This Speakeasy Hidden in Old Town Alexandria, Virginia Is Perfect for a Date Night

There's something so alluring about speakeasies, isn't there? Off-the-beaten path and shrouded in mystery, these places make us feel as though we've traveled back in time. Finding them can be somewhat difficult, as they are by nature kept a secret, but we'd like to share a special one with you today. Captain Gregory's is located through unsuspecting doors in Old Town Alexandria, and it's definitely worth seeking out for your next date night.

How To Find Captain Gregory's

Walking along Henry Street in Old Town Alexandria, you'd hardly expect to stumble upon a speakeasy. Yet if you walk through the front doors of 804 N Henry Street, that's exactly what you'll find, just through the doors and to your right. This building used to be a Sugar Shack before it was replaced by a few other local businesses, but Captain Gregory's has remained a constant.

On the Menu: Light Bites and Delicious Drinks

Step through the wood-paneled doors into Captain Gregory's and you'll discover a cozy, dimly-lit bar that is one of the most popular spots in town for a nightcap. That is, of course, if you're in the know. Reservations are highly recommended for this spot, so be sure to plan ahead. Step inside, and you'll feel like you've traveled to somewhere truly magical—and very secretive. On the menu, you'll find a delightful array of drinks, small plates, and desserts.

Of course, the craft cocktails are what truly impress. Some favorites include the High Seas Diplomacy, made with American rye, overproof rum, passion fruit, coconut, and demerara sugar. For something wonderfully unexpected, order the Royal Banana Syndicate, complete with aged Caribbean rum, bourbon, sweet vermouth, banana peels, and pecan praline.

Don't skip the food, though, which is equally as creative and inventive as the drink menu. Think: lobster salad, ahi tuna, pork belly, and more, all crafted with care.

Not sure what to order? Ask the bartender for a recommendation, and prepare to be enchanted as they whip up something incredible. Whether you're a local to Alexandria or simply passing through, this may just become your new favorite neighborhood bar and speakeasy in Virginia!

You can make your reservation here! Have you ever been to Captain Gregory's? What did you think of this hidden speakeasy in Virginia? If not, be sure to share this article with a friend or date and begin planning your speakeasy adventure! Feeling inspired? Try planning your own trip using Only In Your State’s itinerary planner.

Looking for related content, take a look at this list of our 12 favorite restaurants in Virginia to try this year.