Most Baltimoreans have experienced the indulgent hedonism of the iconic Fractured Prune donut, but soon they won’t have to go downy oshun to do it. That’s right, friends, a Baltimore City Fractured Prune is in the works.
Daniel Windon, CEO of Fractured Prune Donuts, announced the plans mid-August. The first Fractured Prune donut shop opened in 1976 in Ocean City, Maryland.
Windon spoke to Baltimore Fishbowl about his plans for expansion, which he hopes will stick like cinnamon sugar to the maple glaze on the French Toast donuts that so delight his customers.
A franchise owner for nearly 20 years and an Ocean City resident, Windon started off buying an already-existing Fractured Prune shop in West Ocean City and operated it as a side job. At the time he was a real estate agent, and after the market crashed his donut shop did the opposite and began to grow.
“It started to become an actual, more full-time job than just what it had initially been,” Windon said. “I grew that one store into eight locations down here. Then I ran all eight of them, so I literally would jump from one shop to the next. I was completely hands-on every day at every location.”
In 2019, the CEO wanted to sell the company and offered it to Windon, who said yes and never looked back. Almost immediately, he had to contend with the COVID-19 pandemic but managed to keep his stores afloat. In October 2025 Windon got the itch to do more, and he made the move to open another franchise. The legal documents were completed in March 2026 and around Memorial Day he was ready to launch the marketing campaign for a Baltimore store and the search for a franchise owner.
This is not the first attempted expansion for the Fractured Prune shops. Under the previous CEO, a rapid period of growth in 2015 saw shops opening as far away as California, Arizona, and Colorado. He was even eyeing opening stores in Hong Kong, Saudi Arabia, and Canada. That never materialized, and the U.S. expansion peaked at around 30 stores nationwide.
Windon said there are currently 15 locations across Maryland, Delaware, and New Jersey. He approaches expansion through a different lens than his predecessor, focusing on fit for location and finding the right franchise owner for each location rather than scope and scale. He has narrowed down around 100 applications to four or five about whom he feels very optimistic.
“I want to make sure that they have the same drive and passion that that I do,” he said. “I want to make sure that the people that we choose are the right fit.”
What made Windon decide on Baltimore for a new location?
“Honestly, it’s more like the people from Baltimore chose me,” Windon said.
Customers often say he should open a store in their hometown, or that they would like to open a store in their hometown, and it happens that most his Ocean City customers are tourists from Baltimore, Washington, D.C., and Philly. Most residents are familiar with the brand already.
“They get the concept, [where] they live – wherever that happens to be – and they know the fit,” Windon said. “If it would fit, then I just kind of come in and put my thoughts over top of it to make sure that it’s the right fit. But my biggest motivation for the area, the generally surrounding area, is taking the concept from the beach.”
In this case, from the beach to Baltimore. That Baltimoreans are already existing customers made the decision even easier.
“It’s our 50th anniversary this summer, so we’ve been here 50 years,” Windon said. “It’s become rather like a bucket list, iconic-type place.”
