Among the riders was Alana Martin, who grew up in Philadelphia, but now looking to make Chicago home.
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"I am eager to become a first-time homeowner and Englewood is an area of interest for me," Martin said.
That's why she boarded the trolley Saturday morning, joining Englewood residents, stakeholders and community organizations to take a look at what the area has to offer.
"This is a good opportunity to come in and reimagine how Englewood would be, could be," said Englewood resident Deborah Payne.
They're trying to solve a pretty big problem.
Okechukwu Chika was also looking to buy a house in Englewood.
"I think it's earned a bad reputation over the past couple of years," said Chika. "People turn their nose up at it. Not me."
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Pushing more people to consider homeownership and giving residents an opportunity to meet with housing experts and learn about grants and financing.
"We want to show that they are creating and originating loans in this community and really helping residents to keep their homes," said Rashanah Baldwin of Neighborhood Housing Services of Chicago.
All big steps in re-envisioning, reclaiming and reimagining Englewood.
"It's just the fabric of this community is beautiful the people who live here are beautiful people need to take a chance and get to know Englewood beyond the news," said Martin.
The project is also hoping to attract developers who are interested in developing responsibly in this neighborhood.