Tucked in hidden alleyways and behind disguised doors lie some of the state’s best-kept secrets … and cocktails. Speakeasies promising vintage vibes and low-light charm dot the map far and wide, but where to find them? Here are 10 to get you started on a journey to delicious drinks and illicit adventures of 1920s allure.
The Alley Light
108 2nd St. S.W., Charlottesville
Reveal Hidden Entrance
You’ll find this secret spot down an inconspicuous little alleyway off of 2nd Street Southwest, through a door underneath—you guessed it—an alley light.


Anastasia’s Speakeasy
390 Franklin St., Rocky Mount
Reveal Hidden Entrance
Upon entering the building at 390 Franklin Street, you may be confused—expecting a luxe restaurant and bar with vintage trappings and instead stumbling into what seems to be an old-timey barber shop. Fear not; the entrance you seek is through a hidden door behind the green vintage candy machine.
Facebook.com/AnastasiasSpeakeasy
Captain Gregory’s
804 N. Henry St., Alexandria
Reveal Hidden Entrance
The term “hole-in-the-wall” rings true here, where the entrance to the intimate, cozy cocktail space is through a trick wall in Railbird Kitchen, the front-facing restaurant. Ring the doorbell (an innocent-looking flag hanging on the wall) and a doorman will fetch you to come inside.



Fin & Tonic
1301 Bridgeport Way, Suffolk
Reveal Hidden Entrance
A hidden door panel adjacent to the bar at this seafood restaurant leads to a smaller exclusive speakeasy room, where reservations are recommended.
Grandstaff & Stein
2113 E. Main St., Richmond
Reveal Hidden Entrance
Behind a false bookcase and a password, which you’ll have to check their social media for, as it changes weekly.
Heirloom
1871 Fountain Dr., Suite 300, Reston
Reveal Hidden Entrance
This jazzy food and drink escape is tucked inside Open Road Distillery in Reston Town Center. The entrance is an unmarked, ornate door subtly placed near the restrooms.
Jack’s Hideaway
92 S. Main St., Harrisonburg
Reveal Hidden Entrance
Their website instructs visitors to knock on the gray door behind 92 South Main Street to enter their realm of clandestine atmosphere and creative, 1920s-esque cocktails.
Lost Saint
333 W. Main St., Charlottesville
Reveal Hidden Entrance
Charlottesville’s Tavern & Grocery has a magical secret lurking below: a speakeasy that seems to transport one back in time. The basement bar is accessed through an entrance marked “LS,” and staff can help point the way.
Steak & Tonic
11810 Fountain Way, Suite A, Newport News
Reveal Hidden Entrance
This sister restaurant to Fin & Tonic doesn’t disappoint with a surreptitious speakeasy of its own, this one found behind a door masquerading as a wine storage wall.
Trading Post Speakeasy
113 13th St., Lynchburg
Reveal Hidden Entrance
A little easier to find than others, this speakeasy entrance is marked but still lodged in a little alleyway. Plus, its old barrel tables and classic billiards add that touch of back-in-time atmosphere.