Downtown Bloomington’s next business challenge may not be a lack of customers, but a lack of successors. Navigating small business trends and demands is challenging. Pivoting is sometimes necessary.
Roughly 40 downtown Bloomington businesses are more than 40 years old, making them part of the city’s “legacy business” class: places that are not just storefronts, but local landmarks. Many were opened or long operated by Baby Boomer owners who are wanting a change of pace as they approach retirement age. That raises a difficult question for Bloomington: what happens when the people who built these businesses are ready to try something different, step away entirely or substantially change the culture of their business?
The issue is already visible. The Trojan Horse, a part of the downtown community for 48 years, plans to move to Ellettsville this summer to expand. Bicycle Garage, after 45 years on East Kirkwood Avenue, has relocated to South Morton Street along the B-Line Trail. Downtown is still missing Café Pizzeria. These examples show how even beloved, long-running businesses can be reshaped by needs, trends, environmental, social, parking, construction and economic pressures. They will be missed from downtown.
National data suggests Bloomington is not alone. Main Street America’s Spring 2026 Small Business Survey found that 11% of surveyed businesses identified as historic or legacy businesses, and one-third of legacy business owners were Baby Boomers. The same survey found that more than 60% of legacy businesses described themselves as destinations drawing customers from outside their communities. That makes succession more than a private business decision. When a legacy owner retires moves, closes without a buyer, downtown can lose institutional memory, local character and a reason people come downtown in the first place.
For Bloomington, the trend points to a need for earlier succession planning, stronger connections between retiring owners and younger entrepreneurs, and community support for keeping landmark businesses.
Multiple Bloomington businesses have already demonstrated successfully passing down ownership is possible. For example, Bloomington Bagel Company, Lennies and Malibu Grill were all purchased by former employees, allowing the businesses to continue under someone who already understood the culture. Mirth offers a similar story: former employees of Relish and Lennie’s came together to create a new downtown store that has been successful for seven years and is now expanding. Uptown Café is keeping ownership in the family transitioning to the next generation. These stories show that with the right planning, longtime businesses can evolve while keeping local knowledge, relationships and community identity at the center of downtown Bloomington’s future.
If you or your business would like to get involved in a specific project or learn more, please email info@downtownbloomington.com.
Talisha Coppock is executive director of Downtown Bloomington Inc. and the Bloomington Convention Center.
This article originally appeared on The Herald-Times: Successors needed to keep downtown Bloomington thriving
Reporting by Talisha Coppock, It’s Your Business / The Herald-Times
USA TODAY Network via Reuters Connect
By Talisha Coppock, It's Your Business | USA TODAY Network
