The City Square Steakhouse

We came here from out of town for our 10 year wedding anniversary. The food, the atmosphere and especially the service that Robyn provided made it a wonderful, romantic evening. Not too often, especially with how COVID has impacted restaurants, do you find the perfect evening but we did at City Square Steakhouse. Management- if you read this, make sure to take care of Robyn and know she deserves much praise! She went above and beyond giving us a memorable evening and we couldn’t be happier! FYI to anyone curious about the desserts- the Butter Cake is AMAZING! We took that back to our bed and breakfast and ate it the next day!

What a superb place for a date night. Made reservations for 4:30 and got in right away. Place felt fancy without being to uptight. Hostess and waiter were both very polite, courteous, and pleasant. Food arrived in a timely manner and just how we asked. Wasn't horribly overpriced and the salads were excellent as well. Will be returning.

We were celebrating my husband's birthday and The City Square Steakhouse did not disappoint. It was our first visit. After using Open Table to make an online reservation, I called to inquire about dress code, expectations, the ability to work around allergies, and wanting a socially distanced outdoor table on the patio. Isaiah was super helpful to answer all my questions, including checking with the kitchen regarding allergy friendly options. He also gave a heads-up for parking. Woosterfest was taking place during our visit and numerous roads were blocked off. Once we arrived, we met Isaiah face to face, and were introduced to our AMAZING server, Robin. She was polite, friendly, courteous, knowledgeable about the menu, and great at making conversation. We felt like we had known her for a lengthy time. Kirk made his rounds to check on us and was welcoming too. We witnessed another server, Mason, taking good care of his tables. The outdoor fire pit added great atmosphere all while listening to live music from Woosterfest up the street. We will definitely be back!

First off, the decor and setting are both absolutely gorgeous. What a beautiful place to eat dinner! We sat in a booth. My wife and I had our six month old with us (perks of being parents, dates include the little ones.) I was expecting higher prices just by the other bit I read before arriving. We had called ahead confirming that the dining room was open and their hours. It wasn't super quiet even though the setting felt like it should be. The random outcries of our little one weren't too outlandish despite the cringes of dad (me) every time it happened. Anyway, after sticker shock subsided, we ordered - off the bottom of the list. I ordered a pork chop and my wife ordered the salmon. I was informed shortly after ordering that they were now out of pork chops (she knew they were low but did try to get the order in time, oh well - typical of my luck.) So, I got a sirloin instead. I must say, the sirloin was quite unimpressive. For the price and everything, I really had high expectations for this steak and it fell considerably short. There was little flavor at all. I ordered medium and it was well. Some of you may say - well, it's a sirloin so... That was taken into consideration. I feel Texas Roadhouse actually makes better steaks than what that was. In fact, my next trip to the Roadhouse will include a cheap sirloin just to compare. On a scale from 1-10, I would say this steak landed solidly around a 4. I had sweet potato fries on the side and let tell you, friend, those did not disappoint. They were absolutely delicious and would recommend this locale strictly based on the fries. 🤤🤷 Sweet potato fries landed around a 9/10. Side note - apparently the honey mustard that I utilized to help drown the steak (if you require a sauce with your steak, it isn't a good steak) was actually supposed to be used for the fries. Who knew 🤷. My wife was satisfied with the salmon and rice. It was almost undercooked, but was still satisfactory. All in all, I would love for a second chance at this place. I feel it has so much potential and we barely scratched the surface despite maybe getting a little bit of the poor side of the food. The service was okay. The food came quick and the staff was courteous. Our waitress could have been a lot quicker but she was nice and professional so I really can't complain ( despite having a very impatient 6 month old.) I truly think this place has a lot of potential hence the 5 star rating.

My son surprised me and treated me to dinner. This place is beautifully decorated. We were seated in the room with the fireplace. I love to see that this beautiful historic building was preserved. Our waiter, Mason, was very helpful. We enjoyed our dinner very much. The food was very fresh and delicious!

Made reservations for my birthday celebration based on their high-rating for a steakhouse. Service was impeccable, restaurant was cold and I needed to keep my coat on my shoulders. Salad was fresh and dressing good, but for a $57 Delmonico steak, I was sadly disappointed. Not to mention the extra charge for Oscar style. Steak was cooked per order, but it was a very poor cut of beef. Tough, chewy. An over $200 bill for the two of us left the us very disappointed. The manager checked in when we are on way out the door. We shared our honest review. He seemed genuinely concerned and wanted to do something to make up for the experience. I gave him my business card and we shall see if he reaches out. Overall, on the food front - way less quality than expected. It was a let-down.

This place is incredible! The service is top-notch and the food is amazing. Our server, Michael, was awesome and very engaging. I had the bourbon sampler and Michael recommended a fabulous bourbon to try (Angel's Envy Rye), which is now my new favorite. Not one, but two managers came by to make sure everything was good with our food. One of the managers had a conversation with us about bourbon and I was impressed with her knowledge of the subject. Another manager brought me what turned out to be the last shot in the bottle of Angel's Envy Rye and offered it at no cost. I, of course, gladly said yes. My wife and I really enjoyed our meals here and will certainly be back. Michael, if I find the Angel's Envy Rye I'll buy two bottles and bring you one. Thanks for a great dining experience!