Another weekend of standout live music is coming to GuadalaHARRY’s Bar & Grill in Historic Downtown Conroe. With a strong lineup and a setting built for relaxed nights and good sound, this weekend features two artists who bring their own voice and energy to the stage. Jake Black leads off on Friday with a set full of heartfelt originals and thoughtful covers. On Saturday, Two Thirds returns with the kind of high-energy performance that always gets the room moving. From start to finish, the weekend is built around real talent, good timing, and the kind of atmosphere that defines GuadalaHARRY’s.

Friday, May 10 – Jake Black

A picture of Jake Black and Two Thirds Headline the Weekend at GuadalaHARRY’s at Guadalaharry's Bar & Grill

Jake Black is the kind of performer who doesn’t rely on theatrics or overproduction. His strength lies in how directly he connects with a crowd. Drawing from a mix of country, acoustic rock, and singer-songwriter influences, Jake delivers his set with intention. His originals are drawn from lived experience, shaped by honest lyrics and supported by a strong vocal presence.

He builds his shows with care, alternating tempo without disrupting the mood. Whether it’s a slower ballad or a more rhythm-driven track, the performance stays focused and consistent. His cover choices are never filler. Each one feels deliberate, shaped to match his tone rather than simply filling time. It’s that attention to pacing and tone that keeps the audience engaged.

Jake will be performing from 7:00 PM to 10:00 PM. For the best seats and a smooth start to the evening, guests are encouraged to arrive early, order from the kitchen, and enjoy a drink before the music begins.

Saturday, May 11 – Two Thirds

A picture of Jake Black and Two Thirds Headline the Weekend at GuadalaHARRY’s at Guadalaharry's Bar & Grill

Two Thirds is a duo with a sound built on rhythm, harmony, and timing. Their return to GuadalaHARRY’s brings a performance that leans into movement, crowd energy, and shared momentum. They don’t stick to one formula. Instead, they shift between upbeat hits and more grounded original work, adjusting to the room in real time.

What sets Two Thirds apart is how natural they sound together. Their vocal blend is clean, their instrumentation is tight, and their transitions are smooth. This is a group that plays to the crowd without losing their own identity in the process. Some songs are instantly familiar. Others carry new weight when delivered through their lens. No matter the tempo, they keep the night feeling unified and intentional.

They take the stage from 7:00 PM to 10:00 PM. These Saturday shows tend to draw early crowds, so reservations or early seating are recommended. The music will be steady, the atmosphere relaxed, and the setting ideal for a full evening downtown.

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.