Chapelton Wine School Program
Chapelton Wine School Program Viticulture: Vine to Grape Dates: March-July 2025 Winemaking: Grape to Bottle Dates: July-November 2025 Pricing Track – $250 Both Tracks – $450 Wine Club Members – 10% Off Discover the world of viticulture and winemaking at Chapelton Wine School, where you’ll embark on an immersive, hands-on journey. Our program offers unique vineyard experiences and…
Boerne Market Days – May 10
Come visit Lost Oak Cellar’s during the Boerne Market Days for something to sip while you shop. At Boerne Market Days, spend a day browsing the market and visiting the many downtown boutiques, galleries and restaurants for a unique hill country experience. 100 N Main Street Boerne, TX 78006
Aimee Bobruk Live at WSCW May 10
Aimee Bobruk, a singer/guitarist who has been writing and performing for over 10 years. Raised in Huntsville, TX, she is currently based in Copenhagen, Denmark. Bobruk’s songs are genuine and original. She doesn’t pattern herself after any other singer-songwriter but instead chooses to make her own trail.
The McGrath Project (duo) – May 10
Concert on the Lawn time at Lost Oak Winery with the The McGrath Project duo! Enjoy charcuterie & paninis to complement your favorite award-winning Texas wine! Free to attend, no reservation required. No outside alcohol permitted per TABC regulations.
Live at Lost Oak with Jaime Varela – May 10
Enjoy an evening of live music with Jaime Varela! Enjoy award-winning Texas wine while snacking on charcuterie. Free to attend, no reservation required. See you there! ~ cheers!
Mimosa Mothers Day – May 11
Join us for a Mother’s Day celebration at Lost Oak Cellars! Enjoy live music by John David. Treat Mom to a mimosa and a piece of jewelry from Permanent Jewelry of Texas.
Market in the Vines – May 11
New for 2025 – Market in the Vines! A traditional farmers market held on the lawn of the beautiful Lost Oak Winery hosted by MomBoss Sip & Shop! Now accepting vendors – please message MomBoss at facebook.com/MomBossSipNShop or email Mombosssipnshop@gmail.com
Music Bingo Boerne – May 14
Come join us for a fun-filled evening of Music Bingo with Challenge Entertainment! Listen and sing along to your favorite songs, mark off the songs on your card, and yell BINGO to win great prizes! Free to attend and free to participate.
Lost Oak Live with Julia Rose – May 15
Enjoy an evening of live music with Julia Rose! Enjoy award-winning Texas wine while snacking on charcuterie. Free to attend, no reservation required.
Lost Oak Live Jazz Night with Tiny Jazz – May 16
An evening of live jazz with Tiny Jazz! Enjoy award-winning Texas wine while snacking on charcuterie. Free to attend, no reservation required.
Crawfish Boil – May 17
We are having a Crawfish Boil! We will start serving at 2 pm and go until we run out! Come get some!
JP Lee Live at WSCW May 17
JP Lee is a guitar-slinging artist and songwriter with a big following in Houston. He has two Grammy nominations and over a dozen Billboard charted songs. In addition to his solo career, he writes and performs all over the Houston area with new and established artists.
Lost Oak Live with Jeremy Parsons – May 17
An evening of live music with Jeremy Parsons! Enjoy award-winning Texas wine while snacking on charcuterie. Free to attend, no reservation required.
Byron Haynie Live at WSCW May 18
Byron is a Texas-based, country/Americana guitarist, vocalist, and songwriter. Byron is an award-winning performer with an extensive playlist, a variety of genre and songs including country, current hits, oldies, blues, southern rock and more!
Paint & Sip: Red, Wine and Blue – May 21
Kick off your Memorial Day celebrations with a creative twist at Lost Oak Winery! Join us for a festive Red, Wine, & Blue Paint & Sip night, where you’ll paint a patriotic masterpiece perfect for the holiday weekend. No experience needed — just bring your creativity, and we’ll handle the rest. Sip on delicious wine…
Ryan Pinnick Live at WSCW May 24
Ryan is a full time solo acoustic performer in the Houston area who can bring can life to any type of special occasion. He plays a wide variety of hits from the 70's , 80's and 90's and a multitude of genres including : Classic Rock, Pop, Easy Listening , Top 40, Alternative and... three…
Robert Cline, Jr. Live at WSCW May 31
Robert Cline, Jr. presents an acoustic mix of folk, country and alt country classics. His most recent album, Troubadour Songs, Vol. 1, captures the spirit of the people and places that paved the road to a life of writing, touring & performing with true legends of the craft.
Paella Night And Tempranillo Release Party
Join us at Driftwood Estate Winery on Saturday, May 31st from 6–8 PM for an evening of bold flavors, fine wine, and live music as we celebrate the release of our newest Tempranillo vintage. Enjoy your choice of seafood or meat paella, a complimentary glass of Tempranillo, and sample our newest release while soaking in…
James Zimmerman Live at WSCW June 1
James Zimmerman's signature style is soothing piano and rich vocals that provide the perfect backdrop for a pleasant afternoon at the winery. So come, relax and enjoy the ranch, the wine, and the beauty of the forest.
Dueling Pianos – June 6
Dueling Pianos is back! Join us for this one-of-a-kind interactive Dueling Pianos show with the Eighty Eights performing live popular songs from the classics to today’s hits on the Lost Oak Winery lawn. Boomers Kitchen food truck will be on-site for dinner. This show is Ages 21+ only. Get your tickets at lostoakwinery.com/product/dueling-pianos/
Lone Star Speakeasy Special – Friday June 6
Lone Star Speakeasy Special. Return to the Roaring 20s onboard Grapevine Vintage Railroad this summer with the Lonestar Speakeasy Special! Friday, June 6, 2025, at 7:25 p.m.
Tale of Texas Oak Tasting – June 7
Building on its foundation of innovation, Bending Branch Winery will release three new wines aged with Texas white oak at this exclusive tasting event. The first winery to ever use Texas white oak as part of its wine aging program, Bending Branch selected this new oak profile to add another layer of Texas terroir to its wines.…
Justin Cole Live at WSCW June 7
Justin Cole has been writing songs since 2000. He plays a wide variety of country music as well as rock.
Todd Roth Live at WSCW June 8
Please welcome Todd Roth back to the WSCW stage! Todd plays swampy blues straight from the soul. "Delta, Piedmont, Hill Country and Cotton Patch Soul, brace yourselves!"
Succulent Wreath Workshop – June 11
Join Ashleigh from Crazy Plant Lovee for a fun DIY living succulent wreath workshop! Make a beautiful wreath with a mix of succulents and decor. The workshop includes: 12-inch grapevine wreath with twine to hang, live succulents, preserved moss, and all other materials needed to decorate and put them together! Space is limited -…
Kyle Mathis Live at WSCW June 14
Kyle has a unique take on originals from bands from the 80s to today. His rapport with the audience makes him very popular with the WSCW crowd!
Kayleigh Mathews Live at WSCW June 15
Kayleigh is a country music singer-songwriter and Nashville recording artist. She performs at venues throughout the US promoting her newest EP “Turn Out The Lights.” It is a perfect example of her Honky Tonk roots, powerful vocals, and incredible song writing abilities that can only be found in her original music.
Jackson James Band Live at WSCW June 21
Jackson James is a bluegrass and country artist who covers a multitude of songs from different genres and gives them his own twist. He includes sounds across all generations of bluegrass and country, creating a unique performance that everyone can enjoy.
Guthrie Jones Live at WSCW June 22
Guthrie Jones is an eclectic, acoustic two-piece band whose music serves up a big helping of natural, home-grown Texas originals with a side of classic covers flavored with blues, country, folk, gospel, reggae and rock. Danny and Joni's roots in arts and education are reflected in their performance of music that "goes somewhere" in tune,…
Game Night – Let’s Play Bingo! June 27
What goes with wine? Bingo! Join us for a fun and informal after-hours event drinking wine and playing bingo. Your ticket includes a hearty hot and cold appetizer buffet and two bingo play cards. Doors will be open at 6:00 p.m. and bingo starts at 7:00 p.m. No tickets sold at the door; advance purchase…