GuadalaHARRY’s Bar & Grill in Historic Downtown Conroe is keeping the fall energy alive with another weekend of live music that celebrates craft, connection, and timeless sound. Now several months into life at the new location on Simonton Street, the venue continues to fill its stage with artists who bring heart and authenticity to every note. This Friday, October 17, Dylan DuPont returns with his acoustic-driven performance and the same sincerity that’s earned him a loyal following in the area. Saturday, October 18, brings back Rick Sousley and Bob Bice, two seasoned performers whose chemistry and country roots create an easygoing night of music worth lingering for.
Friday, October 17 – Dylan DuPont LIVE
Dylan DuPont’s return to the GuadalaHARRY’s stage promises another evening of thoughtful songwriting and stripped-down sound. Known to audiences as “Mississippi Smile,” Dylan has built his reputation through years of performing in intimate venues where every lyric matters. His music blends plainspoken truth with the warmth of Southern storytelling, letting each song breathe on its own.
Listeners can expect a performance that feels both familiar and new. Dylan’s acoustic sets are deliberate in tone, weaving between soft ballads and rhythm-driven originals, with the occasional cover chosen for meaning rather than popularity. His songs often touch on memory, movement, and the quiet persistence of daily life, echoing influences like Guy Clark and Townes Van Zandt without losing his personal identity.
There’s an ease in the way Dylan performs. He doesn’t chase applause or fill space unnecessarily; instead, he creates it. The crowd settles in, the guitars hum low, and the words linger just long enough to make people pause between conversations. That balance of calm and craft defines his shows, making him a natural fit for an evening downtown where live music still feels genuine and grounded.
Saturday, October 18 – Rick Sousley and Bob Bice LIVE
Saturday brings a familiar duo to the spotlight with Rick Sousley and Bob Bice. Both men have long been fixtures of the Conroe music scene, known for their harmonies, humor, and the kind of stage chemistry that can only come from years of playing together. Their style draws heavily from traditional country, blending the storytelling roots of the genre with an easy confidence that puts every listener at ease.
Their setlist often includes songs that have become part of their musical identity, from Texas classics like “London Homesick Blues” to barroom favorites that always find the right mood. Rick and Bob perform with a comfortable rhythm, moving seamlessly between vocals and instrumentals that feel as natural as conversation. It’s not about reinventing the wheel, it’s about reminding people why they fell in love with live music in the first place.
There’s a certain nostalgia to their sound, a reminder of how simple arrangements and honest lyrics can carry a room. For longtime GuadalaHARRY’s guests, the connection runs deeper still; both Rick and Bob trace their history back to the venue’s earlier days on Lake Conroe, where they played as members of Raizin Cain, the first band ever to take that stage. Their return in the downtown space carries that legacy forward, uniting the past and present of a Conroe favorite.
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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