A new speakeasy-style bar is coming to Old Town Winchester. 18th Rebellion, a 1920s-themed bar named after the constitutional amendment that started the Prohibition era, will open its doors on September 16.
This venue is the newest venture from Monument Entertainment, which operates The Monument entertainment venue and its concessions concept Know Concessions, and Ellie’s Pub, all in Old Town Winchester.
18th Rebellion will be a separate bar concept on the basement level of The Monument. The building was built in 1922 as a bank, and the owners converted the lower-level spaces that were originally used as vaults into a bar and lounge, according to director of operations Justin Tenpenny.
The aesthetics of the bar will play off of both the history of the building and the 1920s, with details in the furniture and on the walls. The leather tables with steel bases, hand-tucked upholstery, and wood-textured concrete walls all give nod to the era that inspired the space.

“There’s like these little, tiny pieces of history that are almost fossil-like, in the way that things were done at that time,” says Tenpenny.
And it’s not just the ambiance that will make visitors feel as though they’re traveling back in time. The menu was curated to pay homage to the customs of the period. That means an emphasis on bourbon and whiskey, mescal, and moonshine. The restaurant even took advantage of Virginia ABC’s lottery system to help get its hands on some rarer whiskeys.
For beer-drinkers, there will be a “pre-Prohibition lager,” made in collaboration with Brothers Brewing Company, that mimics the brewing style that brewers used in the 1920s. This is a less hop-forward beer that uses yarrow to bitter the beer.
“The staff is going to be storytellers, so they’ll be able to tell you the nuanced history of a particular bourbon and why menu items named what is named,” Tenpenny says. “[They’ll] tell stories. Because anybody can just make a cocktail, but not anybody has nuanced stories, too.”
As for food, there will be a seafood-forward menu of tapas-style offerings, which will draw culinary inspiration from Southern French and Mediterranean cuisines.

And though 18th Rebellion and The Monument are separate operations, there is a sense of connectivity between the two. TVs throughout 18th Rebellion will livestream concerts from The Monument so that concertgoers won’t miss anything if they go downstairs for a drink. Plus, some customers who dine at 18th Rebellion before attending a concert can gain early entry to the event.
The venue management hopes that this new concept will help contribute to the economic vitality of Old Town Winchester by creating an interesting destination that will draw visitors to the area.
“Being in a bank and being in this historic building, being in a historic marketplace, we wanted to create a concept in the Old Town Winchester area that would require it to be a destination,” Tenpenny says.
The venue will first open its doors during Fiddles & Fifths, a music festival in Old Town Winchester that will feature bluegrass music and Virginia bourbon. The festival begins at 4 p.m. on September 16 and will include a performance by The SteelDrivers.
Festivalgoers can head down to 18th Rebellion during the event. Reservations will be required and can be made online beginning about a week before the event.
186 N. Loudoun St., Winchester
Feature image by Capture PH
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