There’s the coffee shop that started right here before growing into a familiar name across Iowa, the local bar and grill that took home the state’s Best Burger title, and a longtime family restaurant where the onion rings have become a local favorite.
Whether you’re looking for a place to grab coffee, stopping for lunch or just looking for an excuse to take the scenic route through Pleasantville, here are three spots worth knowing about.
You may have stopped at a Smokey Row Coffee somewhere else in Iowa, but did you know the original is right here in Pleasantville?
The story behind the name is pretty fitting for a small Iowa town that has seen its share of rebuilding. After several fires in Pleasantville’s downtown in the late 1800s and early 1900s, the row of buildings along Main Street became known as “Smokey Row.” When the coffeehouse opened in Pleasantville, the name became part of a new chapter for the same stretch of downtown.
What started here eventually grew into the Smokey Row locations people know throughout Iowa, but the original is still serving the Pleasantville community today. Stop in for coffee, breakfast or a baked good, and you’re getting more than a caffeine fix. You’re sitting in a piece of Pleasantville history.
If coffee isn't what you're after, Pleasantville also has a pretty compelling argument for making your lunch stop here.
In 2025, Halftime Bar & Grill was named Iowa’s Best Burger, beating out the other finalists in the statewide competition. The family-owned restaurant had been encouraged by regulars to enter the competition for years, and when they finally did, they were hoping to make the Top 10. Instead, they walked away with the top spot.
That makes Halftime a pretty easy recommendation for your next burger run, especially if you’re already exploring Pleasantville. Grab a burger, settle in at the bar and grill, and see what had people across Iowa talking about this little-town favorite.
Then there’s Checkerboard, another Pleasantville staple that has been part of the community since 1975.
The restaurant started with just 10 tables in a rented building and has remained family-owned through the years. Today, the menu covers the kind of food you want when you’re looking for a good, unfussy meal: pizza, burgers, sandwiches and other comfort-food favorites.
But ask a local what you should order and there’s a good chance the onion rings will come up. They’re made in-house and have become one of Checkerboard’s specialties, making them a pretty good addition to whatever else you decide to order.
So the next time you’re heading through Pleasantville, give yourself a little extra time. Start with coffee at the original Smokey Row, grab Iowa’s Best Burger at Halftime, or make your own call on whether the Checkerboard onion rings live up to the hype.
We think Pleasantville is worth finding out for yourself.
