Visit Woodstock, Illinois! Small-town charm in the northwest suburbs of Chicago. Totally road trip worthy. Farmer’s Market Tuesdays and Saturdays. Shop the Woodstock Square or venture out further to visit a local farm. Living here every day is a drea...
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This is a medieval-inspired restaurant in the Old Courthouse building on the historic Woodstock Square. Fun to go there late nights for Cheesecake Factory cheesecake and drinks or to sit on the patio and watch people going to the Farmer’s Market on S...
Squire on the Square
Small town theater vibes outfitted with luxury seating. Check out the cool mural a with a nod to classic movies one block north of the theater.
Classic Cinemas Woodstock XQ
Pick your own strawberries, sunflowers, apples (depending on the season) farm that sells produce and bakery items onsite. A nice drive in the country.
Stade’s Farm & Market
Nursery at the edge of town. They really know how to put baskets together.
Kolze's Corner Gardens
Long-standing customer favorite in Rockford, IL opened a Woodstock location a couple years ago. Affordable and their cream-filled long johns are second to none!
By The Dozen Bakery-Woodstock, IL
Stop by to satisfy your sweet tooth. Fun for kids and kids at heart. Right on the Woodstock Square.
Rocket Fizz Woodstock
You’ll feel right at home. Nestled in our historic neighborhoods. A nice walk to the Woodstock Square.
Cherry Tree Inn B&B | Groundhog Day House | Woodstock, IL
Buy your next album and check out the art vending machine.
The Records Department
Stroll the Square at night and catch some live music on the street in front of Winestock.
Winestock Market & Lounge
Chef’s kiss. My favorite pizza in Woodstock. The owners do a lot to support the community. Good hot and fresh the night of or cold the next morning (if there is any left over).
Napoli Pizza Place
Good way for the littles to burn energy. They will have plenty of company here.
Woodstock Water Works
Take a picnic and sit by the lake, watch a little league game or score points of your own on the tennis/pickleball courts. Plenty of walking trails and an intergenerational playground.
Emricson Park
I know someone who won’t dine anywhere else when they visit Woodstock. The Italian beef is that good. So is everything else. In a word-fresh.
Beef Village
U pick flowers. Say no more. 🌸
Dented Gate Flower Farm
A couple blocks from the Square. Break-worthy spot to scroll on social media (without having to buy anything) or get some ideas for your next read.
Woodstock Public Library
My favorite coffee place in Woodstock. Delicious drinks, fresh made chocolate and a speakeasy at night. Here you’ll find a mix of visitors, business meetings and Moms making a pit stop to fuel their day out with the kids.
Ethereal
Something for everyone here at fair prices. My sister bought a piece that now serves as a bar in the dining room.
Black Oak Home & Haven Co.
A local teacher opened this store. Friendly competitions happening all of the time. Looking for a new game? They have you covered.
GriffoNest Games
One of many conservation areas in Woodstock. Hard to pick only one but you’ll enjoy it.
Pleasant Valley Conservation Area
I never miss the Christmas tree display around the holidays. Check out a top-notch performance. Something always going on at one of the top performing arts centers in the Midwest.