Jump To: May 1 – 3 | May 8 – 10 | May 15 – 17 | May 22 – 24 | May 29 – 31
Ready to dive into a month of spring fun? San Antonio is buzzing with a fantastic mix of celebrations, cultural events, and live entertainment this May 2026.
Whether you’re looking to get your heart racing at a spring race, dance the night away at a music festival, or explore the city’s rich history and art, there’s something for everyone. From thrilling new shows and spine-tingling concerts to vibrant and festive food events, this guide has you covered.
Get ready to explore the best of what San Antonio has to offer!
This month’s highlights include the Fredericksburg Food and Wine Festival Restaurant Week, Pride River Parade and Festival, and more!
TOP PICK FOR MAY – Weekend Getaway to Galveston – La Izquierda Surf & Music Festival
Experience a different side of Texas tradition at the La Izquierda (The Left) Festival. This three-day celebration honors Galveston’s unique “Third Coast” surf culture through a fusion of live music, visual art, and community storytelling.
From the high-energy sounds of the main stage to the rhythmic waves of the longboard competition, it’s a vibrant, family-friendly weekend dedicated to beach preservation and the island’s creative soul. Perfect for a coastal retreat to kick off May.
When: Friday, May 1 – Saturday, May 2, 2026 | Fri: 2 pm – 11 pm, Sat: 9 am – 11 pm
Where: Beach Central (Main Stage) & 21st and Seawall (Beach Stage), Galveston, TX 77550
How Much: $30 General Admission (Weekend Pass); $100 VIP; Kids 10 and under are free
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Remember to check out our complete guide to San Antonio Rooftop Bar Guide, Late Night Food San Antonio, and Cheap Eats in San Antonio!
Events in San Antonio for Adults – May 1 – 3, 2026
Chicago: The Musical – Experience the legendary band Chicago live as the Rock and Roll Hall of Fame group brings decades of chart-topping music to the stage.
Image credit: Majestic and Empire Theatre
Fool House – The Ultimate 90s Party: The Millennium Tour – Step into a throwback celebration at Fool House: The Millennium Tour, a high-energy live show packed with hits from the ’90s and early 2000s. Expect a nostalgic party atmosphere complete with trivia, themed fun, and a full band performing the songs that defined the era.
Alamo City Arts presents, A Midsummer Night’s Dream – Enter a magical world as Alamo City Dance Company brings A Midsummer Night’s Dream to life through ballet. Inspired by Shakespeare’s beloved comedy, the performance follows enchanted forests, mischievous fairies, and tangled romances in a whimsical story told through dance.
FESTIVAL AUDAZ 2026 – 2nd Annual by Teatro Audaz – Discover a vibrant mix of creativity at Festival Audaz, a multi-arts event presented by Teatro Audaz. The celebration features original theatre performances alongside live music, comedy, visual art, local vendors, and food trucks.
Los Lobos w/ Greyhounds – See Los Lobos live as the acclaimed band performs the music that has defined their decades-long career.
Pan-African Festival Weekend 2026 – Celebrate culture, history, and community at Pan-African Festival Weekend, a multi-day gathering focused on the African diaspora. The event brings together performances, conversations, and cultural experiences that highlight unity and heritage.
Quiet Beats, Loud Impact Silent Disco – Dance your way through a silent disco where wireless headphones let you switch between multiple music channels.
The Barber of Seville – Enjoy the lively charm of Rossini’s comic opera The Barber of Seville, filled with romance, disguises, and clever schemes.
Image credit: OPERA San Antonio
Wine Fest: Derby Edition – Celebrate the excitement of the Kentucky Derby at Wine Fest: Derby Edition, where Sonoma County wines meet festive racing-day fun.
Image credit: Tower of the Americas
Clown Church Variety Show- Live at Rah! Rah! Room – Enjoy a night of unpredictable entertainment at the Clown Church Variety Show, a live comedy and performance event featuring music, vendors, and interactive fun.
Seven Seas Food Festival at SeaWorld San Antonio – Explore over 100 global offerings and vibrant live performances at the Nautilus Amphitheater, including iconic acts like Ginuwine, Blackstreet, and Soulja Boy.
Dining Cruises on the San Antonio River Walk – Transform your evening into an unforgettable San Antonio River Walk adventure by boarding a Paesanos Riverwalk Dining Cruise. Savor a delicious, chef-prepared meal and exceptional hospitality while the stunning riverfront views glide past your table.
Events in San Antonio for Adults – May 8 – 10, 2026
Floetry – See the acclaimed R&B duo Floetry live as Marsha Ambrosius and Natalie Stewart bring their signature blend of soulful vocals and spoken-word poetry to the stage.
Fredericksburg Food & Wine Festival Restaurant Week – Savor the culinary scene of the Texas Hill Country during Fredericksburg Food & Wine Festival Restaurant Week. Local restaurants present special menus, chef collaborations, and exclusive dining experiences throughout the celebration.
Latido Festival: San Antonio – Feel the rhythm of Mexican music at the inaugural Latido Festival, an open-air celebration featuring performances by Tucanes de Tijuana, La Mafia, and Los Herederos De Nuevo León. The event brings together music, food, and community for a lively festival atmosphere.
Image credit: Latido Festival: San Antonio
Tacos & Tequila Festival – Relive the early 2000s at the Tacos & Tequila Festival, a throwback celebration featuring hip-hop and R&B performances alongside great food and drinks.
Image credit: Tacos and Tequila Festival San Antonio
Classic Theatre presents Steel Magnolias – Experience the warmth and wit of Steel Magnolias, a beloved story about friendship and resilience among a group of women in a small Southern town.
Amazon: Andes to the Atlantic with Thomas Peschak – Join National Geographic Explorer Thomas Peschak for a visual journey along the Amazon River. Through powerful images and stories from his 396-day expedition, the presentation reveals the region’s extraordinary wildlife, ecosystems, and hidden worlds.
Chelcie Lynn: Trailer Trash Tammy The Loose Lips Tour – Catch comedian Chelcie Lynn live as she brings her outrageous Trailer Trash Tammy character to the stage.
Seven Seas Food Festival at SeaWorld San Antonio – Explore over 100 global offerings and vibrant live performances at the Nautilus Amphitheater, including iconic acts like Ginuwine, Blackstreet, and Soulja Boy.
Dining Cruises on the San Antonio River Walk – Transform your evening into an unforgettable San Antonio River Walk adventure by boarding a Paesanos Riverwalk Dining Cruise. Savor a delicious, chef-prepared meal and exceptional hospitality while the stunning riverfront views glide past your table.
The Dinner Detective True Crime Murder Mystery Dinner Show – San Antonio, TX – North America’s largest interactive comedy murder mystery dinner show is here, inviting you to solve a hilarious whodunnit while enjoying a delicious dinner. Just be warned: the culprit is hiding in plain sight, and you could become a prime suspect at any moment.
Events in San Antonio for Adults – May 15 – 17, 2026
Gimme Gimme Disco – Hit the dance floor at Gimme Gimme Disco, a DJ-driven party celebrating the timeless hits of ABBA and the disco era.
Image credit: Gimme Gimme Disco
5th Annual San Antonio Psychic & Spirit Fest – Explore the mystical at the San Antonio Psychic & Spirit Fest, featuring psychics, mediums, spiritual vendors, and themed experiences.
Candlelight: The Best of Joe Hisaishi – Hear the beloved music of composer Joe Hisaishi performed live in an intimate candlelit concert. The program celebrates iconic film scores from Studio Ghibli favorites, including Spirited Away, My Neighbor Totoro, and Howl’s Moving Castle.
Giselle – Experience the romance and drama of Giselle, one of ballet’s most celebrated works. The timeless story follows love, betrayal, and redemption through graceful choreography and emotional storytelling.
Veil & Vogue: The Bridal Showcase – Explore wedding inspiration at Veil & Vogue, a stylish bridal showcase featuring a live runway presentation of couture gowns.
Bobby Lee: The Finally Tour – See comedian Bobby Lee live as he takes the stage with his Finally Tour.
Whiskey Riot – Taste your way through Whiskey Riot, a large whiskey sampling event featuring hundreds of pours from distilleries around the world.
Image credit: Whiskey Riot Festival
Laugh Out Loud Comedy Club presents Tyler Fischer – Catch stand-up comedian Tyler Fischer live as he brings his quick wit and viral humor to the stage. The New York-based performer blends sharp observations with stories from his career in comedy and entertainment.
Classic Theatre presents Steel Magnolias – Experience the warmth and wit of Steel Magnolias, a beloved story about friendship and resilience among a group of women in a small Southern town.
Seven Seas Food Festival at SeaWorld San Antonio – Explore over 100 global offerings and vibrant live performances at the Nautilus Amphitheater, including iconic acts like Ginuwine, Blackstreet, and Soulja Boy.
Dining Cruises on the San Antonio River Walk – Transform your evening into an unforgettable San Antonio River Walk adventure by boarding a Paesanos Riverwalk Dining Cruise. Savor a delicious, chef-prepared meal and exceptional hospitality while the stunning riverfront views glide past your table.
Events in San Antonio for Adults – May 22 – 24, 2026
Candlelight: Neo-Soul and Hip-Hop Favorites – Experience neo-soul and hip-hop classics in a candlelit concert setting. The program features instrumental interpretations of songs by artists such as Lauryn Hill, Frank Ocean, Prince, and Alicia Keys.
Hometown Half Marathon & 5k/10k – San Antonio – Take part in the Hometown Half Marathon and 5K or 10K, a welcoming race designed for runners of all experience levels.
Carin Leon – See regional Mexican star Carín León live as he brings his powerful vocals and genre-blending sound to the stage.
Classic Theatre presents Steel Magnolias – Experience the warmth and wit of Steel Magnolias, a beloved story about friendship and resilience among a group of women in a small Southern town.
Dining Cruises on the San Antonio River Walk – Transform your evening into an unforgettable San Antonio River Walk adventure by boarding a Paesanos Riverwalk Dining Cruise. Savor a delicious, chef-prepared meal and exceptional hospitality while the stunning riverfront views glide past your table.
The Dinner Detective True Crime Murder Mystery Dinner Show – San Antonio, TX – North America’s largest interactive comedy murder mystery dinner show is here, inviting you to solve a hilarious whodunnit while enjoying a delicious dinner. Just be warned: the culprit is hiding in plain sight, and you could become a prime suspect at any moment.
Events in San Antonio for Adults – May 29 – 31, 2026
Stayin’ Alive: One Night of the Bee Gees – Celebrate the music of the Bee Gees with Stayin’ Alive, a tribute concert packed with the group’s biggest disco and pop hits.
Image credit: Emporium
Paula Poundstone – Spend an evening with comedian Paula Poundstone as she delivers her sharp observational humor and spontaneous wit on stage. Known from NPR’s Wait, Wait… Don’t Tell Me! and numerous specials, Poundstone brings decades of comedic insight to her performance.
Pride River Parade & Festival – Celebrate LGBTQ+ pride at the Pride River Parade & Festival along the San Antonio River Walk. Colorful floats, lively performances, and a festive atmosphere bring the community together in a joyful celebration.
Image credit: Visit San Antonio
Slice Swap: A Cake Party at Clementine – Bring your favorite cake and trade slices with fellow dessert lovers at Slice Swap, a fun community gathering centered around baking and sharing. Guests leave with a mix of new flavors and a chance to connect with other cake enthusiasts.
Tyler Henry Hollywood Medium – See medium Tyler Henry live as he shares stories about his work communicating with the other side and offers audience readings.
Classic Theatre presents Steel Magnolias – Experience the warmth and wit of Steel Magnolias, a beloved story about friendship and resilience among a group of women in a small Southern town.
Dining Cruises on the San Antonio River Walk – Transform your evening into an unforgettable San Antonio River Walk adventure by boarding a Paesanos Riverwalk Dining Cruise. Savor a delicious, chef-prepared meal and exceptional hospitality while the stunning riverfront views glide past your table.
Keep the good times rolling with our updated San Antonio Things To Do This Weekend roundup of events, festivals, and nightlife across the city.
