1. Take It Back Now

Take a trip down memory lane, otherwise known as Roscoe Village, for Retro on Roscoe. The festival is celebrating its 25th year in business with oldies and throwbacks spanning six blocks and three stages. If the music isn’t enough, there’ll be vendors and local restaurants in attendance. August 12-14. starevents.com

2. Sippin’ Sampler

No matter where you are on Milwaukee Avenue this weekend, make sure it’s in the vicinity of Pilot Project Fest. The brewery is celebrating its second annual fest with a variety of beer samples, local food, and music. August 14. eventbrite.com

3. Dance It Out

Slo ‘Mo Party has been bringing the LGBTQ+ community together for eleven years through club nights, concerts, and comedy. This year at Sleeping Village, Your Godmutha Tristen and Party Mom Kristen will be hosting the event, featuring music by Lovenloops and VITIGRRL. Last but not least, there’s a celebratory mezcal tasting and Taylor’s Tacos food pop-up. August 12. sleeping-village.com

4. Outside the Lines

Chicago-based painter AJ Ainscough’s Back Outside exhibition opens this weekend at Vertical Gallery. His debut solo exhibit features 13 new works, staying true to his style that exhibits a sort of controlled chaos. August 13-September 4. verticalgallery.com

5. Big House

My House Music Fest, set in Harrison Park, will give attendees the chance to see DJ Sneak, Ralphie Rosario, and Farley Jackmaster Funk, to name a few. August 13-14. myhousemusicfest.com