Our Vision
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 enjoy sharing great food, drink and music.  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.

Our Specs
Gypsy Sally’s is comprised of three separate spaces, the largest space devoted to the Music Room. Gypsy Sally’s also offers the Vinyl Lounge where patrons can enjoy music from classic vinyl records, and the Microbus Gallery, both of which are perfect for private events. Located under the Whitehurst Freeway in Georgetown, the 1902 building was formerly an ice factory and is generously proportioned with tall ceilings perfect for live music.  An Americana theme pervades the place, with authentic barn wood, American flag murals and even an antique VW bus.

The Music Room is a 4000 square foot listening room with a state of the art sound system.  Its inspiration comes from one too many nights standing on unforgiving floors, fighting for sight lines and wishing you had ear plugs.

That is why most shows will offer a mix of Reserved Seating and General Admission — with plenty of room to stand (and dance, dance dance!) for those that prefer it.  And on-line ticket buyers will be able to choose an exact seat (or barstool) at the time of purchase.

The room is designed with tiered seating platforms to improve sight lines and has had acoustic treatments to ensure great sound.  Consulting on the audio equipment are two of the area’s best: Greg Lukens of Washington Pro Sound and Tim Kidwell of The Birchmere.  The music room boasts a 300 square foot stage, and has a capacity of approximately 300, depending on the evening’s entertainment.

If Gypsy Sally’s music room is focused on the present (with occasional glimpses   into the future), then the Vinyl Lounge is a fond nod to the past.  With its warm red tones, comfy stools, and inspired repurposing of records, the lounge is the perfect spot to wax about the good ol’ days of vinyl. The Vinyl Lounge, open daily, is a separate “no cover” eating and drinking lounge which has its own entrance behind the building on 34th St.

Gypsy Sally’s is a special space that brings a new sensibility to DC music lovers. Karen and David Ensor have taken a thoughtful approach to every aspect of the Club — from the sound (musicians are already touting Gypsy Sally’s as the best sounding room they have ever played!), to the sightlines (“not a bad seat in the joint!”), to the food and drink offerings.

After profiling venues from Florida to Maine (well OK, maybe there also were a few road trips to points West as well), Karen and David believe they have configured  the ideal personality for Gypsy Sally’s — a room that above all sounds and feels great, but one that also is flexible enough to welcome acts that appeal to a wide variety of ages and musical tastes.

Headliners typically will take the stage on the early side, offering an option for city workers who want to stay downtown and catch dinner before the show.  And rather than closing up after the main show, Gypsy Sally’s will offer its later stage to different local or regional artists.

Gypsy Sally’s is first and foremost a listening room, so patrons at most shows will be asked to silence their devices and refrain from chattering, but the Vinyl Lounge is just steps away for the friends who just have to yak and catch up before settling in to enjoy the live act.

Gypsy Sally’s also wants to dispel the notion that you can’t enjoy great food and drink while listening to great music.  Our menu, another riff on the Americana theme, boasts wide regional flavors drawn from many different ethnicities. Expect simple, delicious fare that emphasizes every aspect of the F.L.O.S.S. philosophy: Fresh, Local, Organic, Seasonal and Sustainable.  Acronyms aside, the Ensors are committed to joining a movement that is not only good for their business but good for the environment as well.  Libations have not been overlooked — in addition to premium spirits and craft beers, DC music lovers can enjoy Gypsy Sally’s reasonably-priced selection of respectable wines.


Our Team

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 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.

Directing Gypsy Sally’s kitchen is Donald Spencer, an experienced chef coming from Range, Bryan Voltaggio’s Friendship Heights eatery, and before that, 2941.   “Chef” has a simple philosophy for his food: “it has to be fresh and it has to be interesting.”

Booking Gypsy Sally’s Main Room is Wil Gravatt of Gravatt Entertainment.  A veteran of the DC-MD-VA music scene, Wil is stoked to apply his experience to DC’s newest mid-sized listening room.

To download high-definition archival photos, please refer to the GALLERY at

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