GuadalaHARRY’s Bar & Grill in Historic Downtown Conroe is gearing up for a Halloween weekend packed with great music, lively energy, and a few surprises along the way. As one of downtown’s favorite destinations for food, drinks, and live entertainment, GuadalaHARRY’s continues to build its reputation at its new location on Simonton Street. This weekend’s lineup brings a mix of classic sound and crowd-friendly rhythm, starting Friday, October 31, with Cypress Union and wrapping up Saturday, November 1, with returning favorite Dan Ennis. Guests can expect two nights of live music that perfectly capture the spirit of the season.
Friday, October 31, 2025 – Cypress Union LIVE
This Halloween night, GuadalaHARRY’s transforms into the ultimate spot for a costumed celebration with live music from Cypress Union. The band, led by Randy and Tracy Wheeler, blends classic rock and country into a timeless, crowd-pleasing experience. Known for their engaging performances and familiar setlists, this duo creates an atmosphere that feels equal parts concert and community gathering.
Randy and Tracy’s chemistry on stage keeps the energy flowing, their harmonies pairing with confident guitar work and a touch of nostalgia. Their music bridges eras, connecting the old with the new in a way that brings audiences together. Listeners can expect a night of recognizable hits that span decades, the kind of songs that make you sing along before you even realize it.
As Halloween celebrations kick off across downtown, Cypress Union promises to bring a festive tone to the evening. Costumes, laughter, and plenty of dancing will fill the space as the band delivers a soundtrack tailor-made for the occasion. The crowd can look forward to a lively mix of rhythm and melody, whether they’re taking the stage area by storm or enjoying the view from their table.
GuadalaHARRY’s has always been about connection, and this Friday is no exception. Between great food, handcrafted cocktails, and the unmistakable energy of a live band, Halloween night in downtown Conroe will be one to remember.
Saturday, November 1, 2025 – Dan Ennis LIVE
Saturday brings a shift in pace with the return of Dan Ennis, whose acoustic performances have become a favorite among GuadalaHARRY’s regulars. Known for his smooth delivery and heartfelt songwriting, Dan creates an atmosphere that invites the audience to slow down and really listen. His sets often blend thoughtful originals with carefully chosen covers that complement his mellow yet engaging tone.
Dan’s performance style centers around authenticity. Each song is given space to breathe, and his voice carries a warmth that resonates throughout the room. It’s the kind of performance that brings people together through quiet moments and subtle emotion, making Saturday night a fitting follow-up to the high energy of Friday’s festivities.
Guests can expect a relaxed and inviting evening filled with great music, familiar faces, and the signature hospitality that defines GuadalaHARRY’s. Whether you’re winding down from a weekend of Halloween fun or simply in the mood for a night of good food and soulful music, Dan Ennis offers the perfect close to a weekend of sound and celebration.
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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