Since its inception more than a decade ago, the Happy Apple Pie Shop has had two goals: employ people with and without disabilities and, in the words of founder Michelle Mascaro, “make really delicious pie.”
“It’s very, very difficult for people with intellectual and developmental disabilities to find work,” said Mascaro. Mascaro and her wife were thinking about their daughter Emma, who has an intellectual disability, when they founded the shop. By establishing Happy Apple Pie, Mascaro aimed to create more employment opportunities for disabled people and inspire other businesses to do the same.
Mascaro founded the business in 2015; work started to establish its current location a year later. That location — 226 Harrison St. in the Oak Park Arts District — is itself unique. Mascaro worked with the owners of the building to ensure a fully accessible space for all her employees: Furniture is easy to move, the bathroom is fully accessible, the front door is automatic and the space is open enough for employees and customers to see one another.
Mascaro has led the award-winning pie shop in Oak Park since its opening day. Now, she is stepping back from the bakery. Her retirement has been a long time coming — she has been searching for a new owner since early last year. It wasn’t until she was approached by the Chicago area chapter of Easterseals, a nonprofit that supports people with disabilities, that Mascaro felt able to sell.
Sara Ray Hallman, the president and CEO of the Easterseals serving Chicago and Rockford, said Happy Apple Pie’s social enterprise mission and core philosophy aligned well with Easterseals. Easterseals already runs a similar social enterprise in Chicago, HB Threads, which also employs people with disabilities to help them develop career skills.
“This seemed very much like a natural fit for us,” Hallman said. “We were very like-minded in the way that we thought about serving people with disabilities.”
For Mascaro, Easterseals’ mission and experience with similar enterprises was an important factor in her decision. Mascaro was looking for a buyer who would be able to run the shop without a lot of help from her. With Easterseals, Mascaro says there is a plan to transition her away from long hours on her feet, which her doctor has advised was a good idea.
It was also important to Mascaro that her employees be allowed to stay at the shop, which Easterseals agreed to.
“They had the sense of community, I believe, that will still engage all of our customers and create a community-oriented space,” said Mascaro, who said she is looking forward to watching the business she founded grow.

What’s next for Happy Apple Pie?
Easterseals is already planning on expanding Happy Apple Pie’s operations, bringing on new staff in addition to those retained. Among the planned expansions is a partnership with Dark Matter Coffee to offer coffee and espresso beverages. Easterseals is also partnering with Sarah Stenger, who co-owns Prairie Grass Cafe in Northbrook, and Michael Ciapciak of Bang Pie and Biscuits in Logan Square. Pastry chef Margie Sprehe will take over the shop’s day-to-day operations. Throughout the transition, Mascaro and Sprehe will work together to transition Happy Apple Pie’s operations.
“We want to make sure we have a true understanding of what the operation is currently like before we come in and suggest any changes,” Hellman said. “We want to be respectful of that history and trajectory.”
Hellman says Easterseals is working to acquire permits for some renovations, including some that will allow for the installation of an espresso machine. Once permits are secured in the next few months, Hellman says they will be able to announce an official reopening date, which will follow a brief period of closure.
Even with new offerings, pies will still be the core of Happy Apple Pie. The sign in front of the shop, which draws customers from all over the Chicago area, reads simply: “Pie Today.”
“I could write a book about what ‘Pie Today’ means to people,” Mascaro said. “It’s homey, it’s comfortable, it may invoke memories for you, it may create memories for you. It just means ‘come on in.'”




