Urban on the Square
Winterset, Iowa, USA
Discover Urban on the Square, a trendy restaurant in Winterset, IA. Enjoy fast service, great cocktails, and a diverse menu from $10–20. Open Mon-Sat.
69 E Jefferson St, Winterset, IA 50273, United States
Urban on the Square
Winterset, Iowa, USA
Overview
Urban on the Square is a trendy restaurant located at 69 E Jefferson St in Winterset, IA, offering a refined yet casual dining experience. With a highly praised menu featuring comfort food and healthy options, this spot is known for its fast service and inviting atmosphere, perfect for tourists and locals alike.
The venue features a great selection of beer, cocktails, spirits, and wine, alongside thoughtfully prepared dishes such as the Chicken Deburgo, Lemon and Garlic Shrimp pasta, and tempting desserts like Crème Brulé. Guests can choose between takeaway or dine-in service within a cosy, urban setting that welcomes both groups and solo diners.
Gallery
Real shots of the food, atmosphere, and signature dishes at this location.
Local favorites
Urban on the Square attracts guests seeking a casual yet trendy dining experience with a focus on quality and comfort in the heart of Winterset.
Quick and attentive service makes it an ideal spot for lunch or a casual dinner without a long wait.
A wide variety of cocktails, beers, and spirits complement the menu perfectly for a relaxing meal or night out.
Popular dishes like Chicken and Brussels, Carrot cake, and Creme Brulee earn top marks from diners and critics alike.
The casual, cozy, and trendy setting fits groups, tourists, and solo diners looking for comfort food or healthy options.
Located on Winterset’s square, with free parking, wheelchair accessibility, and table service for comfort and ease.
Offers flexible dining options including takeaway, perfect for busy days or enjoying on the go.
High chairs and a welcoming environment make it easy to bring children along for lunch or dinner.
Experience
Discover the best moments to visit Urban on the Square for a flavorful meal and vibrant atmosphere.
Exceptional food quality matches a friendly ambiance, making it a top choice for both casual lunches and relaxed dinners in Winterset’s historic square. — FoodPlacee editorial note
Ideal for a midday meal, the diverse menu includes fresh salads and hearty entrees perfectly suited to recharge during a busy day.
With spacious seating and friendly service, it's a great spot for groups to enjoy an urban yet cozy dinner together.
For those seeking quality comfort food at home or work, the takeaway option offers a convenient way to experience the flavors of the menu.
After a day around town, unwind with expertly crafted cocktails and a great beer selection at the on-site bar.
A welcoming atmosphere that’s perfect for solo diners looking for a casual yet high-quality meal.
Advance reservations ensure a smooth and relaxed dining experience, especially for busy lunch or dinner hours.
Guest sentiment
A snapshot of what local diners frequently mention about this location.
"The salmon BLT and sweet potato fries were delicious, the fries were the best I've had. Beautiful old courthouse across the street."
"Had a wonderful lunch here. Great food selection and friendly service. What a gem!"
"This quaint little restaurant on the square in Winterset was a great find to start our short trip to Iowa. My steak sandwich was delicious! My husband really enjoyed his Reuben with side of French onion soup. The desserts I. The case looked very tempting but we were too stuffed to try them."
"What a lovely addition to Winterset. We didn't make reservations, but we were able to sit at the bar. Heather was very attentive and made conversation. I had the blueberry bash martini it was really good. We also had the crab ragoon dip, yum is all I can say. For our meals, we had salmon with lemon dill and lemon garlic green beans and chicken with Brussels & rice. All in all I would say it was a great experience and the food was really good not too much but not too little. Oh, and I can't forget the carrot cake & chocolate cupcake!"
"Stopped in on a trip through Winterset on our way to Des Moines. Urban on the Square was right off the main road through town and lives up to its name! The restaurant was right in the square across from the County Courthouse. We were able to secure curb parking right outside and were met with an urban but inviting interior. I believe our server was new/in training but that didn’t dampen the great service we received while we indulged in appetizers, entrees and even desserts. Their serving sizes were oversized, considering we were there for lunch. Their desserts especially we could have easily split one among the four of us present. Overall, the experience was great and we would definitely dine there again if we’re in the area!"
"This was one of the tastiest lunches I've ever had! The Madison County Chamber of Commerce recommended we visit here on a daytrip to the area. Evidently, the restaurant owners operate five restaurants in the area, including Urban Taproom and Grille and The Urban Grill. We started with the French Onion Bruschetta, which was very tasty and unique. For our meals, we had the Shrimp Tacos, Spaghetti & Meatballs, and the Steak Deburgo. Our favorite was definitely the Steak Deburgo, which was incredibly tender with an amazing flavor. We finished with the Creme Brule and something like a chocolate mousse cake, which was not on the menu. They definitely hit the spot. The whole meal was fantastic! The service was exceptional. I think our server's name was Ashley and she was super friendly and helped us navigate the menu. Our son insisted on the spaghetti, but we otherwise pretty much let her choose our foods. She did not disappoint! We will definitely stop in here for lunch or dinner the next time we're in town. It will be hard to not order that Steak Deburgo, though!!!"
"My husband and I have been looking forward to trying out Urban on the Square for awhile now, and whoa, were we impressed. Everything was so flavorful, staff were all very friendly, atmosphere was quaint and cozy… I highly recommend it. Make sure you try the French onion soup and the chicken and Brussels!"
"We had a great experience! The food was very well done- the Inside out Crab Rangoon was a favorite, the Steak Deburgo was nicely done, the chicken in the chicken and Brussels was fork tender and the risotto paired perfectly with the hollandaise. We will be back. So nice to have a good date-night spot in Winterset!"
Visit info
Weekly hours below — always confirm with the business before holidays or special events.
| Monday | 11:00 AM - 03:00 PM |
| Tuesday | 11:00 AM - 03:00 PM |
| Wednesday | 11:00 AM - 03:00 PM |
| Thursday | 11:00 AM - 03:00 PM |
| Friday | 11:00 AM - 03:00 PM |
| Saturday | 11:00 AM - 03:00 PM |
| Sunday | Closed |
Serving lunch and dinner from 11:00 AM to 3:00 PM Monday through Saturday, this spot is perfect for midday or early evening meals.
On the map
Find your way to Urban on the Square in Iowa .
Questions answered
Find answers to common questions about dining at Urban on the Square in Winterset, IA. This FAQ covers hours, menu options, accessibility, and more to help plan your visit.
For owners
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Menus, prices, hours, services, and availability may change. Please contact the food place directly before visiting or ordering.