7 Best Ways to Kick Off Summer in San Antonio This Memorial Day Weekend

Tenfold Rooftop Bar at Kimpton Santo San Antonio – Riverwalk. Photo: Kimpton Santo San Antonio, used with permission.

San Antonio Memorial Day Weekend Guide: Rooftop DJs, Pool Parties, and New Hotspots

With Memorial Day Weekend marking the unofficial start of summer, San Antonio is buzzing with energy. Whether you are a local planning a staycation or a visitor exploring the Alamo City, top local establishments are rolling out the red carpet. From rooftop DJs and curated cocktail tastings to resort-style pool days and exciting new venue launches, here is how you can celebrate the long weekend in style. (La Panadería, Miles, The Newstand Coffee & Sandwiches, Kimpton Santo San Antonio, Plaza San Antonio Hotel & Spa, Pearl, The Gunter Hotel, 2026)

Bakery Lorraine, Otto’s Ice House, and Freight Fried Chicken will be open for business on Memorial Day for guests looking for places to dine with loved ones. Corinne San Antonio located inside Plaza San Antonio Hotel & Spa will also be offering its brunch menu from 7a.m. – 3p.m. on Memorial Day.

🍹 Sips & Snacks

La Panadería

What: Seasonal Drinks Launch & Memorial Day Brunch When: Launching Friday, May 22 & Friday, May 29 (Available all summer)

Just in time for the warm weather, La Panadería is introducing a limited-time lineup of seasonal beverages blending citrus, spice, and refreshing summer flavors. They will also be open on Memorial Day hosting a spectacular brunch.

  • Launching May 22:
    • La Panadería Mont Blanc: Vanilla-orange cold brew topped with orange cold foam and fresh orange zest.
    • Matcha Mont Blanc: An iced matcha latte topped with orange cold foam and orange zest.
  • Launching May 29:
    • Spicy Sparkling Pomegranate Lemonade: A refreshing mix of jalapeño simple syrup, lemonade, and pomegranate syrup topped with sparkling water. Bonus: This mocktail can be made alcoholic by adding tequila.

The Newstand Coffee & Sandwiches

What: National Wine Day Celebration When: Monday, May 25

Celebrate National Wine Day with a specially curated wine experience helmed by Advanced Sommelier & Beverage Director Austin Tabbone. The Newstand’s menu breaks wine down into approachable, fun categories like Bubbles and Sweets, Red and Berry Fruited, Weighty and Textured, and The Weird Reds. Pair your glass with refined light bites like a cheese board, house-made Focaccia, or stuffed dates for the perfect date night or girls’ night out.

🏖️ Poolside Vibes & Rooftop Parties

Kimpton Santo San Antonio – Riverwalk

What: Tenfold Spin & Swim: Lover’s Rhythm Edition When: Sunday, May 24 | 3:00 PM – 8:00 PM

Summer returns with a sunset state of mind at Kimpton Santo’s skyline celebration. Hosted atop the Tenfold Rooftop Bar in collaboration with For Lovers Only and Release The Rhythm, guests can enjoy panoramic views, poolside energy, and flowing Aperol cocktails.

  • The Beats: Soundtrack provided from day to dusk by DJ Cura, DJ Natvillain, DJ OmgNini, and DJ Retrostatic.
  • Admission: Tenfold access is free and open to the public (space is limited; reservations via OpenTable are highly encouraged).
  • Pool Access: Non-hotel guests can access the pool via ResortPass. For May 24, Day Passes are $80 and private cabanas are available for $300.

Plaza San Antonio Hotel & Spa

What: Summer Reset: Garden + Pool Kickoff When: Sunday, May 24 | 1:00 PM – 5:00 PM

Join Plaza San Antonio poolside at the Anaqua Garden Bar for a sun-drenched sanctuary experience featuring live music from DJ Mars and curated cocktail tastings by High Desert Vodka.

  • Featured Cocktails:
    • Desert Bloom: High Desert Vodka, lemon, prickly pear, agave, elderflower liqueur, soda.
    • Anaqua Crush: High Desert Vodka, cucumber juice, lemon, agave, yuzu.
    • Desert Water: High Desert Vodka, lemon, prickly pear, lime, soda.
  • Admission: Access to Anaqua Garden Bar is free and open to the public (space is limited; reservations via OpenTable encouraged).
  • Pool Access: Non-hotel guests can access the adjacent pool via ResortPass. For May 24, Day Passes are $40 and cabanas start at $100.

💡 Locals’ Tip: Summer Kick-off with ResortPass Can’t make it this Sunday? Both Kimpton Santo and Plaza San Antonio offer ResortPass access all summer long.

  • Kimpton Santo: Features the tallest luxury open-air rooftop pool in the city. Standard summer day passes start at $55; cabanas start at $100. Book Here
  • Plaza San Antonio: Enjoy a lush garden oasis, spa, and pool nestled between Downtown and Southtown. Standard summer day passes start at $30; cabanas start at $50. Book Here

🎶 Live Music & Festivals

Pearl Fest

What: A District-Wide Live Music Festival When: Saturday, May 23 | Starting at 11:00 AM Where: Pearl Parking Lot (under Highway 281), 303 Pearl Pkwy

Pearl Fest is bringing over 15 bands to the heart of the Pearl district, headlined by the legendary Los Lonely Boys.

  • 11:00 AM (Free): The music kicks off during the weekly Farmers Market with a free, open-to-the-public stage at Pearl Park.
  • 4:00 PM (Ticketed): Doors open for the main stage under the 281 highway. Day-of tickets are $35 (available in person at the gate).
  • District-Wide Free Showtimes:
    • Sternewirth (Hotel Emma): The Pertnears (2 PM – 5 PM), Diego Martinez (6 PM – 9 PM), DJ Cura (10 PM – 1 AM).
    • Yellow Rose by Kendra Scott: Live music from 3 PM – 5 PM.
    • Pullman Market (Karnes Patio): Live DJ from 3 PM – 10 PM.
    • Otto’s Ice House: Josh Baca and The Hot Tamales (6 PM – 10 PM).
    • Stable Hall: Reverend Horton Heat at 8 PM.
    • After-Parties (10 PM): Keep the night going at Cape Bottle Room and Jue Let.

🏨 Staycations & New Openings

The Gunter Hotel

What: “Where Summer Comes Alive” Staycation Package When: Bookable now through August 31

Looking to extend your holiday weekend? The Gunter Hotel in downtown San Antonio is debuting a brand-new summer travel package.

  • The Deal: Book two nights and get a complimentary third night.
  • Perks: Includes discounted valet parking ($39/night) and access to the hotel’s unique Vinyl Library Experience, where you can check out up to three vinyl records to enjoy right in your room.
  • How to Book: Head to the “Offers” page on the Gunter Hotel Website.

Miles

What: Grand Opening / Memorial Day Weekend Celebration When: Soft opening Friday, May 22 Where: 1170 E. Commerce St.

The East Commerce corridor has a brand new rhythm. Say hello to Miles, a high-energy bistro and cocktail-forward neighborhood bar from Dreamers & Doers Hospitality Group. Inspired by the legendary jazz innovator Miles Davis, the space is anchored by an expansive 360-degree central bar designed for late-night conversations and sharing elevated small plates.

  • Hours: Post-holiday weekend, Miles will be open weekly from Wednesday through Monday, 5:00 PM to midnight (extended until 1:00 AM on Fridays and Saturdays).
  • Reservations: Secure your spot now via Resy.

Cozy Up Sundays at Rosario’s & More Holiday Events Happening in San Antonio

Miracle on Arciniega Pop-Up at Anaqua Garden Bar. Photo: Plaza San Antonio Hotel & Spa + Tay Simmons, used with permission.

Cozy Up Sundays Return to Southtown Rooftop Bar at Rosario’s 🌆

Rosario’s ComidaMex & Bar announces the return of Cozy Up Sundays at its Southtown Rooftop Bar, running now through January, every Sunday from 2 p.m. to 9 p.m.

Each Sunday, guests are invited to embrace the brisk winter air while enjoying handcrafted cocktails and bites for just $8, all paired with sweeping panoramic views of San Antonio’s skyline. Patrons are encouraged to gather loved ones and cozy up under Rosario’s signature pink blankets for the ultimate rooftop experience.

To ensure comfort during San Antonio’s unpredictable winter weather, space heaters are placed throughout the rooftop bar. On colder evenings, the bar’s enclosed space offers a warm and inviting retreat without sacrificing the atmosphere.

Located in the heart of San Antonio, Rosario’s provides a welcoming space where guests can fully immerse themselves in the city’s rich roots and vibrant culture, making it the perfect Sunday destination.(Rosario’s ComidaMex & Bar, 2025)

📍 Address
722 S. St. Mary’s St.
San Antonio, TX


More Holiday Dining & Events in San Antonio 🎄

Looking for more ways to celebrate the holidays this month? Here are some standout experiences happening around the city:


Ambler Texas Kitchen + Cocktails

Holiday Dinner on the River Walk
📅 December 24 & 25 | ⏰ 5–8 p.m.

Celebrate Christmas Eve and Christmas Day with a festive holiday menu featuring prime rib, roasted turkey, seared salmon, and decadent desserts. (Ambler Texas Kitchen + Cocktails, 2025)

📍 Address
306 W. Market St.
San Antonio, TX 78205

🔗 Booking link


Plaza San Antonio Hotel & Spa

Miracle on Arciniega Pop-Up at Anaqua Garden Bar
📅 Open now – Sunday, December 28

Anaqua Garden Bar transforms into a winter wonderland with twinkling lights, seasonal décor, cheerful music, and a limited-time holiday craft cocktail menu served in themed mugs. (Anaqua Garden Bar, 2025)

Guests can also enjoy:

  • Cozy s’mores activations
  • A tunnel of lights
  • Hourly snow showers

Now in its second year, Miracle on Arciniega serves as a festive bridge between Downtown and Southtown, making it an ideal gathering spot for locals and visitors alike.

📍 Address
555 S. Alamo St.
San Antonio, TX 78205

🔗 Reservations recommended


The Tenth Noel: A Rooftop Christmas Affair

Tenfold Rooftop
📅 Friday, December 19 – Thursday, December 25

Celebrate the season from above the city at Tenfold Rooftop’s weeklong Christmas pop-up featuring festive cocktails, elevated holiday bites, and stunning skyline views. (Tenfold Rooftop, 2025)

📍 Address
431 S. Alamo St.
San Antonio, TX 78205

🔗 Reserve via OpenTable


Gunter Hotel

Jots Signature Christmas Prime Rib
📅 Monday, December 22 – Friday, December 26
💲 $29 per person | Regular menu also available

Jots Restaurant is serving a comforting holiday favorite: Signature Prime Rib with rosemary au jus, fresh horseradish cream, and smashed potatoes—perfect for a classic Christmas meal downtown. (The Gunter Hotel, 2025)

📍 Address
311 N. St. Mary’s St.
San Antonio, TX 78205

🔗 Reserve via OpenTable


Live Music at Bar 414 & Vinyl Library

📅 Every Thursday–Saturday | ⏰ 8 p.m.

The Gunter Hotel’s newest speakeasy, Bar 414, hosts live music every Thursday through Saturday in December (excluding Christmas Day). Meanwhile, the Vinyl Library sets the mood in the lobby with its “Spin the Season” holiday vinyl curation.

📍 Address
205 E. Houston St.
San Antonio, TX 78205


Holiday Family Meal Options 🥘

Freight Fried Chicken

Family Meal Packs
💲 $50 per pack

Family meals include 8 or 10 chicken tenders and a choice of three shareable sides, such as:

  • Mac N Cheese
  • Seasoned Fries
  • Slaw
  • Loaded Potato Salad

Optional add-ons include biscuits, hot honey drizzle, jalapeños, and more. (Freight Fried Chicken, 2025)

📍 Address
312 Pearl Pkwy, Building 6
San Antonio, TX 78215

🔗 Order here


The Jerk Shack

Family Meal Packs
💲 $70–$75 per pack

Family meals include 14 pieces of chicken (Fried, Jerk +$5, or Mixed +$3), three shareable sides, and an order of plantains. (The Jerk Shack, 2025)

Side options include:

  • Mac N Cheese
  • Masala Fries
  • Pineapple Slaw
  • Potato Salad

Dine-In Holiday Family Package
📅 Now – Wednesday, December 31
💲 $120 | Feeds 4–6 people

Guests can choose two appetizers, three entrées, and three sides, making holiday dining easy during the busiest time of year.

📍 Address
10234 TX-151, Suite 103
San Antonio, TX 78251

🔗 Order here

Freight Fried Chicken opens at Pearl this Saturday

Freight Fried Chicken will be located in the food hall at the Bottling Department. Photo: A.J. Creative, used with permission.

Award-winning chef Nicola Blaque will open her latest concept, Freight Fried Chicken, at the Food Hall at Bottling Department at Pearl on Saturday, January 13, 2024. Chef Blaque, whose fried chicken recipe has caught the attention of Eater, San Antonio Express-News and others on numerous occasions, created Freight Fried Chicken as a homage to the rich culinary history and traditions shared amongst Black Americans. Freight Fried Chicken draws its inspiration from black women in post Civil War America that sold fried chicken to rail passengers traveling through Gordonsville, VA. The women became known as Waiter Carriers and their chicken recipes would attract travelers who would go out of their way just to try the famous chicken. The sale of fried chicken allowed formerly enslaved women to support their households and create racial progress in a time fraught with dissension. (Freight Fried Chicken, 2024)

Freight Fried Chicken will use a dry batter for its chicken, which is similar in style to what was served by the Waiter Carriers. The chicken will also be served with biscuits, just like it was served on those trains so many years ago. Guests can also expect to see fried chicken tenders, a fried chicken sandwich, biscuits, mac ‘n’ cheese, seasoned fries, a vegetarian sandwich option, and more on the menu. Freight Fried Chicken’s bone-in chicken is halal and all of its batter is gluten free.

Opening date: Saturday, January 13, 2024
Hours will be 10a.m. to 9p.m. Sunday – Thursday and 10a.m. to 10p.m. Friday and Saturday

The Food Hall at Bottling Department
312 Pearl Pkwy Building 6
San Antonio, TX 78215

Lattoia Massey, known professionally as Chef Nicola Blaque, is a restaurateur and chef based in San Antonio, Texas. Chef Blaque is the executive chef and owner of the Jerk Shack, a Jamaican-inspired restaurant in San Antonio. The restaurant offers fare like jerk chicken, braised oxtail and quickly became a staple after opening in 2018. She also opened Mi Roti, a Caribbean concept at the popular Pearl district in San Antonio, in the summer of 2020, which is now being redeveloped into her latest concept, Freight Fried Chicken.

In addition to running successful concepts that have been recognized by GQ, Eater and more, Chef Blaque is an Army Veteran, a graduate of The Culinary Institute of America in San Antonio, a private chef for members in the NBA, a wife and a mom. Having been born and raised in Jamaica until she was five years old, Chef Blaque is passionate about introducing people to the flavors of the Caribbean. Though she’ll be the first to tell you that the dishes she’s serving up aren’t always traditional Jamaican dishes, she’s passionate about infusing those flavors into cuisine her patrons know and love.

Pearl is a dynamic neighborhood built around the historic Pearl Brewery, located just north of downtown San Antonio on the banks of the San Antonio River. Pearl is home to architecturally significant buildings like the brewhouse and stable—both built in 1894—and numerous plazas. Today, Pearl is home to dozens of unique culinary concepts, one-of-a-kind retail, weekend markets, residential communities, innovative office tenants, the San Antonio campus of the Culinary Institute of America, and the award-winning Hotel Emma. Pearl is a vibrant district where the community gathers to play, work, and live; it is a place where things are made and celebrated with purpose and sincerity.

Courtesy photo, used with permission.
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Freight Fried Chicken opening date