Music, comedy, and Alamo City flavor are on the entertainment menu as May turns up the heat. Sip and stroll through our signature event, the 2026 CultureMap San Antonio Tastemaker Awards, or sing along with Silversun Pickups and Robert Earl Keen. Check out the top seven things to do in San Antonio this weekend. For a complete list of events, click over to our calendar.
Thursday, May 14
2026 CultureMap San Antonio Tastemaker Awards
Our annual celebration of San Antonio’s top bars and restaurants returns with equal parts flavor and fanfare. Tickets to this signature tasting event and awards ceremony at Briscoe Western Art Museum include chef-prepared bites and specialty cocktails all night long. Guests will also have a chance to meet and mingle with the biggest names and rising stars in the local food and drink industry. Check out our San Antonio Tastemaker Awards editorial series to learn more.
Friday, May 15
Aztec Theatre presents Bobby Lee: The Finally Tour
Comedian Bobby Lee showcases his stand-up talent live at Aztec Theatre. The actor, podcaster, and entertainer comes to San Antonio in support of his first official headline tour. He’s widely known for his role as the co-host of the Bad Friends and TigerBelly podcasts. Lee gained notoriety in the comedy industry during his tenure on MADtv. Get more information on Ticketmaster.
Saturday, May 16
Guadalupe Cultural Arts Center presents Tejano Conjunto Festival en San Antonio
San Antonio’s first and longest-running Conjunto festival continues at Rosedale Park. Attendees can expect a setlist of various Conjunto music styles made popular and played across Texas. Events are scheduled through May 18. For a complete schedule and to purchase tickets, visit the festival website.
Whiskey Riot
Sip and sample a variety of distilled options at Freeman Expo Hall. The boozy event includes more than 200 whiskies from brands across the region, country, and world for connoisseurs of all palate types to enjoy. Attendees can meet master distillers, discover new brands, and mingle with fellow whiskey fans for one high-spirited evening. Tickets are on sale now.
Robert Earl Keen and Friends: Feelin Good Again
Iconic country artist Robert Earl Keen plays the Whitewater Amphitheater. He’ll be joined by special guests Race Ricketts, Coleman Jennings, and Shelby Stone. Keen has released 12 albums throughout his career and is the voice behind hit songs such as “The Road Goes On Forever” and the classic sing-along “Feelin’ Good Again.” Find out more on Tixr.
Charline McCombs Empire Theatre presents Danae Hays: The Buckwild Tour
Comedian Danae Hays shows off her standup chops live. Hays draws her style of humor from legends like ‘Weird Al’ Yankovic, Andy Samberg, and Carole Burnett, and blends comedy with music from a fresh, female perspective. Her fanbase spans platforms like Spotify and TikTok. Save your seat on ATG Tickets.
Sunday, May 17
Aztec Theatre presents Silversun Pickups in concert
Alternative rock band Silversun Pickups performs live at Aztec Theatre. The group rose to fame in the 2000s with hit songs like “Lazy Eye” and “Panic Switch.” Their most recent album, Physical Thrills, was released in 2022. For seating availability, go to Ticketmaster.