Savor the Last Days of Summer

Escape Real Life. Make Summer Last!



August has a funny way of making us want to do it all! One more concert. One more stroll through the Farmers Market. One more funnel cake at the fair. One more dinner on the patio. Luckily, Woodstock makes it easy to check every box before summer says goodbye!

Celebrate National Farmers Market Week

Fresh Picks and Square Strolls

National Farmers Market Week is August 2-8


August is when the Woodstock Farmers Market truly shines! Sweet corn, juicy tomatoes, crisp cucumbers, colorful peppers, fresh-cut flowers, homemade treats, and artisan goods fill the Square as the season reaches its peak. With markets every Tuesday and Saturday from 8 AM - 1 PM, each visit brings fresh flavors, new finds, and another reason to spend the morning in Woodstock.

August Highlights

Meet Me at the Midway

August 4-9


Nothing says summer quite like a day at the McHenry County Fair! From carnival rides and livestock exhibits to favorite fair foods and live entertainment, this is one of the biggest traditions of the summer! Catch the power of the Draft Horse Pulls, cheer on contestants during the Pizza and Corn Eating Contests and don't miss Carnival Ride Wristband Day or the Round Bale Rumble for unlimited thrills! Fun for all ages!


Cue the Music

Fridays | 7-9 PM


Warm summer nights, free live music, and the Historic Square. The August Summer Concert Series is one of the best ways to experience Woodstock. Bring a lawn chair, your dancing shoes, and enjoy the concerts put on by regional talent!


August 7

The Boat Drunks


August 14

The Blooze Brothers


August 21

Chicago Latin Band

Chrome Sweet Chrome

August 15


The Hot August Night Benefit Car Show rolls into the Historic Square with polished classics, vintage trucks, custom builds, and motorcycles. Enjoy live music, local vendors, great food, and incredible vehicles during one of Woodstock's favorite summer traditions.


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Local Flavor Worth Savoring

Oak & Alchemy

11671 Catalpa Lane, Woodstock


Built around the art of cooking with fire, Oak & Alchemy is serving up slow-smoked barbecue, authentic wood-fired pizza, handcrafted cocktails, and a warm, inviting atmosphere. Whether you're ending the day after exploring Woodstock or meeting friends for dinner, it's a flavorful addition to the city's growing dining scene that's worth experiencing!

Things to Celebrate This Month

Book Lovers Day

August 9


Spend Book Lovers Day exploring Woodstock's literary side! Browse the latest bestsellers at Read Between The Lynes, hunt for hidden treasures at The Green Spot Used Books, and discover collectible finds at Carpetbagger Books.


Looking for more inspiration?

Check out our Book Lover's Guide to Woodstock, IL for the perfect literary itinerary.

National Thrift Shop Day

August 17


Every great thrift find starts with a little curiosity. Explore Woodstock's collection of vintage boutiques, antique shops, and thrift stores. From timeless treasures and unique home décor to sustainable fashion and unexpected finds, every stop offers something different.


Looking for the best places to start?

Check out our Discovering the Charm of Thrift and Vintage Shopping in Woodstock, Illinois blog.

Upcoming Events at the Opera House

Circus of Bubbles LIVE

September 12



Learn More >>

Comedy Dance Chicago

September 19



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Late Night Catechism

September 27


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August Events in Woodstock

Afternoon Tea: Magnifique Journey

Through August 30


Woodstock Farmers Market Tuesdays & Saturdays


Absurd Art Social Club

August 1



A Night Out: Sip & Carve

August 1


Outdoor Dog Yoga

August 1


Smokin' In Woodstock August 1


Shakespeare Players: A Bit O' The Bard

August 1


Halfway to Groundhog Day

August 2



Live Inspired: Ignite Your Passions

August 2


Board Game Night

August 6, 13, 20, 27


Jam Making Workshop

August 6


Free Outdoor Movies

August 6 & 8

Tacos and Test Rides

August 8


Woodstock Art in the Square

August 9 & 30



Sundays on the Square with OffSquare Music

August 9 & 30

Bookstore Romance Day

August 15

3rd Annual Truck'n Food Show

August 28


Brass in the Barnyard

August 28



Original Open Mic Night

August 28

Cass Street Music

August 29


Save the Date

Mexican Independence Day

September 13, 2026

Autumn Art Tour

September 12, 2026

Woodstock Art Fair on the Square October 3 & 4, 2026



Autumn Drive

October 16 - 18, 2026

Annual Lighting of the Square November 27, 2026



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