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Route 66 @ 100

Lawndale Pop-Up Spot celebrates 

What is Happening?

Route 66 is the most famous road in America. As Nat King Cole famously sang, it goes from Chicago to LA, and has since its inception as the nation’s first federal highway in 1926.

In Chicago, Route 66’s longest section is North Lawndale’s own Ogden Avenue. The Lawndale Pop-Up Spot is thrilled to partner with a number of organizations to celebrate Route 66 @ 100 through a series of arts, culture, history, and educational initiatives.

This project is funding in part by the City of Chicago’s Department of Cultural Affairs and Special Events via their Neighborhood Access Program.

❋ Elvin Explores Route 66 Coloring Book

We are proud to help sponsor the newest edition of the “Elvin Explores” coloring book series - Elvin Explores Route 66 in North Lawndale. We’re also proud to welcome a new member to the North Lawndale family - an Elvin mascot, coming soon to an event near you!

❋ Butterfly Benches

Route 66 in Illinois is part of the monarch butterfly’s annual migration path. To honor this spirit, we are installing a number of butterfly shaped benches in key spots in North Lawndale.

❋ Route 66 Community Exhibition

Starting in September 2026, we will have a community curated exhibition telling stories of North Lawndale and Route 66.

❋ Community Events

Check out our calendar of Route 66 Centennial events, from June through November, 2026!

Stay connected!
Elvin Explores Route 66 in North Lawndale

About the book

Coming soon

Butterfly benches

Details coming soon

Route 66 and Lawndale exhibition

Coming soon…

Route 66 Events Calendar

Updated calendar coming soon…

  • "North Lawndale is a vital part of Chicago's history, present, and future, and Route 66 is a centerpiece of our community."

    Community Leader

  • "Black history is American history. Period."

    North Lawndale resident

  • "It's long past time that Chicago embrace its legacy as the starting point of Route 66, and fully invest in the neighborhood that introduces Route 66 travellers to our great city!"

    Cultural worker

Get Involved

  • Browse our upcoming events to find the one that feels right for you. We host events year-round in all different locations and climates.

  • Sign up and pay all required fees to reserve your spot. If plans change, you can cancel up to 14 days before the retreat start to receive a 50% refund.

  • After booking, we'll send you a Welcome Packet with everything you need to know—detailed schedules, packing list recommendations, add-ons to consider, and more.

  • We'd recommend booking your transportation to and from the event as soon as possible, to ensure you can arrive without any complications or delays.