Requiem for a Jail Break: The Festival's Final-ish Season

Wind through the walls of the Old City Jail to discover art installations, local eats, and live musical acts Beach Tiger, ET Anderson, Hermit's Victory, and headliner Brave Baby.



I had the pleasure of attending Jail Break last year, despite being there to work, so I jumped on the opportunity to attend this year. I suppose, because I’m writing about it, you could call it work, but the event does a great job in minimizing any negative connotations to that word, “work.” You might even say it kind of flipped the script on the word itself, because any work done within those walls is sort of cheating since I had so much fun. Maybe even a little too much fun —thanks beer!







The festival commenced on Sunday, Oct. 15th after a small rain delay the day before – most likely to assure the live dance and music acts were able to perform to their fullest, and safely at that.


The festival, coined on the website as “an all-encompassing music and arts festival” has graced Charleston for over 9 seasons, each time impressing festival-goers with all sorts of art, poetry, installations, dance, comedy, and live music. This past event marks the “end” of the festival as we’ve seen it for many years, but it may come back in some iteration. With the theme “Requiem,” this last one was in place to “celebrate the life, death and reincarnation” of Jail Break as we know it now.






I had recently been to the Old City Jail for a ghost tour complete with beers during Charleston Beer Week. During that tour, our guide mentioned many times how dismal the jail was, and how primitive the building has remained through its time. He mentioned how electricity wasn’t even brought to the building until recently. Despite this, Jail Break seemed to have no problems illuminating the art cascading along the walls, or bringing sound and movement to every corner of the centuries-old haunt.





As I moved through the main opening I was instantly greeted with sights and sounds that are trademark to the festival. The bleak prison setting had been transformed into a living representation of Charleston’s art scene. Music from outdoors had no trouble reverberating through the halls that were lined with various pieces by local artists The paintings, sculptures, and installations were many and diverse, giving way to a sense of exploration in order to find relationships between them and understand their placement amongst each other.






Upon stepping into the courtyard, the striking coordination from the live dancers set a great tone for the free-spirited outdoors. I of course headed toward Hi-Wire Brewing’s tent and grabbed a beer to help, uh, loosen my senses to fully grasp everything happening around me… Afterwards I had a Palmetto Espresso Porter (or two) for quality assurance – tasting great guys! I then checked out the handmade and vintage wares being offered toward the side of the yard. At this point I noticed there was a theme in terms style. Despite being a fairly casual event, many came dressed in their best, much like the year previous; both times I left with amazing street style shots from personable, fun festivalgoers.







I moved toward the food trucks on the other side, after listening to some of the live music from Hermit’s Victory, Beach Tiger, ET Anderson and headliner Brave Baby. Despite decadent dessert being available from Kaylea’s Cupcakes, and pizza from Zombie Bob’s, I had to give Cory’s Grilled Cheese a shot. I’ve been wanting to stop in to his place on James Island but my girlfriend doesn’t like grilled cheese… let those words echo in your brain... then know that she had one of those grilled cheeses and loved it.






Between the dance breaks, and lively tunes from the music, I snuck through the jail again to see more works and poke my head into the pop-up radio station. My relationship with this festival is so young, it seems like a shame it won’t continue the way it is. But I can take solace in knowing that it’s not necessarily over per se and like some form of ephemeral art, the beauty of something sometimes lies in its fleeting nature or finality.





Writing this, I find it hard to fully capture exactly what I felt going through the event. There’s this feeling of jubilance that wraps the property no matter which section you’re in. I once had an art history teacher ask the class why people whisper in museums and galleries. It’s a good question that has allowed me to get a different perspective on how we view and appreciate art. Jail Break sets a different standard for art – it loosens the barriers for who enjoys it and how. So while I definitely have all these conflicting feelings towards the “death” of the festival as we know it, I can’t help but feel positivity and a little bit of enlightenment from it in the very end.