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 one with you today. Captain Gregory’s is located through the doors of a Sugar Shack donut shop in Old Town Alexandria, and it’s definitely worth seeking out for your next date night.

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 Sugar Shack, that's exactly what you'll find, just to the right of the donut shop's entrance.
Google Reviews
Captain Gregory's is a cozy, dimly-lit bar that is one of the most popular spots in town for a nightcap. That is, if you're in the know.
Jeff Gelber / Google Reviews
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.
douglas luccio / Google Reviews

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On the menu, you'll find a delightful array of drinks, small plates, and desserts.
Captain Gregory's / Google Reviews
Of course, the craft cocktails are what truly impress.
douglas luccio / Google Reviews
Not sure what to order? Ask the bartender for a recommendation, and prepare to be amazed as they whip up something incredible.
David Travis Freidman / Google Reviews
Whether you're a local to Alexandria or simply passing through, this may just become your new favorite neighborhood bar and speakeasy in Virginia!
Monty Patel / Google Reviews

You can make your reservation here! Have you ever been to Captain Gregory’s? What did you think of this hidden speakeasy in Virginia? Feel free to share your thoughts with us in the comments below — we’d love to hear from you! And, if you need a place to stay while exploring Old Town, check out these unique places to stay in Alexandria.

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Captain Gregory's, 804 N Henry St, Alexandria, VA 22314, USA