Retro on Roscoe Festival Returns with Early January Planning for Expanded 2026 Edition

By Socialhood News · Il/Chicago/Roscoe Village · January 4, 2026

Roscoe Village residents are already looking ahead to one of the neighborhood's most anticipated annual events, with early planning underway for Retro on Roscoe 2026. The popular festival, which transforms the tree-lined streets of Roscoe Village each September, features Chicago's top talent and entertainment on three main stages alongside artisans, antique vendors, and local merchants providing a shopping experience that's second to none.

The 2025 edition of the festival saw record attendance with visitors enjoying summertime samplings and tasty treats from local restaurants while exploring the event's signature Antique Car Show, which showcased over 50 antique, classic and muscle cars. The festival's Family Area, recognized as one of the best in Chicago, offered top-notch talent, games, crafts, and activities for all ages. As the primary fundraising event for Roscoe Village Neighbors, proceeds from the festival support major community improvements including streetscape projects, public art installations, local school resources, and various community events throughout the year.

Roscoe Village Neighbors, the 501(c)(3) nonprofit organization serving the area bounded by Addison Street and Belmont Avenue from Ravenswood Avenue to the Chicago River, continues its commitment to enhancing the quality of life for both residents and merchants. Community members interested in participating in early planning for the 2026 festival can connect with organizers through the Roscoe Village Neighbors website.

Sources:
1. https://www.roscoevillage.org/Retro-On-Roscoe/
2. https://chicagoevents.com/event/retro-on-roscoe/