GuadalaHARRY’s Bar & Grill in Historic Downtown Conroe keeps the momentum going with another weekend of standout performances. With summer in full swing and the new location drawing strong crowds, the stage is set for two nights of music that highlight both storytelling and tradition. On Friday, June 27, Dylan DuPont returns with his thoughtful acoustic set and well-worn guitar. Saturday features Rick and Bob, known for their rootsy country sound and familiar presence. These performances offer lyrical depth, solid musicianship, and a great way to enjoy live music downtown.
Friday, June 27 – Dylan DuPont LIVE
Dylan DuPont brings a sincere and stripped-down acoustic performance built around clean melodies and lyrics that carry weight. Nicknamed “Mississippi Smile,” Dylan developed his sound through years of playing small venues and connecting directly with audiences. His music is shaped by Southern storytelling, personal experiences, and an easy stage presence that resonates with listeners.
Each song in his set holds its own purpose. The tone is calm but never dull, drawing from the influence of artists like Guy Clark while maintaining his own voice. His delivery is steady, his guitar work polished, and his pacing intentional. He creates a relaxed atmosphere that allows the room to settle in and listen, without forcing attention.
Dylan’s shows typically include original songs and select covers that match his style. He avoids playing for trend or recognition and focuses instead on meaning and mood. For those who enjoy songs that speak plainly and honestly, his performance provides a quiet strength that stays with you long after the set ends.
Saturday, June 28 – Rick and Bob LIVE
Rick and Bob return to the stage with their signature blend of traditional country and longtime performance chemistry. Both artists have a deep history with the local music scene, including their time with Raizin Cain, the first band to perform at the original GuadalaHARRY’s on Lake Conroe. Today, they continue that legacy in downtown Conroe with a sound built on tight harmonies, classic tunes, and unforced charm.
Their show leans into familiar country standards like “London Homesick Blues” and “Copperhead Road,” blending skilled vocals with straightforward instrumentation. Their connection with the audience is natural and steady. The focus remains on strong songs and honest delivery, without relying on flash or gimmicks.
Rick and Bob offer a reminder that some music styles remain timeless. The evening will be relaxed, engaging, and full of moments that resonate with longtime country fans. For those who appreciate down-to-earth performances rooted in experience, this is a night worth showing up for.
Venue Information
GuadalaHARRY’S Bar & Grill – Historic Downtown Conroe
219 Simonton Street
Conroe, TX 77301
+1 (936) 701-5168
GuadalaHARRY’s Bar & Grill offers live music, fresh seafood, steak, Tex-Mex, Cajun dishes, and hand-crafted cocktails in the heart of Historic Downtown Conroe. Every weekend, guests enjoy a welcoming atmosphere, outstanding service, and performances that showcase some of the best talent in the region.
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