Retro on Roscoe is a 3-day street festival celebrating vintage vibes, live music, and family fun in the heart of Roscoe Village on Chicago's North Side, returning for its 30th annual edition in 2026. Set against the neighborhood's charming, tree-lined streets, the festival features two stages of non-stop live music, a dedicated kids area with inflatables, games, and crafts, an arts and crafts market with artisans, antique vendors, and unique merchants, local restaurant participation from the neighborhood's top eateries, and the Retro Antique & Classic Car Show showcasing 20+ stunning antique, classic, and muscle cars. The festival runs Friday 5pm–10pm, Saturday 12pm–10pm, and Sunday 12pm–8pm, drawing crowds to Roscoe Street at Damen Avenue. Roscoe Village is known for its historic architecture, trendy boutiques, cozy cafés, and top-rated restaurants, making it a favorite among families and young professionals. The event is produced by Roscoe Village Neighbors (RVN), a 501(c)(3) nonprofit dedicated to serving the community within the boundaries of Addison Street to Belmont Avenue, from Ravenswood Avenue to the Chicago River. Audience Information: - Age: 25–54 - Gender: 49% male, 51% female - 58% home renters - Education: College degree or higher - HHI: $150K+