Looking for a high-energy midweek escape? Join us for Music Singo at Lost Oak Cellars in the heart of downtown Boerne. Presented by Challenge Entertainment, this isn't your average bingo night—it’s a musical spin on the classic game that will have the whole tasting room singing along.

Event Details: Save the Date!

• When: Wednesday, May 13, 2026

• Time: 6:00 PM – 8:00 PM with Challenger Entertainment

• Admission: Free to attend—no reservations required!

What is Music Singo?

Instead of listening for a number, you’ll listen to clips of your favorite popular songs. If the song title is on your free SINGO card, mark it off! It’s fast-paced, interactive, and perfect for groups or a unique date night.

Sip and Win!

Make it a full Hill Country experience by enjoying everything our Boerne Tasting Room has to offer:

• Award-Winning Texas Wine: Sip on your favorites by the glass or bottle.

• Artisan Bites: Pair your wine with delicious charcuterie boards and light bites from our tasting room menu.

• Prizes: Winners of each round walk away with fantastic prizes.

• Historic Atmosphere: Relax in our beautiful building, recognized as a Texas Treasure, located just steps from Boerne’s Hill Country Mile.

Get ready to sip, sketch, and elevate your seasonal decor!

We are transforming our intimate Boerne Tasting Room into a vibrant creative hub for a beginner-friendly watercolor workshop. Guests will design and paint their very own custom 4x6 watercolor American flag.

This charming, whimsical design is perfectly timed, sized for easy framing and seasonal display through Memorial Day and the Fourth of July! No artistic experience is necessary, and all supplies are included.

Meet your canvas: Perfectly timed for patriotic display!

• Beginner-Friendly Watercolor: Downtown DIY will walk you through the process of creating this festive design. We provide all the supplies—paints, brushes, and the pre-sized watercolor paper—so you can focus on the fun.

• Whimsical Patriotic Art: You’ll leave with a unique, handmade masterpiece that is ready to be framed and shown off at your next summer gathering, backyard BBQ, or picnic.

• Intimate Boerne Setting: Our tasting room on the Hill Country Mile provides the perfect cozy, adventurous backdrop for this elegant creative process.

Sip while you Sketch: Red, White & Wine

What's a Crafts & Corks without the corks? Enjoy our full menu during the event, including:

• Texas Estates Wine Menu: Choose a glass (or a bottle to share!) of our award-winning reds, whites, and rosés.

• Gourmet Shareables: Pair your creative process with savory charcuterie boards and flatbreads from our updated food menu.

Event Details at a Glance

• Date: Thursday, May 14, 2026

• Time: 4:30 PM – 6:00 PM

• Feature: Crafts & Corks with Downtown DIY.

• Craft: Whimsical Watercolor American Flags.

• Admission: Open to the public; tickets required!

• 👉 Register Here (Link) (Space is limited!)

Are you ready for the perfect Thursday pour and paint? Grab your favorite people, explore our updated menu, and get ready for a creative night with Downtown DIY at Lost Oak Cellars! See you at the winery!

Thursdays in Boerne Just Got Better!

Half-Off Wine, Live Music, and Local Pop-Up Shopping Every Thursday.

Grab your girls and make Thursdays your new favorite night out! Join us at Lost Oak Cellars Boerne, TX, every Thursday from 6:00 PM – 9:00 PM for our exclusive Ladies Night. It’s the perfect retreat to unwind, socialize, and enjoy the best of the Hill Country.

50% Off Glasses of Wine & Live Entertainment

We’re celebrating our ladies with an incredible deal: enjoy 50% off all glasses of wine throughout the evening! Sip on your favorite Lost Oak varietals while listening to the soulful sounds of talented local musicians.

Shop Local: Featured Pop-Up Vendors

Each Ladies Night features unique finds from local creators.  It’s the perfect opportunity to shop local while you "wine down."

Event Snapshot & Details

• Event: Ladies Night (Recurring every Thursday)
• Time: 6:00 PM – 9:00 PM
• Location: Lost Oak Cellars
• Feature Deal: 50% Off Glasses of Wine
• Live Music: 6-9 pm with Dustin Endsley

No reservations are required—just bring your friends and get ready for a night of wine, music, and wonderful memories! We can’t wait to see you at the wine bar.

Get ready for the ultimate kick-off to your weekend!

 Meet your perfect glass: Sangria is here!

The star of the show (besides the music!) is our Sangria 

Meet the Music: Josh Jaccard (Classic Rock & Country)

We are thrilled to welcome back the Dallas-born vocalist and multi-instrumentalist, Josh Jaccard, to the Lost Oak stage. Raised in a musical family and performing professionally since age 18, Josh Jaccard is known all over Texas for delivering a high-energy, authentic, and seriously powerful performance.

Fronting classic rock bands, tribute acts (including an incredible Ultimate Bob Seger Tribute), and delivering standout solo shows, he highlights his impressive range, soulful delivery, and undeniable stage presence. Prepare for a set that is both nostalgic and refreshingly modern, made to be felt.

Explore More at Lost Oak Winery

While you enjoy your Sangria and the live performance, explore everything else our Burleson Tasting Room has to offer:

• Texas Estates Wine Menu: From premier estate-grown reds to refreshing, crisp whites.

• Tasting Room Cocktails: Try our unique wine-based cocktails or refreshing, handcrafted mocktails.

• Artisanal Charcuterie Boards: Pair your sips with savory plates and shareables from our gourmet food menu.

• Chips & Salsa: We’re bringing back the classic pairing! Enjoy complimentary chips and salsa with Sangria Carafe or Wine Bottle Purchase

Event Details at a Glance

• Date: Thursday, May 14, 2026

• Time: 6:00 PM – 9:00 PM

• Location: Lost Oak Winery, 8101 County Rd 802, Burleson, TX

• Feature: Sangria Thursday

• Live Music: Live Music: Josh Jaccard

• Admission: Open to the public; no reservations required!

Are you ready for the perfect Thursday pour? Grab your favorite people, explore our menu, and experience Sangria Thursday with Josh Jaccard at Lost Oak Winery! See you at the winery!

If you've never experienced a live Loteria night, you are in for a serious treat! The Loteria Lady is known for delivering a high-energy, laugh-out-loud, and seriously competitive twist on this traditional Mexican game of chance.

Meet the Fun: The Loteria Lady

We are thrilled to welcome back the incredible The Loteria Lady to the Lost Oak stage. If you’re looking for authentic, traditional Mexican Bingo (Loteria) with a serious side of live calling, music, and interactive entertainment, you are in the right place.

Prepare for a high-energy, and fun twist on a beloved game—a performance that is both nostalgic and refreshingly modern, made to be felt. The Loteria Lady delivers a full, unmissable experience, shifting seamlessly from dynamic calling to lively interaction, ensuring every round is packed with excitement.

Explore More at Lost Oak Winery

While you enjoy the Loteria and the relaxed, cozy atmosphere of our Tasting Room, take advantage of everything else our Burleson location has to offer:

• Texas Estates Wine Menu: From premier reds to refreshing whites.

• Tasting Room Cocktails: Try our unique wine-based cocktails or refreshing, handcrafted mocktails.

• Artisanal Charcuterie Boards: Pair your sips with savory plates and shareables from our gourmet menu.

Event Details at a Glance

• Date: Friday, May 15, 2026

• Time: 7:00 PM – 9:00 PM

• Location: Lost Oak Winery, 8101 County Rd 802, Burleson, TX

• Entertainment: The Loteria Lady

• Admission: Open to the public; no reservations required!

Are you ready for the perfect Friday pour? Grab your favorite people, explore our menu, and experience Friday Night Loteria with The Loteria Lady at Lost Oak Winery! See you at the winery!

Get ready for a laid-back, delicious Saturday in Boerne!

We are transforming our Boerne Tasting Room into a festive, adventurous mudbug haven from 12:00 PM until we run out!

Crawfish Boil Details

We are pulling out all the stops for a seriously satisfying afternoon:

• The Boil: Perfectly seasoned, fresh crawfish served straight from the pot for just $8 per pound. Each pound comes complete with potatoes and corn.

• Serving Until Gone: The crawfish boil kicks off at noon and will be served until it’s gone. Come early to grab your share—this is not a "call ahead" order!

• Laid-Back Vibes: Gather your friends, find a spot, and enjoy a seriously casual, fun-filled day at the winery.

Meet the Sips: Wine & Pours

What's a crawfish boil without the perfect pour? Enjoy everything our Boerne Tasting Room has to offer:

• Texas Estates Wine Menu: Choose a glass (or a bottle to share!) of our award-winning reds, white blends, and rosés. Be sure to try our Blanc Du Bois—it’s the classic pairing!

• Gourmet Shareables: Pair your boil with artisanal charcuterie boards and tasty bites from our updated food menu.

Event Details at a Glance

• Date: Saturday, May 16, 2026

• Time: 12:00 PM – Until Gone

• Location: Lost Oak Cellars, 111 Rosewood Ave, Boerne, TX

• Entertainment: TBA! We are booking dynamic live music to match the energy.

• Admission: Open to the public; no reservations required!

Are you ready for the perfect Saturday pour? Grab your favorite people, don your favorite adventurous hat, and experience the Crawfish Boil at Lost Oak Cellars! See you at the Mile!

Looking for the perfect Saturday night in Burleson?

Get ready for an energetic, fresh, and grit-infused evening of Traditional Country, Texas Country, and original songs from this talented singer-songwriter and performer. Grab your friends, explore our updated menu, and experience a lively evening where great taste meets authentic Texas sounds, all under the beautiful Burleson sky.

Meet the Music: Jack Mason

We are thrilled to welcome Jack Mason to the Lost Oak stage. Known for delivering great variety and engaging live shows, Jack Mason connects with his audience through powerful vocals, skillful songwriting, and a dynamic stage presence.

Prepare for a set that seamlessly shifts between timeless traditional country covers, beloved Texas Country hits, and Jack Mason’s own original, grit-infused tracks—a performance that is both nostalgic and refreshingly modern, made to be felt.

Explore More at Lost Oak Winery

While you enjoy the concert on the lawn and the relaxed, adventurous backdrop of our winery, take advantage of everything else our Burleson location has to offer:

• Texas Estates Wine Menu: From premier estate-grown reds to refreshing white blends.

• Tasting Room Cocktails: Try our unique wine-based cocktails or refreshing, handcrafted mocktails.

• Artisanal Charcuterie Boards: Pair your sips with savory plates and shareables from our gourmet menu.

• Chips & Salsa: We’re bringing back the classic pairing! Enjoy complimentary chips and salsa with Sangria Carafe or Wine Bottle Purchase

Event Details at a Glance

• Date: Saturday, May 16, 2026

• Time: 6:00 PM – 9:00 PM

• Location: Lost Oak Winery, 8101 County Rd 802, Burleson, TX

• Music: Jack Mason (Country & Texas Country).
• Admission: Open to the public; no reservations required!

Are you ready for the perfect Saturday pour? Grab your favorite people, explore our menu, and experience the Concert on the Lawn with Jack Mason at Lost Oak Winery! See you at the winery!