About Us

Gypsy Sally’s is the music venue for serious music lovers who don’t take themselves too seriously.  Our dream is to provide a comfortable, affordable and friendly space where adults of all ages may enjoy sharing great food, drink and music.

Located under the Whitehurst Freeway at 3401 K Street NW in Georgetown, Washington DC, Gypsy Sally’s second story windows look out on the Potomac River and the Key Bridge.  Featuring local, regional and national Americana acts on our stage, we hope to complement the venerable Blues Alley as well as evoke memories of Georgetown’s entertainment heyday where locals and tourists had their choice of great music clubs like the legendary Bayou, the Cellar Door, Desperado’s and Crazy Horse Saloon.

The current inspiration for Gypsy Sally’s comes from one too many nights standing on unforgiving floors, fighting for sight lines and wishing you had ear plugs (OK, so we’re obviously aging, but great sound should never require plugging your ears).  That’s why we have plenty of seats as well as a standing room area.   And you won’t need ear plugs! (Well…most nights…) We promise to try and only book bands who care about your hearing and understand that we have taken great care to design a room that eliminates the need to turn it up to “11.”

While listening to great music, there’s no reason you can’t enjoy great food as well.  Click over to our menu and you will find simple, delicious food that can be enjoyed with a satisfying selection of beer, wine and liquor.  Wherever possible, our food and drink are sourced locally to be as fresh and tasty as can be with the smallest eco-footprint.

In the end, Gypsy Sally’s greatest asset has to be its people.  It starts with the passion of the owners, David and Karen Ensor, and is carried out through its employees, all of whom share the goal of providing our customers with a great evening’s entertainment.  We’ve created the proper space, but its value can only be measured in the memories it creates.  That takes great bands, great staff and great customers.  Here’s to a memorable experience.

Staff Bios

Venue Owners Karen and David Ensor

Venue owners David and Karen Ensor, husband and wife, bring a diverse and extensive history of experience, knowledge, and passion for the live music industry to their project. David is a veteran musician, teacher and restaurant worker; Karen an attorney and business owner. Together, their backgrounds form the foundation of an ideal partnership.

Karen’s passion for music hails from her days at Vanderbilt University in Nashville, the perfect setting for developing her broad musical tastes — from The Grateful Dead to Sarah Vaughn.  Karen’s long strange trip started in Houston where she worked as a cardiac nurse, with stops on K and Wall Streets where she toiled as a transactional attorney for many years.  As a side gig, she has for decades co-owned a business with her brother.  Despite long hours in front of her monitor, Karen’s speakers are always on.   Hailing from Warrenton, VA, David Ensor, AKA Silky Dave, is a singer-songwriter whose musical roots are broad and deep.  A graduate of UVA, David has been tuned in to the thriving Charlottesville music scene for many years. While his influences may be classic — Cat Stevens, Bob Dylan and Van Morrison, to name a few — his musical evolution has been anything but. David’s dream has been to create a space where lovers of all types of music can grow and exchange, and he is excited to finally bring a mid-sized listening room to Washington DC music aficionados. Karen and David’s mutual love for music inspired the creation of Gypsy Sally’s.  They have taken great care to create the proper space — and anything they can do to spread the simple joy of listening to and talking about music, they are going to try.

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