High Times in Low Light – The Sheppard

Cloaked in darkness, the Sheppard is a low-key haunt off of Dupont with friendly service and good drinks.

Ambiance: *****

Decor: ****

Service: ****

Cocktails: ****

Overall Rating: 4.25

Having visited dozens of cocktail bars all around the US, I felt pretty confident that I’d seen it all. Yes, the dark jazz-age decor, the hidden entrances, the codes, the mood lighting – check, been there done that. So when I headed to Dupont Circle to visit the Sheppard, I wasn’t expecting to be so struck by the crimson, candlelit aesthetic. You step from the old elevator and immediately into this dark bordello with a wonderful oldies and indie-rock playlist – abruptly transitioning from worn 1970s era office building to something more luxurious and sinful. I just loved it – what can I say, I’m a sucker for candles and perfectly back-lit bars that remind me of The Shining. My light-deprived camera could not do the Sheppard justice, but you should really experience it for yourself.


Besides offering some intriguing surroundings, I thought the bar was very comfortable and the numbers of drinkers was kept manageable. Special shoutout to the superb service, with ultra-friendly bartenders making drinks and offering water at a nice clip.



With such lush surroundings one might expect an ornate and complex cocktail list. Surprisingly, the Sheppard offers fairly simple drinks done well, eschewing the more exotic ingredients and concoctions you usually find at a modern speakeasy. We sampled two of the Sheppard’s daily cocktails lists (the bar changes them every day) for a total of ten drinks, of which four were notable standouts.


I started my nocturnal journey with the “Honeysuckle,” a light mix of white rum, lime, and honey. Sure enough, that combo of honey and lime does recall that delicate flower; light, sweet, and with a sedate rum touch, this was just easy and nice drinking. Next was the “Chet Baker” with aged rum, vermouth, bitters, and honey. A bit harsh on the front end, I persevered and ending up liking Chet the more I drank – the cocktail carries some resonant honey and a powerful rum kick at the conclusion. The vermouth grants a touch of herbal on the edges, sexing up this fine drink.

Then we celebrated “Autumn in New Jersey” made of Applejack, lemon, orgeat, and bitters. I’m a sucker for both applejack and the Garden State, so it was no surprise I was a fan of this one: the standout is packed with ice and offers a powerful, orgeat-bordered herbal tinge that just slowly sinks in you sip. Nice brandy burn as you drink, this wields a sweet citrus/liquor combo so well. Drink it up. It’s that time of year with the “Income Tax Cocktail” with gin, vermouth, orange juice, and bitters. I thought this was one of the more interesting drinks at the Sheppard, with a really different orange influence that synchs well with the gin burn. A one of a kind citrus/herbal kick, nice nice.

Then the classic “Martinez” with gin, vermouth, maraschino, and bitters. This is a standout sipper, with a seemingly mismatched collection of ingredients that somehow, someway works perfectly, culminating in an exquisitly measured gin burn. Even the maraschino, which I’m not a huge fan of, plays well here, staying in the background and letting the gin and vermouth go to work. We got a bit lighter with the “Conquistador” with rum, tequila, lemon, lime, bitters, and egg white. Unlike its namesake, this wild ingredient list comes across pretty even and mild, with only a slight tequila sting. Cooled and softened by the egg, this was slightly sweet and tangy, one of the easier tequila drinks I’ve had.

The night rolled on with the “Diplomat” with vermouth, maraschino, and bitters. A very straight forward and bare bones cocktail true to its ingredients, this was smooth and heaviy influenced by the maraschino. Like, really heavily. Just ok. A standout was next with “Fairbanks” with rye, apricot, and bitters. A wild taste that pumps up the rye, I loved the peppry backbone on this one as you sip. While I wouldn’t say I loved the taste, I admired the adventure of it, a very different taste I haven’t experienced before. Worth the ride, trust me.

My favorite drink at the Sheppard came next in the “Hoffman House” with gin, lemon, orange juice, grenadine, and cream. This was just fantastic, with a milkshake-y, frothy  mouthfeel with a soft gin and citrus kiss. Easy drinking but doesn’t put you to sleep, this was a great one to sip slowly and enjoy the resonance. I finished the soiree with “Between the Sheets” with aged rum, cognac, lemon, and cointreau. This was a clean and ok drink, a little rum syrup-y taste evened with the orange liqueur taste that I liked. I didn’t quite get much from the cognac, but this was decent. What a wonderful way to end a spectral evening at the Sheppard! Get on over and drink heavily by candlelight.

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