Your Ultimate Summer Guide for Kids
Looking for a memorable summer getaway that keeps both the kids and adults smiling? Just an hour northwest of Chicago, Woodstock, Illinois is a charming small town packed with fun, flavor, and family-friendly adventures. From an aquatic center and farmers market art sessions to outdoor movies and live theater, Woodstock offers an unbeatable mix of classic summer experiences and local charm.
Here’s your Ultimate Summer Kids List to help you plan the perfect family day trip—or weekend—in Real Woodstock!
The Woodstock Farmers Market
Start your Tuesday or Saturday morning with a lovely stroll around the Woodstock Square for the beloved summer Market. If you’re visiting on a 1st or 3rd Tuesday morning, don’t miss the Young Artists at the Market program. Kids ages 6 and up can drop in to create fun art projects while parents shop local produce, baked goods, and crafts. A perfect way to keep little hands busy and imaginations flowing.
Splash & Play: Woodstock Water Works
It’s not officially summer without a visit to Woodstock Water Works, the town’s family-friendly aquatic center. With twisting water slides, a lap pool, fun water features, shade umbrellas and a zero-depth entry pool perfect for toddlers, it’s the ideal way to cool down.
Matilda the Musical at the Woodstock Opera House
Plan a stop at the historic Woodstock Opera House for Matilda the Musical Jr., presented by the Woodstock Children’s Summer Theatre. This family-friendly show runs July 11–13, featuring an all-youth cast bringing Roald Dahl’s beloved story to life with music, magic, and heart.
Pizza, Please!
After all that fun, it’s time to grab a slice! Refuel with kid-friendly pizza at one of these local favorites:
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Antioch Pizza – Delicious pizza and sandwiches in a fast casual atmosphere.
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Rosati’s Pizza – Classic Chicago-style pies your kids will love.
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Napoli’s Pizza – Known locally for their thin crust and a welcoming neighborhood vibe.
Play & Discover
Pop into Revelry Toys, a locally owned shop filled with carefully curated toys, puzzles, and books. It’s a great spot to find unique gifts or just spark some imaginative play. If you’re into games, don’t miss GriffoNest Games! This family-friendly shop on the Square offers board games, trading cards, RPGs, and more—plus space to play and explore new favorites together.
For a brain-teasing group activity, try PARADOXsquared Adventure Escape Rooms. These themed escape challenges are perfect for families who love solving puzzles and working as a team.
Join the Where’s Waldo Hunt
Make your downtown adventure even more exciting with the Where’s Waldo Hunt! Search for Waldo figures hidden in 25 participating shops throughout July and collect stamps on your official game passport. Find enough Waldos to earn fun prizes while discovering unique local businesses. It’s a fantastic, family-friendly way to keep kids engaged and explore Woodstock all month long!
Sweet Treats & Snack Breaks
No summer day is complete without snacks! Fuel up between adventures with these tasty treats:
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Pop-a-doodle-Doo for over-the-top milkshakes and gourmet popcorn.
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Rocket Fizz for nostalgic candy, quirky sodas, and fun surprises.
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Millie’s Michoacana for fresh-made ice cream and refreshing paletas with bold flavors.
Movie Magic – Indoors or Out
Beat the heat or wind down with a movie:
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Catch $2 kids’ movies every Wednesday at 10 AM or enjoy $6 movies on Tuesdays at Classic Cinemas Woodstock Theatre.
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On select Thursday evenings, gather for free Movie Nights on the Square, where families watch films outdoors under the stars.
Parks & Playgrounds
Need to burn off some energy? Woodstock’s parks are perfect for play and exploration. Be sure to check out the new Intergenerational and Inclusive Playground at Emricson Park—a colorful, all-abilities space designed for kids of every age. Bonus: Emricson Park also features Disc golf, tennis and pickleball courts, and wooded hiking trails.
McHenry County Fair — July 29 to August 3
If your trip falls at the end of July or early August, don’t miss the McHenry County Fair. Experience carnival rides, farm animals, tractor pulls, live entertainment, and classic fair food—a perfect way to celebrate the season with the whole family.
Plan Your Visit!
📍 Ready to visit? Learn more about lodging, dining, and events at RealWoodstock.com.
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