Oh how time flies!  We can’t believe it’s already been 5 years since the opening of eclectic Washington DC music hub Gypsy Sally’s.  The venue under the bridge on K Street has been stomping grounds for us, and since its inception we’ve had so many amazing memories including People’s Blues of Richmond playing with Deaf Scene and TAUK, for their first and only DEAF PEOPLE TAUK tour, a New Year’s Eve show with The Werks, ramblin’ with the wild man and Larry Keel, funky jams with LITZ, and so many more shows and occasions.  Gypsy Sally’s does a great job with their booking, marketing to the eclectic tastes of funk, jam, and Americana music fans.

Since Karen and David Ensor opened Gypsy Sally’s with a mission to rejuvenate the live music scene, they have brought tons of nationally touring acts to DC audiences including many jam band giants such as Everyone Orchestra, The Motet, Twiddle, Pigeons Playing Ping Pong, New Riders of the Purple Sage, and most notably, John Kadlecik – who has played at the venue over 50 times. There is also the increasingly popular and always cover-free 100 capacity room, Vinyl Lounge, that hosts singer songwriters and the Tuesday night Open Mic hosted by one of the owners, who’s regularly on the sign-up sheet as Silky Dave. The venue has more recently found itself to be the epicenter of musical creativity and cultivation through hosting the Gordon Sterling Jam at Gypsy Sally’s twice a month- creating connections amongst musicians all over the DMV area. The venue also boasts a new lighting system installed this past summer which includes a ChamSys console and Rogue1 moving lights, providing an enhanced production experience for both artists and patrons.

Gordon Sterling Onstage at Gypsy Sally’s
Photo by Josh Brick

To celebrate this special 5 year anniversary, the owners have planned a special show – the music of the Grateful Dead and The Allman Brothers Band being recreated by Better Off Dead and The Allman Others Band on Saturday, September 8th.   Learn more about the show and buy your tickets here.

To mark this occasion we spoke to owner Karen Ensor about the rollercoaster of music and memories from the past five years.


Where are you originally from and what brought you to DC?

David was born in Baltimore and raised in Warrenton, VA. Karen was born and raised on the west coast of Florida. David came to DC in 1986 following his graduation from UVA and a couple of stints in Los Angeles. Karen moved here after law school to practice law downtown.

How did you find the location that was going to become Gypsy Sally’s? What was there before?

We had been seeking a DC location for over a year, when David accidentally discovered the building while riding down the Capital Crescent Trail to Georgetown in April, 2012. The structure immediately caught his interest, and sure enough there was a for lease sign on the far side of the building. It was built in 1902 and was originally an ice factory. When we visited the space, it was unoccupied and sloppily sub divided into multiple office spaces. However, we were able to look past the shabbiness and realize that after demolition we would be left with a wide open space with only one column to work around. That’s a rarity in DC where good sight lines are always a challenge because the majority of spaces are either too narrow or supported with multiple columns.

Why did you want to open a music venue, and what sort of vision did you have for your venue?

We laugh at this question – David always dreamed of opening an intimate singer-songwriter venue. Once we saw this space, Karen urged him to think bigger. We originally intended to focus on bringing Americana acts to the city. It quickly became apparent that we needed to broaden our programming and the immediate success of jam bands in the venue pointed us in a new direction. Fans will always lead the way. Insanity accounts for the rest.

John Kadlecik Onstage at Gypsy Sally’s
Photo by Josh Brick

What did you learn and how did you grow over this past 5 years?

We have found that if you do your best to remain true to your authentic selves and create a family environment, then you will be rewarded with loyal employees, patrons and musicians. We are a mom and pop business, relying on faithful bands and patrons, not the deep pockets of other business ventures. Gypsy Sally’s now has a life of its own. We are the caretakers, but it’s the patrons and bands who are forging the path. If we need to correct course, they will let us know.

What are one or two highlights and amazing moments from the past 5 years?

We would be remiss in not mentioning our anti-inaugural fundraiser for Planned Parenthood and Electronic Frontier Foundation in January 2016 – featuring the  Bureau of Sabotage ft. John Kadlecik, Oteil Burbridge, Aron Magner and Jeff Franca. Our friendship with John Kadlecik has been one of the most rewarding facets of this business – and John has made this venue his home base playing over 50 times here. And lastly, nothing is more rewarding then having a major national touring bands play in your venue, and we’re lucky to say that we’ve hosted some of our favorite bands, notably Leftover Salmon, Steve Kimock, The Motet, Turkuaz, and so many more.

What are some difficulties that you’ve learned to overcome?

Learning to be patient when the competition gets tough and realizing that if we remain true to our vision, employees, customers, and bands alike, then business will flourish.

What are you looking forward to in the near future?  

It’s always exciting each September as we look forward to the fall shows culminating in a NYE celebration. This fall kicks off with great shows like Larry Campbell and Teresa Williams, ALO, and Particle. Just before that we will finally make it to the beach to relax for a moment and to recharge for the busy season.

What are you looking forward to in the distant future?

Getting back to the beach.