As fall evenings settle over Historic Downtown Conroe, GuadalaHARRY’s Bar & Grill continues its strong run of live music weekends at our new location on Simonton Street. The stage has quickly become a gathering place for both locals and visitors who crave good food, friendly faces, and memorable performances. This weekend offers two nights that showcase distinct sides of Texas music. On Friday, October 24, 2025, Lakeside Avenue returns with their engaging acoustic sound and signature mix of styles. Then on Saturday, October 25, Texas Roughcut Band makes their first appearance at GuadalaHARRY’s, bringing a dose of classic country swagger with a touch of Southern rock.
Friday, October 24, 2025 – Lakeside Avenue LIVE
Lakeside Avenue has built a loyal following through their ability to connect with audiences and reinterpret familiar tunes with warmth and originality. Featuring JR Pena and Kyle Schmidt, this acoustic duo combines tight harmonies with a natural ease that makes every performance feel personal. Their style crosses boundaries, weaving together elements of pop, rock, and country into a sound that feels both refined and relaxed.
Audiences can expect an evening that moves fluidly from upbeat covers to heartfelt ballads. Lakeside Avenue’s setlist always keeps listeners guessing, shifting from singalong favorites to stripped-down originals that showcase their musicianship. JR’s smooth vocals blend perfectly with Kyle’s rhythmic guitar work, creating a balanced and inviting sound that fills the room without ever overpowering it.
Their performances are marked by authenticity and charm. The duo interacts effortlessly with the crowd, often taking requests or sharing stories between songs. That chemistry makes their shows feel less like a concert and more like a shared moment between friends. Whether you’re joining us for dinner, drinks, or just the music, Friday night with Lakeside Avenue promises a perfect start to the weekend in downtown Conroe.
Saturday, October 25, 2025 – Texas Roughcut Band LIVE
Saturday night welcomes the debut of the Texas Roughcut Band, a group that carries the spirit of true classic country with a touch of grit. Based right here in Texas, they bring an authentic sound steeped in storytelling and tradition. Their music draws from legends of the genre, paying tribute to the likes of George Strait, Merle Haggard, and Alan Jackson, while adding their own twist of classic rock influence that keeps things lively and unpredictable.
Texas Roughcut Band’s shows are known for their tight rhythm section, soulful vocals, and the kind of guitar work that gets toes tapping from the first chord. Expect an energetic performance that balances heartfelt ballads with honky-tonk drive and blues-inspired grooves. Their mix of classic hits and originals captures the heart of country music, with songs about love, life, and the road, all delivered with sincerity and skill.
As a new addition to the GuadalaHARRY’s lineup, this band promises to bring a fresh flavor to our Saturday night stage. Their reputation for keeping dance floors full and spirits high precedes them, and their arrival marks another milestone in our growing roster of regional talent. With the Texas Roughcut Band, you’ll find yourself singing along before you even realize it.
Venue Information
GuadalaHARRY’S Bar & Grill – Music Patio
12947 Lake Conroe Hills Drive
Willis, Texas 77318
+1 (936) 701-5168
Every weekend, GuadalaHARRY’s Bar & Grill invites local bands and up-and-coming artists to perform live on our music patio. Enjoy fresh seafood, steak, Tex-Mex, and Cajun cuisine, hand-crafted cocktails, beautiful sunset views, and live entertainment on Lake Conroe every Friday and Saturday from 7:00 pm – 10:00 pm.
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