February marks the start of rodeo season in San Antonio, and Pearl is saddling up with a month-long lineup of events to celebrate. From the first-ever Cowboy Heritage Festival and free Two-Step Tuesday dance classes at Stable Hall to a Movie Monday screening of the classic cowboy duo in “Toy Story 2,” there’s something for everyone all month long.
We’re here to corral all the details so you can plan ahead and save the dates for your next visit to Pearl. Be sure to make loose plans – we have a stable of ideas ready for you.
Cowboy Heritage Month Events at a Glance
- Cowboy Heritage Festival
- Two Step Tuesdays at Stable Hall
- Hotel Emma Rodeo Dinner Series
- Saturday Pearl Farmers Market Activations
- Free Live Country Music at Otto’s Ice House
- Movie Mondays at Pearl Park
- Where to Get Rodeo Ready
More February Events at a Glance
- Porc Slap x Cape Bottle Room Pop Up
- National Marg Day at Mezquite
- Run Club Meetup at Coopers Row & Otto’s Ice House
- Heated Rivalry Dance Party at Stable Hall
- Jazz Brunch
- Jazz Dinner
- Bi-Annual Sidewalk Sale
- Big Game Watch Party at Stable Hall
- Alternative Big Game Watch Party at Jue Let
- Rescheduled Movie Monday – “Casablanca”
- Valentine’s Day Residency at Jazz, TX
- Valentine’s Day at Pullman Market
- Galentine’s Bouquet and Bubbles Workshop at High Street Wine
- Galentine’s Party at Sternewirth
- Galentine’s Day at Cape Bottle Room
- ACTIVATE Boot Camp at 1100 Springs Plaza
- Pullman Market’s Charity Chili Cook Off
- Concerts at Stable Hall
- Maker Break Club at Niche
Save the Date: Cowboy Heritage Festival
Friday, February 7 | 3:00 to 7:00 PM
The kickoff to Cowboy Heritage Month is slated for February 7 and is our inaugural Cowboy Heritage Festival. This free, family-friendly event transforms Pearl into a celebration of everything that makes South Texas cowboy culture legendary. Expect live music, unique food and drink, demonstrations of traditional vaquero skills, and rodeo-style activities for all ages.
Stay tuned to our social media and subscribe to our newsletter to be the first to know all of the details.
A Month of Rodeo Spirit
The vaquero spirit rides on all month long with special events like a Movie Monday screening of “Toy Story 2,” free dance classes, market pop-ups, and more.
Two-Step Tuesdays at Stable Hall offer the perfect excuse to dust off your boots, bring your partner, and learn (or show off) your moves on the dance floor. Check out the schedule:
- Tuesday, February 3, featuring live music by the Jerry DeLeon Band at Stable Hall
- Tuesday, February 10 at Pearl Park
- Tuesday, February 17 at Pearl Park
- Tuesday, February 24, with live music by the Joe Panther Band at Stable Hall
Doors open at 6:30 PM, with lessons beginning at 7:00 PM, and the dance floor opens right after at 8:00 PM.
Hotel Emma is hosting a series of exclusive dinner parties featuring meticulously aged spirits and seasonally driven three-course meals. Reserve your seat in Supper’s Swiggle Key private dining room on February 6th or February 27th to experience legendary whiskey lineups from the historic Buffalo Trace Distillery or rare, ultra-aged expressions from the British Isles.
Tickets for Friday, February 6, are available here.
Tickets for Friday, February 27, are available here.
Saturdays at the Pearl Farmers Market feature rodeo-themed fun throughout the month, including live country music and skilled demonstrations, including a trick roper.
Live music on the patio at Otto’s Ice House is the place to be for classic country tunes, scenic river views, and a cold one with your herd. Make sure to follow them on Instagram to get the latest lineup, and don’t forget to try their latest happy hour offering. Kick back, cheers with friends, and listen to live music on Thursdays, Fridays, Saturdays, and Sundays.
The February 16 Movie Monday screening features everyone’s favorite cowboy-and-cowgirl duo, Woody and Jessie. “Toy Story 2” is the evening’s feature film, so ride like the wind to snag your Pearl Park spot early. Films begin around 6:30 PM.
Where to Get Rodeo Ready
Looking to add some southern charm to your wardrobe this rodeo season? Pearl’s retailers are wrangling up the season’s best outfit inspo. Check out our picks for where to shop to get rodeo-ready:
- King Ranch Saddle Shop: Shop a selection of men’s and women’s clothing featuring embroidered western shirts and a variety of button-down options. Prefer to accessorize? Pick up a selection of items and get them embroidered in-store!
- The Tiny Finch: Cowboy-chic is in, and The Tiny Finch has the perfect accessory to go with your Two Step Tuesday outfit. Shop specially curated brooches, necklaces, purses, and more.
- Adelante: This boutique has everything you need for rodeo season! From hosting items to dresses, this is your one-stop shop for all things rodeo.
- Niche: This dynamic mother-daughter duo keeps their boutique stocked with the latest in-style designs for both men’s and women’s attire.
- Curio at Hotel Emma: Fancy a new pair of boots? This high-end luxury boutique housed inside Hotel Emma carries Fraulein Boot Company’s exclusive pair of men’s (The Otto) and women’s (The Emma) boots – perfect for any occasion.
Don’t miss: The Bi-Annual Sidewalk Sale is happening on Thursday, February 5, and Friday, February 6, and features exclusive deals from your favorite retailers like The Twig Book Shop, Niche, Adelante, and The Tiny Finch!
Put on your best dress, slide into your tried-and-true pair of boots, and make plans to visit Pearl this February. Whether you’re looking for outside stadium activities or family-friendly outings, cowboy culture at Pearl is not to be missed.
More Ways to Celebrate February at Pearl
While rodeo season takes center stage this month, Pearl has even more events lined up to make your February unforgettable. Whether you’re planning a romantic Valentine’s celebration, gathering with friends for Galentine’s Day, watching the big game, or looking for family-friendly activities, there’s something happening every week.
Big Game Sunday brings two distinct viewing experiences to Pearl on February 8. Sports fans can head to Stable Hall’s Big Game Watch Party for a free, all-ages viewing experience starting at 5:00 PM. Enjoy the championship game, halftime show, and drink specials in one of San Antonio’s premier entertainment venues – and feel free to bring your own food! Not a sports fan? No problem. Jue Let’s alternative watch party offers extended happy hour from 5:00 PM to 10:00 PM and free karaoke all night long. It’s the perfect spot to skip the football frenzy and sing your heart out instead.
Valentine’s Day celebrations span across Pearl’s beloved venues. Jazz, TX’s Valentine’s Day Residency offers an intimate evening of live music and romance, while Pullman Market’s Valentine’s Day event provides the perfect setting for a casual date night with craft beverages and artisan bites.
Galentine’s Day gets its own spotlight this year with multiple celebrations designed for gathering with your favorite people. The Galentine’s Bouquet and Bubbles Workshop at High Street Wine Co. combines flower arranging with sparkling wine for a creative, celebratory afternoon. Sternewirth’s Galentine’s Party and the Galentine’s Day celebration at Cape Bottle Room offer additional opportunities to toast friendship and make memories with your crew.
February Date Night Done Right at Cape Bottle Room
Looking for the perfect date night spot this February? Cape Bottle Room is serving up romance with its exclusive February specials. Try their new Apertif Crisp Platter – kettle chips piled high with charcuterie, artisan cheese, and cornichons, smothered with balsamic and hot honey. Pair it with their expertly curated wine flights for an unforgettable evening.
February Specials:
- The Romance Package – Two wine flights + Apertif Crisp Platter for $50
- After Dinner Indulgence – Wine flight + trio of chocolate truffles for $30
Whether it’s Valentine’s Day, Galentine’s with friends, or a well-deserved Tuesday treat, Cape Bottle Room’s cozy atmosphere and special pairings make it the go-to spot for wine lovers all month long. Learn more about Cape Bottle Room’s February offerings.
For movie lovers, don’t miss the rescheduled Movie Monday screening of “Casablanca” – the timeless romance is perfect for the season of love. These free outdoor screenings at Pearl Park remain one of San Antonio’s favorite February traditions.
Looking to stay active? ACTIVATE Boot Camp at 1100 Springs Plaza continues throughout the month, offering free outdoor fitness classes in one of Pearl’s most scenic settings. Get your workout in while enjoying the beautiful San Antonio weather.
Music fans should check out the monthly Jazz Brunch and Jazz Dinner for live performances in an intimate setting. Meanwhile, Concerts at Stable Hall bring nationally touring acts to Pearl’s premier live music venue throughout February.
Creative souls will love Maker Break Club at Niche, where you can learn new crafting skills while supporting local artisans. And foodies won’t want to miss Pullman Market’s Charity Chili Cook-Off, where you can sample some of San Antonio’s best chili recipes while supporting a good cause.
With rodeo festivities, Valentine’s celebrations, Big Game watch parties, live music, outdoor movies, fitness classes, and more, February at Pearl offers something for everyone. Mark your calendars, gather your friends and family, and discover why Pearl remains San Antonio’s favorite destination for year-round entertainment and community connection.
Planning your visit? Check out our complete events calendar and subscribe to our newsletter to stay updated on all the February happenings at Pearl.