Squire on the Square

06/05/2026

☀️🍹 Patio season is in full swing, and there’s no better place to relax than Squire on the Square!
Before, during, or after the Woodstock Food Truck Festival, join us tomorrow on the patio for your favorite drinks, great company, and a perfect summer evening in downtown Woodstock.

🌮 Woodstock Food Truck Festival
📅 Saturday, June 6, 2026
⏰ 4:00 PM – 9:00 PM
📍 Woodstock Square, Woodstock, IL
🎟️ Free Entry

With 30+ food trucks, family-friendly fun, and a beautiful night on the Square, it's the perfect excuse to spend the evening downtown.

Grab a Mai Tai, find a seat on the patio, and enjoy all the excitement Woodstock has to offer! 🍹🌞

06/02/2026

🐾☀️ PAWS ON THE PATIO IS HERE! ☀️🐾
Join us at Squire on the Square for a tail-wagging good time on the patio! Bring your furry best friend, enjoy a special treat made just for pups, and help support a great cause.

❤️ A portion of proceeds will benefit Helping Paws Woodstock, IL
📅 Second Thursday of the Month June - October
🕔 5:00 PM – 7:00 PM
📍 Squire on the Square | Woodstock

Mark your calendars now:
🐶 June 11
🐶 July 9
🐶 August 13
🐶 September 10
🐶 October 8

Don't miss our Sniff & Snack Dog Special featuring a rice bowl with chicken or beef and a pup cup for just $10!
Tag your dog-loving friends and let us know which pup will be joining us on the patio this summer! 🐾🍦🍖

06/02/2026

Congratulations, Sophia Klein! 👑✨
The entire Squire on the Square family is incredibly proud of you! Join us in celebrating Sophia's amazing accomplishments as Miss Woodstock 2026 First Runner-Up and Talent Award Winner.

Your hard work, grace, dedication, and talent have truly shined throughout this journey. We are honored to have you represent Squire on the Square and can't wait to see all the wonderful things ahead for you.

Please help us congratulate Sophia on this outstanding achievement! 🎉❤️

06/01/2026

This weeks live music lineup

06/01/2026

Bucket list for this summer:
☑️ Sit on the patio
☑️ Order a bucket
☑️ Stay for “just one more”

Now pouring our NEW patio-perfect deal:
🍹 5 for $25 🍹
Tuesday–Sunday

05/31/2026

🌿✨ June starts here, and so are some incredible new specials at Squire on the Square! ✨🌿

We're kicking off the month with flavors you won't want to miss, from our creamy Baked Goat Cheese Appetizer and fresh Goat Cheese Salad to the hearty Steak Sandwich, flavorful Zucchini Pasta, and indulgent Short Rib Gnocchi Bowl.

Whether you're joining us for lunch, dinner, or a night out on the Square, there's something delicious waiting for you this June.

👇 Tell us in the comments: Which June Special are you trying first?
Tag a friend you'd bring with you and make plans to stop by this month!

05/29/2026

Looking for an easy way to meet more local business owners and professionals?

Bites & Business is designed to keep networking simple and welcoming. Grab a seat, order lunch, and enjoy natural conversations with others in the local business community.

Whether you’re brand new to the Chamber, a longtime member, or just looking to expand your network, this is a great midday opportunity to connect without the pressure of a formal program.

Thursday, June 18
12:00–1:30 PM
Squire on the Square

Register here:
https://business.woodstockilchamber.com/events/details/bites-business-at-squire-on-the-square-19154



Woodstock Area Chamber of Commerce & Industry
Your connection to local business & community.
🌐 www.woodstockilchamber.com
📞 815-338-2436

05/29/2026

05/29/2026

Patio season is officially here ☀️🍹
It’s going to be a beautiful weekend! Join us on the patio for cold drinks, great food, and even better company!! 🍻

Summer starts here, see you on the patio!

05/27/2026

The king of steaks.
A perfectly cooked T-Bone, packed with flavor and made to satisfy.

No shortcuts. Just great steak.