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Experience a modern take on a beloved local landmark at Squire on the Square, located in Woodstock’s historic Old Courthouse. This inviting restaurant serves elevated lunch and dinner menus featuring both classic favorites and creative new dishes. Guests can enjoy Village Squire staples like saganaki, gyros, and prime rib alongside fresh creations such as Ahi tuna wontons and smoked brisket. With a full bar, cozy dining room, and spacious patio overlooking the Square, Squire on the Square is the perfect place to gather, dine, and celebrate in the heart of Woodstock.
Address and Contact Information
Address: 101 N Johnson St, Woodstock, IL 60098
Phone: (779) 247-2089
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Home – Squire on the Square – Restaurant in IL
Squire on the Square in Woodstock, IL. Check out our location and hours, and latest menu with photos and reviews.
Squire on the Square | Woodstock IL – Facebook
Join us at Squire on the Square as we kick off the luckiest season of the year in true Irish style!✨ We’re bringing the festive vibes, the green drinks, and …
Squire on the Square | Enjoy Illinois
Nestled in the heart of the historic Woodstock Square, Squire on the Square brings a unique blend of American and Greek cuisine to the timeless charm of the …
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Reviews
Kay Chalad
We visited Squire on the Square and ordered the giant pretzels, schnitzel, and the Parmesan-crusted cod. The pretzels and schnitzel were great, but the fish came out undercooked. The staff handled it very well—they were quick to make it right, and I decided to switch to the pot roast instead. I’m so glad I did! Their pot roast is absolutely amazing, tender, and full of flavor. I highly recommend it to anyone visiting Woodstock, IL. The great service and delicious food definitely made our visit worthwhile.
… moreLaura Reichert
If you’re a Groundhog Day fan, Squire on the Square is an absolute must. A portion of the movie was actually filmed in this establishment, and getting to eat and drink in the very place where that “Drink to World Peace” moment happened was such a surreal, nostalgic highlight of our trip. It honestly felt like stepping right into the movie.
The food was really good, and the specialty drinks were excellent, creative, delicious, and totally worth ordering (especially if you’re making a whole Groundhog Day weekend out of it). The atmosphere was upbeat and fun, and it’s beautiful inside , warm, cozy, and full of character.
Even without the movie connection, I’d recommend it for a meal or cocktails. But with the Groundhog Day history? It makes it that much more special.
… moreThe food was really good, and the specialty drinks were excellent, creative, delicious, and totally worth ordering (especially if you’re making a whole Groundhog Day weekend out of it). The atmosphere was upbeat and fun, and it’s beautiful inside , warm, cozy, and full of character.
Even without the movie connection, I’d recommend it for a meal or cocktails. But with the Groundhog Day history? It makes it that much more special.
Arnold Grahl
Unique atmosphere. Creative holiday decorations. Staff very friendly and you get a bowl of popcorn while pondering your order. Brisket sandwich a bit too chewy but sauce fine. Rueben had right amount of sauerkraut and dressing came on marbled rye. Generous amount of fries which were a bit soggy and lukewarm. Great scenic location right of historic square.
… moreMatthew Zamudio
Was surprised to see this was a Squire! Great as always for food, beer, and atmosphere. I love being able to come to Woodstock and hang out here, knowing I will have a great dining experience. 10/10 will be back many times.
… moreDavid Margolis
Great food and outstanding service whenever we visit the Squire.
Tonight was Halloween and it was a fun night with The staff dressed in costume along with many of the customers.
Paul the Bartender and William the Manager are exceptional.
We look forward to our next visit.
… moreTonight was Halloween and it was a fun night with The staff dressed in costume along with many of the customers.
Paul the Bartender and William the Manager are exceptional.
We look forward to our next visit.
Curtis Park
Squire on Square is amazing. I appreciate the staffs and managers kindness to me even though I have autism and their food is amazing and really good. Owner Bob and manager Sophia is very nice. The restaurant is in good condition. Awesome boom boom shrimp tacos and the rice that comes with it is the best rice I’ve ever had. Must come back. 10/10.
… moreJordan “Pacific NorthWest Yetti.” Pawley
This was fantastic, we just happened to see it open after checking out the decorations in the square. It was honestly stupidly good. The brisket mac b cheese was amazing, the ahai apps were really good,….Well everything we had was good. The inside decorations also just hit the spot. Would 100 percent recomend, and if i was even remotly local i would go here a lot. And dprobably be 500ibs.
… moreKeyuna Web
I had the best grilled cheese sandwich there I’ve had in a loong time and I loved how the drinks were served in mason jars. It was very charming atmosphere and the staff were so hospitable as a traveling tourist ❤️
… moreLovena Hunter
Absolutely love Squire, and having this addition to Woodstock is a great compliment to this town. The food is always amazing, and the service was stellar. Our waitress was so fun and kept us laughing through each interaction. We loved her. Rum Barrels are my favorite. We really enjoyed everything about our visit. I wish them great success at this location. I intend to visit again soon!!
… moreAshley Chrusniak
Went for dinner Friday night they were busy but got us in right away. We order a Mai Tai and bang bang shrimp to start. The drinks were good. The shrimp was okay not my favorite it was breaded shrimp in bang bang sauce and they were a little soggy. I’ll definitely try something different next time. For our main meal I had to do the prime rib and the husband went with fish a chips. My prime rib was delicious. I opted for the 11 oz which was plenty for me it was tender and melted in my mouth. My husband wished he got one instead of his meal he thought his was just okay. He said the breading on his fish was to salty for his liking. I enjoyed his meal the next day and thought the fish and potato was good. We decided to get dessert I got the carrot cake and he did the cookie skillet. I also had a espresso martini for dessert. All 3 items were wonderful the cake was moist and flavorful. The cookie was so good with ice cream. And the martini was the perfect way to end the dinner. The service was great and attentive but not over the top.
… more