Squire on the Square

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.

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.

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.

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.

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.