Old Fashioned Donuts – which just celebrated 50 years and is home to arguably the best glazed donut in the city – is Michigan Avenue’s most famous merchant. Not the Michigan Avenue of the Magnificent Mile but the “other Michigan Avenue” in Chicago’s Roseland neighborhood.

A self-contained shopping district on the South Side, this once-vibrant stretch of urban commercial real estate has weathered white flight, segregation and de-industrialization that began in the 1960s.

“This is a main street that is largely intact,” said Maurice Cox, commissioner of the city’s department of planning and development. “Behind a lot of these storefronts that have been covered with siding are the historic buildings that were here in the 1800s. So you peel off that layer, you will find the historic fabric is intact. And we believe that because it’s still a functioning retail corridor, it has the potential to have a makeover.”

To get a sense of how much of a makeover the corridor would need, I walked the blocks from 111th and 115th streets in October. What I found surprised me: While there is certainly ample evidence of neglect – 52 vacant buildings and 10 vacant lots – I counted 15 clothing stores, three furniture stores, three barbershops, two nail salons, a church, a bank, a daycare, two pharmacies and five restaurants, among a total of 48 businesses or organizations that dot the four-block stretch today.

One of those businesses is Ware Ranch Steakhouse, a diner with homemade pancakes, salmon croquette and a massive steak named after John Wayne. Cowboy motifs hang on the bright yellow walls. The sit-down restaurant opened in 2018 but had a fire in 2020. It reopened this past summer.

Judy Ware owns the restaurant with her husband. They live in the neighborhood and she has a vision for Michigan Avenue.

“There are older people in this neighborhood who would like to see stuff we would like to wear,” Ware said about desirable retail, such as more clothing-store options. “More restaurants. I would love to see a movie theater.”

Down the avenue a ways, a brown vinyl facade covers a beauty supply store. The storefront is a bit of a mirage because underneath is the historic facade of brick that harkens back to the sepia-toned days of the commercial corridor.

Roseland is the last of the 10 communities targeted for redevelopment under the city’s ambitious INVEST South/West economic program; Michigan Avenue is a centerpiece. Compared to other neighborhoods struggling with vacant land, this part of Michigan Avenue has comparatively few – only 10 empty lots, according to my informal count.

The city owns three vacant lots in the vicinity, including the former Gately’s department store at the corner of 112th and Michigan. The city’s vision for that location is housing with retail stores. The planned CTA Red Line extension is a few blocks south near 116th and Michigan, and the city wants to develop the land next to it. And there’s a third vacant lot that was the site of a movie theater that Cox sees as a blank canvas.

Other elements of the city’s revitalization plan include affordable housing, transit-oriented development and retail connected to the emerging medical district anchored by the nearby Roseland Community Hospital. Normally when the city looks to redevelop land it owns, its department of planning and development, which Cox leads, puts out a request for proposals.

“We found that that was an unfair barrier for a lot of Black and brown developers,” Cox said. Instead Cox says the city is asking for a request of qualifications for Michigan Avenue. Developers and architects will then be matched up to create a joint venture. Those teams will each get a $20,000 to $30,000 stipend from a philanthropic foundation to pitch a proposal.

“We eliminate that barrier of smaller emerging developers from being able to compete and having to advance those dollars to come up with their proposals,” Cox said.

The community will hear the proposals by March 2023.

“There are a number of legacy businesses like the donut shop that suggest that there’s still enormous economic vibrancy here. What they need is assistance, both to market what’s here, to have a makeover and to change their public appearance to shoppers,” Cox said.

In 2020, the city formed a Greater Roseland Neighborhood Roundtable to gather input.

Joyce Chapman, president of the Far South Chicago Coalition, said she understands that residents have been frustrated with the past fits and starts of neighborhood redevelopment.

“They’ll say ‘oh, it will never happen, oh it’s been said before,’” Chapman said.

But she believes this time is different.

“Our community partners now understand the process. How can I speak to you in this interview, if I didn’t have the buy-in to our community? I live and breathe this community,” Chapman said.

Because those vacant lots on Michigan Avenue are assets waiting to flourish. The corridor doesn’t have to replicate a sepia-toned past but rather usher in a new era of commerce for the community.

Natalie Moore is a reporter on WBEZ’s Race, Class and Communities desk. You can follow her on Twitter at @natalieymoore.