This December, enjoy live performances with crisp drinks and good eats in the heart of a true Texan ice house. Photo: Otto’s Ice House
Live Music All Month at Otto’s Ice House on the San Antonio River
Otto’s Ice House, your relaxed, riverside watering hole at the Pearl, is rolling out a fresh lineup of artists for December, and the vibes couldn’t be better. All shows are free, all-ages, and held on the backyard stage beneath the shady trees along the San Antonio River. (Otto’s Ice House, 2025)
Throughout the month, guests can enjoy soulful rock, authentic Americana, and talented folk troubadours who bring a genuine Texas energy to every song. Each artist carries a distinctly local spirit that pairs perfectly with the easygoing charm of this iconic ice house.
While you soak in the music, grab an ice-cold drink and savor Otto’s favorites like the Cantina Queso, Hill Country Deluxe Smashburger, Otto’s Last Shot, and more. It’s a welcoming spot to “come as you are,” trade tallboys, and enjoy community, all in one of San Antonio’s most scenic settings.
From Diwali to BBQ, there’s something for everyone this fall. Photo: Pearl
🎃 October at Pearl: A Month Full of Music, Food, and Community Fun
Fall has officially arrived, and there’s no better place to soak it all in than Pearl. As the air turns crisp and the days grow shorter, Pearl transforms into a vibrant hub of activity — filled with live music echoing through the courtyards, the scent of barbecue and baked goods drifting from the Food Hall, and the joyful buzz of friends and families gathering under twinkle lights. (Pearl, 2025)
Whether you’re here for the flavors, the fashion, or the fun, October is packed with can’t-miss events for every mood and moment.
Below is your guide to everything happening across Pearl this month — from one-night-only experiences to free community favorites that make Pearl the heart of San Antonio in the fall.
🌟 One-Night-Only Events
Runway at Stable Hall
📅 Thursday, October 16 A fashion show co-chaired by Cody Shown and Lisa Longoria Scott, benefiting the San Antonio Food Bank’s flood relief efforts. Voted Best Fashion Show in San Antonio. 💲 18+ | Ticketed Event
📅 Saturday, October 18 A first-of-its-kind gathering of 10 celebrated pitmasters. Enjoy BBQ tastings, live-fire demos, craft beverages, and live music — all family-friendly. 💲 General Admission: $77.08 (taxes & fees included) 💲 VIP: $146.39
📅 Sunday, October 19 Celebrate Ladino’s 3rd birthday with bites from Mezquite, Pullman Market, and The Jerk Shack, plus live music, balloon art, and face painting. 💲 Adults: $55 (includes 5 food & beverage tickets) 💲 Kids: $20 (includes 2 tickets)
📅 Wednesday, October 22 Celebrate the Festival of Lights with themed vendors, delicious food and drinks, live entertainment, and cultural showcases. A family-friendly evening of light, love, and community. 💲 Free Event
📅 Friday, October 31 The Y2K throwback dance party returns to Stable Hall! Bring your best Halloween costume and relive the early 2000s in style. 💲 Tickets: $20–$31
📅 Every Monday starting October 20 | Sunset at Pearl Park Catch your favorite films under the stars! Bring a blanket or chair and grab snacks from the Food Hall. 💲 Free / Cost of purchase
Pearl Farmers Market
📅 Every Saturday Shop local produce, meats, and handmade goods from South Texas farmers and ranchers. 💲 Free / Cost of purchase
Pearl Makers Market
📅 Every Sunday Explore culinary-inspired home goods and one-of-a-kind artisan finds. 💲 Free / Cost of purchase
Si Art San Antonio Pop-Up Market
📅 Saturday, October 18 | Larder, Brewmeister Alley Discover ceramics, photography, paintings, and prints from local artists. 💲 Free / Cost of purchase
📅 Sunday, October 19 Celebrate San Antonio artist Chavela’s debut album live. 💲 Ticketed Event
Performances at Jazz, TX
📅 Ongoing From Broadway reimaginings to Latin Jazz Nights, there’s always something new on stage. 💲 Ticketed Events
Live Music at Otto’s Ice House
📅 Fridays by the River Relax with a drink in hand, river views, and live country tunes. 💲 Free / Cost of purchase
Sternewirth Sessions at Hotel Emma
📅 Sundays, Mondays, and Wednesdays Enjoy a rotating lineup of Texas and national artists at the cozy tavern inside Hotel Emma. 💲 Free / Cost of purchase
✨ No matter your vibe—music, food, fashion, or fitness—there’s something happening for you this October at Pearl. Grab your friends, mark your calendars, and make the most of fall in San Antonio!
SA Examiner 