Checkerboard Restaurant

Pizza Restaurant
108 E Monroe St, Pleasantville, IA 50225, United States
(544 Reviews)

Description

Checkerboard Restaurant is located at 108 E Monroe St, Pleasantville, IA 50225, United States. This Pizza Restaurant has received 544 user reviews. It offers a total menu featuring dishes such as Homemade Onion Rings, Large Italian Sausage Pizza, Tenderloin Sandwich, and Italian Sausage Sandwich.

Categories

Pizza restaurant

Amenities

  • Takeout
  • Dine-in
  • Delivery
  • Fast service
  • Serves local specialty
  • Solo dining
  • Wheelchair accessible entrance
  • Wheelchair accessible parking lot
  • Wheelchair accessible restroom
  • Wheelchair accessible seating
  • Alcohol
  • Beer
  • Coffee
  • Comfort food
  • Salad bar
  • Wine
  • Dessert
  • Table service
  • Restroom
  • Cozy
  • Historic
  • Family-friendly
  • Accepts reservations
  • Checks
  • Credit cards
  • Debit cards
  • NFC mobile payments
  • Good for kids
  • High chairs
  • Kids' menu
  • Free parking lot
  • Free street parking
  • Parking

Checkerboard Restaurant Photos

Reviews (544)

5 Superb Reviews Out of 544 Reviews
Amazing
371
Great
103
Okay
40
Not Great
19
Terrible
11
  • Duane Mann
    Jan 30, 2026 - 2:17 am

    Gotta love the place. Decorated throughout with antiques from early settlers and Old West. Waitresses had cowboy hats and six guns. Had taco pizza and bacon cheeseburger pizza. Both very good. Menu had, sandwiches, appetizers, dinners, and salads as well. Service was fast and friendly. Well worth the stop.

  • Art Olson
    Jan 06, 2026 - 4:49 am

    A True Gem! Awesome food and Great service! Portions are generous and prices are very fair! Food tastes just like homemade. If you haven't already tried them out, I highly suggest you do! Yum!!

  • John Crippen
    Jan 02, 2026 - 4:22 pm

    When we arrived we were greeted by the best hostess this side of the Mississippi. Alyssa was very friendly and made sure we got the table that made us most comfortable. The pizza and onion rings were the right choice. I love me some pizza.

  • Pmitchell@gmail.com Mitchell
    Nov 30, 2025 - 2:22 am

    Great employees and awesome pizza. Blueberry wine is great. The waitress is Kristen is great.

  • Gena Schneider
    Nov 28, 2025 - 2:55 pm

    This is a restaurant I grew up with. They have amazing onion rings, and I recommend the taco pizza. They are about to celebrate 50 years under the same owner and she has been through it. The atmosphere is rustic and has a lot of interesting things to look at but is not really my style, but I look past it because the food is a kind of comfort food for me.

  • Linda Shelton
    Nov 27, 2025 - 6:01 am

    Was there with a large group of family members. Others raved about the onion rings. Everyone loved the pizza—we had several different toppings. The service was attentive without being overly so.

  • Scotty Ryland
    Nov 21, 2025 - 1:20 am

    This place is amazing. This restaurants is a little slice of history. It tells a story of the owners life. It was amazing meeting Karen, the owner! She showed me and my wife around telling g us stories of how the restaurant came to be. The staff is amazing and the onion rings are perfect!! Will definitely come back to Iowa just for this wonderful find.

  • Brooke G
    Nov 19, 2025 - 8:23 am

    While our son was hunting deer for the season… We decided to check out a restaurant we have been hearing amazing things about but hadn’t tried yet. DELICIOUS!!! So much to say about this place! The owner, Karen, stopped at our table…such a sweet lady! Nearly 48 years in business!! She mentioned her husband did all of the remodel and she takes pride in their unique decor! Also gave us a plate of their amazing onion rings! They are a MUST! Pizza crust is homemade and a nice crisp to it! It was PERFECT! Our sweetheart waitress, Bella, was so patient and helpful! HIGHLY recommend! We will be back!

Add Your Review

Your email address will not be published.

Subscribe to Newsletter!

Subscribe to get latest updates and information.

Suggest Edit