Inside the City Square Steakhouse

Last night we wanted to go out but were tired of the same old places in town. (You know the drill, you ask “Where do you want to eat?” and Dustin replies “I don’t know. Nothing sounds good. Where do YOU want to eat?”) We love Cheddars and Olive Garden but wanted a smaller restaurant in an area we hadn’t been before. I jumped online and began looking up places in Wooster, Ohio. I had seen signs for a place called The Barn and had remembered a friend say that there were a lot of shops in the area. Wooster is about thirty minutes from our house and is a college town. We never really hear of people hanging out in Wooster, but I thought there may be some gems to discover!  I was shocked at the amount of restaurants serving up quality food that resembled Chicago fare. I mentioned a few places to Dustin and we headed East.

Wooster is beautiful. There is so much architecture and lots of restored places. We found some free parking and felt like we were downtown Chicago in Lakeview or near Lincoln Park. Tons of other couples dressed up were walking around arm in arm.

We began out evening at The City Square Steakhouse. As soon as we walked in we gave each other “the look” which said “this place is legit!” Beautiful exposed brick walls were highlighted with spotlights and photography. High back booths lined the corner and tables with white cloths filled the floor. When you walk in, you walk into the bar area which is stunning as well. Situated in an old building, the Steakhouse has different rooms. Behind the bar area is a room with a fireplace and library shelves. Further into the intimate space is a patio and dining space opening up to it. Our host led us to a quaint table right near the window for two. We grabbed the menus and dug in!



The menu at the City Square Steakhouse is…pricey. I had looked the place up before and knew that burgers were about $10-12. When we sat down in the dining room we weren’t brought a menu with them. Instead, the cheapest entree was about $20. Cringing I asked if they offered burgers in the dining area or if we needed to go to the bar. Our waiter didn’t hesitate and brought us the burger menu. We were on our way to delicious (more affordable) food. The regular menu was so delicious looking that we ordered an appetizer. The Housemade Chips with Roasted Red Pepper Blue Cheese Dip was $6.75. When it came to the table, we smiled even bigger! This is an appetizer worth splurging on! The chips were crispy and warm. Dipping them into the cheese just took it over the top. We were also offered fresh bread with butter.


Luxe dining room at the steakhouse


House chips!

Our meals came quickly. I got the Mushroom Swiss Burger with garlic mashed potatoes ($11.50) and Dustin went for the Blue Cheese Burger with fries ($10.75). The burgers were done to order and were extra big. The Mushroom Burger came with mushrooms, swiss cheese and rosemary mustard. The Blue Cheese Burger came with grilled onions, blue cheese and mayonnaise. We only ate 1/2 and had them package the rest up to go. Flavors upon flavors and attention to detail impressed our socks off. Our waiter was super friendly and classy without being too intimidating. Although we dined on burgers in a restaurant that served $60 steaks we felt our business and presence was appreciated. This made us want to come back! Although we’re not big steak people, my dad and sister are and would probably order a more expensive entree. We can’t wait to bring them and share this special discovery!




Imperial Gatsby

After dining at the steakhouse, we went to find a wine bar I found online. It was sadly closed so we walked around and headed to Oak Grove Eatery. This eatery just re-opened in the Spring of 2014! They’re known for their freshly made food with a focus on local ingredients. Their coffee is made by their sister company, Oak Grove Coffee Co. and it’s organic and fair trade. Open for breakfast, lunch and dinner, you really can’t go wrong with this place! The eatery was packed around 7pm so we sat at the bar. The interior is the perfect blend of modern and rustic. Ceramic pitchers refill your water and you can see into the kitchen in the back. High top tables, low tables and booths create different seating options and everyone from older couples to young families were eating. Our bartender was hip, friendly and fun. She didn’t hover over us but gave us plenty of attention and suggestions. We began ordering a port wine and a cocktail. Later, we ended up adding a dessert. I had the Emilio Lustau Deluxe Cream Sherry dessert wine. Wow! Did it pack a flavor punch. It was rich and had nutty undertones. Dustin ordered the Imperial Gatsby. This drink had a sugar cube and an orange peel. I really can’t recall what else was in it. It was good but not as sweet as I would like.


Bar at the City Square Steakhouse

After drinks we ordered a sundae with homemade chocolate fudge, a brownie and coffee. It was delicious. It went perfectly with the port wine. I’m not a huge fan of ice cream but this was perfectly blended and creamy. After the $25 bill for dessert and drinks, we laughed but enjoyed our stay visiting and telling stories as it rained lightly outside.


Inside Oak Grove

After the Oak Grove Eatery we walked around downtown Wooster. We discovered a cool old bookstore (I looked it up and it’s called the Wooster Book Company) that had all types of old and rare books. It was open until 9:00pm so we wandered the shelves and explored the upstairs. Although it was a great bookstore, I gawked at the price of books ($5-9) and didn’t look for any to take home. Other things we saw were: a coffee shop, art store, bakery and other restaurants.


Across the street from City Square Steakhouse, Oak Grove Eatery

We look forward to visiting again and checking out Broken Rocks Cafe & Bakery, Muddy Waters Cafe & Grill, First Amendment Public House, Spoon Market, and Tulipan Hungarian Pastry & Coffee Shop.

We splurged a little bit. Here’s the breakdown.

Appetizer, 2 burgers & water at The City Square Steakhouse $30 ($36 with tip)

1 Glass of wine, 1 cocktail & shared dessert at Oak Grove Eatery $25 ($30 with tip)

Total: $66

Travel/date night tip: Get quality H20 at dinner and skip dessert. This way you can spread the night out and enjoy two separate places. You could also make this date cheaper by skipping the appetizer altogether and just ordering 2 burgers. We also tend to order an entree and appetizer and share both instead of 2 entrees. If you want to do drinks/dessert cheaper buy a cake mix and bottle of wine and have a “baking night”