There’s a cheerful sign on the sidewalk outside of the Happy Apple Pie Shop, 226 Harrison St. in Oak Park. It reads, “Pie Today!” The question for owner Michelle Mascaro is whether there will be pie tomorrow. As she contemplates retiring, Mascaro is searching for a new owner to keep the dough rolling.
Mascaro opened the shop eight years ago. Her goal was not only delicious pie, but also a welcoming work environment for people with and without developmental and intellectual disabilities.
“We decided to start it because my oldest child, my daughter, has an intellectual disability and severe anxiety disorder,” Mascaro said. “Everybody has to learn how to have a job.”
At age 22 young people with disabilities age out of state-sponsored learning programs. Employment is the next challenge.
“We thought we’d start something she and her friends like to do. Like everyone, they like to make food,” she said.
Happy Apple’s opening was right before Thanksgiving. A perfect time for pie. The pastries were a hit from the very beginning.

Each day a variety of both sweet and savory pies are available for purchase by the slice or whole pie. Advance orders are accepted and appreciated. And catering orders are a big part of the business too.
Apple pie is always on the menu, but recent flavors have included chocolate chess and, for St. Patrick’s Day, chocolate Guinness. Fruit pies follow peak harvesting seasons, so no peach pie in the winter. Savory flavors can be seasonal too, like the recent corned beef pot pie. Chicken pot pie is always on the menu or customers get grumpy, according to Mascaro.
“We built a wonderful community. I call it the pie community. We have some regular people that come from Hyde Park, come from out in the western suburbs, up in the northern suburbs, and it’s just always nice to get to see them again and welcome people,” she said.
Her workforce is dedicated too.
“I like to think of people with abilities who work here, because that’s really how we focus on what’s the ability,” Mascaro said. “I have staff who say, this is the job I want for the rest of my life.”
Prep work is done during the day. Most employees work a two- or four-hour shift, depending on what is best for them. Pies are baked in the evenings. Like a lot of foods, pie is better when it’s had some time to set up for sale the next day.
Funnily enough, her daughter doesn’t work at the shop.
“Her attitude is — you’re my mother and I don’t want to work with you,” Mascaro said. “That’s actually pretty ordinary, right? She works at the Park District of Oak Park.”

That understanding is a hallmark of everything Mascaro does. Lead with kindness is a mission.
The reason for Mascaro’s retirement is doctor’s orders. It’s a good time to break from days and nights crafting pies and focus on other, less strenuous ideas that she has.
“I’m beyond retirement. I want to make sure that whoever takes this over has the capacity and the understanding to do this. And I think there are many creative ways to do it,” she said. “I want it to be that we started something that has a life and continues. That something was begun here, a network of kindness, community and good pie.”







