Saturday night at Shiloh & Gaines with The Grateful Family Band. That room gets a good crowd on weekends, and a 9pm start means you can grab dinner first and still catch the whole thing. Trivia kicks off around 7pm on Wednesdays at this Hendersonville Road spot, where the dive bar vibe and full cocktail program make it easy to settle in for the long haul. Grab a table inside or hit the patio if the weather cooperates, and stick around past 8pm when it goes 21+ only.