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Program Spotlight: Bike Rides Power Community Connections in Chicago

January 26, 2023 | Program Spotlight: Bike Rides Power Community Connections in Chicago | By: Frankye Payne, Director of Chicago Main Streets at Main Street America | 

Equiticity founder, Oboi Reed, leads a community bike ride in Chicago’s Pullman neighborhood. Credit: Oscar Sanchez.

Main Street America believes that the best approach is one that comes from within the community itself. Something that is reflective of the place and people that are looking to revitalize a neighborhood that they are passionate about. It was our great fortune last year to connect Equiticity, a grassroots racial equity movement, with the Corridor Managers of Chicago's INVEST South/West initiative to bring commercial corridors to life through a series of bicycle rides.
Under the guidance of Equiticity founder, Oboi Reed, and with support from Divvy (Chicago’s bike share system), the communities of South Chicago, Humboldt Park, Avalon Park/South Shore, and Roseland/Pullman showed up and showed out in some classic summertime Chi weather.

Each ride had its own playlist, a costume or community merch aspect, and a connection to local culture and flavor that invited participants to fall in love with these corridors like kids on summer vacation.

Left: Stopping to enjoy a mural in South Chicago. Right: Connecting with residents before riding out. Credit: Oscar Sanchez.

In South Chicago we rode past the annual Meeting of Styles mural fest and supported vendors at Bridges Puentes.

Left: Ride organizers and participants pause for a photo. Right: Organizers partner with a local business to support the ride. Credit: Oscar Sanchez.

Humboldt Park brought a super experience—superhero that is! And the capes were flying past Cultural landmarks and new storefronts.

Left: New Black Renaissance band providing a soundtrack for the ride in Avalon Park and South Shore. Right: A ride participant and community supporter stands in front of a community mural. Credit: Oscar Sanchez.

Have you ever put a live band on the back of a truck? Avalon Park and South Shore teamed up with the New Black Renaissance band to get bikes and booties swaying as riders passed historic artworks. We even picked up a singer along the route!

Left: Main Street America staff engage with community members. Right: Riders stop to pick up a sweet treat and support a local business. Credit: Oscar Sanchez.

During the ride through the Pullman neighborhood, we donned Halloween costumes and celebrated the new and old: from starting at the new National Monument Park to stopping at the Pullman Community Center and the Old Fashioned Donuts shop.

What was the best part of this experience? That as soon as Chicago thaws out this year, we will be expanding this opportunity to a total of 9 neighborhoods. We hope to see you on the South and West Sides this summer as we celebrate the wins of the Invest South/West corridors the best way possible: together as a community.

Our communities are excited to experience the 2023 ride series. To learn more and find up-to-date information about upcoming rides please visit