstock, Illinois, is definitely blessed with so many attractions visitors can enjoy including Dufield Pond Conservation Area, Kishwaukee Park, Woodstock Farmer’s Market, Woodstock Square Historic District, and Woodstock Opera House, among others.

  • What are the best activities in Woodstock?

    Woodstock, Illinois, is also known for offering a lot of fun activities in and around town including outdoor recreational activities like hiking and fishing at Dufield Pond Conservation Area, shopping and ding at Woodstock Square Historic District, and watching plays and musicals at Woodstock Opera House.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Lyndi, an up-and-coming writer, college student, and traveler, possesses a profound fascination for exploring the uncharted. She derives immense pleasure from discovering fresh destinations and...Read more

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