Gypsy Sally’s was one of the first venues where I began photographing live music in Washington, DC. As my “career” in concert photography was just getting started, in January 2014 (and again a few months later), I took my camera to photograph River Whyless, a new band from Asheville, North Carolina. A local duo, Pretty Gritty, was opening.
Little did I know that over the next few years Gypsy Sally’s would give me the opportunity to see and photograph an incredible variety of local and national touring musicians.
Having opened in 2013, Gypsy Sally’s was still making a name for itself in those days. Between the main stage and the Vinyl Lounge hidden around the back of the building, both established artists and newcomers played GS, and over the next six years, the venue would become one of DC’s most cherished. And for a neophyte live music photographer, it afforded me a wonderful learning ground and the opportunity to see, up close, some of the world’s finest musicians.
David and Karen Ensor opened Gypsy Sally’s, located in Georgetown underneath the Whitehurst Freeway at a time when the live music scene was concentrated in the U Street Corridor with venues like 9:30 Club and Black Cat. “When we got this place, the nostalgia certainly kicked in,” David, a musician himself, told DCist in a 2017 interview, “Georgetown used to be cool with great live music venues like The Bayou and The Cellar Door.”
Gypsy Sally’s had its final loadout on Jan. 5, 2020, after local guitarist, Dark Star Orchestra founder, and GS regular John Kadlecik performed at a series of final shows at the venue mere weeks before the Covid-19 pandemic shut down music venues across the country. And although we’ll never know if GS would have survived the pandemic, I’ll always be grateful for its sublime acoustics, terrific sightlines, superb lighting, and ownership and staff that provided the DC area with six years of the best music anywhere.
All photographs courtesy and copyright Mark Caicedo/PuraVida Photography
