It was sometime back when I mentioned Captain Gregory’s and my intension to visit this sweet hole in the wall speakeasy sometime soon. Well, we finally had the chance over July 4th weekend. We decided to drop by the Saturday the week before but it was booked and we got on the waiting list. After an hour @ 10pm and rain pending, we cancelled when they texted us. Instead, we made reservations for the following Saturday.
There is a $25 / person minimum on Friday and Saturday nights. We had no problem meeting this and then some, with just 2 drinks, it’s easy to do.
Front room seating
We went early for the first seating at 6 pm, when our cocktail hour usually starts. This was a good idea, as we could also get some appetizers and start the evening early. We had a chance to view the Sugar Shack — the doughnut shop — where Captain Gregory’s exists, located behind a secret wall.
Love these doughnuts and crafty decor. One is even a disco doughnut.
It’s a hole in the wall entrance. The flag is the “doorbell”
We sat right at the bar, far left side, as seen in their website homepage photo. This was the perfect placement to watch the bartenders command their craft. This is about as big as the place is. Seats 24 with two rooms and around the bar. The ambience is just right with low lighting and the great range of music sets the vibe. Thursdays happens to be bring your own vinyl night, which we’ll have to try.
Sam Brooks was our bartender extraordinaire. However, if you forget anyone’s name their chalkboard sign says just call them “Captain.” Sam, our cocktail captain, really knows what he’s doing. I started with his Sudden Downpour in Manila an unusual pairing with Banana and red miso infused bourbon and burnt sugar with Angostura bitters. Peter started with (13th Street Cocktail) with Rittenhouse Rye, homemade sweet vermouth, Yellow Chartreuse, Frenet Branca, Angostura, and Applewood Smoked — served room temperature. This takes a special palette to enjoy but reminds me somewhat of a Last Word. Both were wonderful with flavors that I would have never thought to use together.
Sudden Downpour in Manila cocktail
Unfortunately, the menu on their website is not current, and after another 3 drinks, I don’t remember all the details for the remaining ones.
There were too many tempting cocktails to try but I decided to put Sam to the test with a custom Vieux Carré and a Cardamaro Sour, because afterall, we were there because of Tyler’s suggestion from when we experienced Magnolia’s, with his same custom cocktail creation. Sam’s was good but Tyler’s seemed better, however the Captain’s had more, so toss up…
Specially concocted Cardamaro Sour at Magnolia’s
Peter like his 13th Street Cocktail so much that he had another; whereas, I wanted to try different drinks. My final concoction was the homemade daiquiri with singed anise. This important detail added taste through smell every time you took a sip and exemplified the true art to making a cocktail terrific.
We enjoyed a wonderful cheese board and because there is a 2 hour limit, which is a good cutoff time, we had a couple of doughnuts to enjoy on our walk home, which fortunately, is nearby. Luckily for us.
Homemade Daiquiri with singed anise
We’ll be back of course but may have to make reservations way in advance as the place may have lost its secret status with this recent bit of great press they’ve experienced. Otherwise, you’d never guess such a sweet spot exits in this unassuming doughnut shop.
Unassuming Sugar Shack entrance right on Route 1 highway in Old Town Alexandria, VA
Dallas Daily News – Seven Places to Toast the Art of Drinking in Alexandria, VA
Southern Living – The Sweet Life of Alexandria, VA
In A DC Minute – 5 Places to Get Cocktails in Alexandria
DC Refined – 8 Cocktail Bars that Command More Attention
Washingtonian – Captain Gregory’s Speakeasy is Serving Doughnut Sliders and Sundaes