drink local

Look for the Green Light: Zelda's Speakeasy

By / Photography By | October 20, 2022
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Owner Jeff Maguire behind the bar at Zelda's

On a Thursday or Friday night in Chestertown, Maryland, when all of the businesses along the intersecting High and Cross Streets turn off their lights and lock up their doors for the evening, thirsty patrons have few options if they are looking to burn the midnight oil. But not all those who wander the downtown streets are lost, for there is a knowledgeable crowd who know where fresh beer flows from the tap and where cocktails are expertly shaken. They know to look for the elusive green light shining just below a second story window, calling all ships to shore, offering safe haven from the storm.

The green light belongs to Zelda’s Speakeasy. When the light is illuminated, that signals to locals that Zelda’s is open. It is a recognizable sight. In his classic novel, The Great Gatsby, F. Scott Fitzgerald wrote of the green light: “Gatsby believed in the green light, the orgastic future that year by year recedes before us. It eluded us then, but that’s no matter—tomorrow we will run faster, stretch out our arms farther…” For Fitzgerald and his characters, the green light was a symbol of a better future.

Zelda’s shares its namesake with Fitzgerald’s wife, the well-known socialite often considered to be America’s first flapper. It was during their time that prohibition shut down legal drinking venues, prompting creative entrepreneurs and shady underworld figures to set up operations in shadowy, hidden locations. Speakeasies offered a place of refuge, an underground facility for parties, and a venue for the Lost Generation - the writers and creatives of the post-World War 1920s. The group of writers, including Fitzgerald, who wrote about the promise of the American Dream and the shattered reality of those who were never able to attain it.

It is these timeless portrayals of the American experience that Zelda’s owner and sole bartender, Jeff Maguire, feels a strong connection with, and the reason why Fitzgerald’s muse was his choice for the bar’s name.

Jeff does not do any marketing for Zelda’s. There are no social media posts, no advertising in local papers, and there is a minimal digital footprint at best. That may sound counterintuitive for a business, but Jeff has created an experience that he wants you to arrive at naturally. Zelda’s is a location that you hear of through a soft whisper at a party, or that you happen upon when you glance up at the dreamy green light cutting through the mist and fog. In a world where clicks and likes are a main motivating factor in many of our lives, it’s refreshing to find a place that sets the current playbook ablaze.

Inside, Zelda’s is eclectic. The speakeasy is an original that stands apart from the carbon copy sports bars and mass market franchises. And, let’s be frank, where you drink matters. The ambiance, the crowd, and the four walls surrounding a bar can color the experience.

At Zelda’s the walls, floor, and ceiling are lined with mementos, tokens, and memorabilia from Jeff’s well-lived past. These totems all tell a story, and they provide a backdrop of Easter eggs that lead visitors down the different paths of Jeff’s experiences. Dozens of photographs from his life adorn the free spaces on the walls. The animal print wallpaper that lines the bar wall with zebras is a relic from his childhood. Guitars, travel souvenirs, sports memorabilia, artwork, empty bottles, and countless trinkets all tell a tale. Perhaps most special, is a Moet bottle that was a gift to Jeff from the general manager of the first bar he worked at during his college days. He received the gift on New Year's Eve in 1987. Spending a night at Zelda’s is like falling into a child’s toy box, if that child was an ageless proprietor, equal parts whimsy and hard work.

You won’t find a staff at Zelda’s. There is no host to greet you, no bar backs, no one washing glasses and running them to the bartop. Jeff is a team of one. He glides from drinker to drinker, often remembering their favorite drink before they get a chance to order. On a recent visit, Mary Cassidy of Galena explained to me that Jeff never forgets his customer’s go-to drink, always remembering from visit to visit. Most nights patrons tally their own drink totals in their head and pay before leaving at the end of the night. It’s a mutual acknowledgement of trust, which adds to list of attributes that make Jeff many people’s favorite local bartender.

When Zelda’s light is turned off, it means that the door isn’t open to the public, but it doesn’t mean that the party has died down. Jeff rents his services and the space for private parties and events. I was fortunate to attend one, albeit as an interloper, when a wild and rowdy crew of Marylanders celebrated a friend’s birthday. Jeff kept every glass full as music kept the partygoers moving, and a disco ball spun the minutes away. I took notice of the many trinkets and idols of Jeff’s past, trying to find the meaning in them all. A quick glance out the window showed the street outside had gone completely dark, making Zelda’s the lone bright spot on the strip. It truly felt like a hidden, secret club, a trip back to the days when such places were outlawed.

Generally speaking, this is the part of where you would read about the hours and location of the place that is being written about. But Zelda’s is a speakeasy, and I will treat it as such. Instead, I’ll leave you with just one sentence, one that stays in line with the spirit of Zelda’s, that will set you down the path of your own adventure: Look for the green light.

Zelda’s Speakeasy
South Cross Street, Chestertown, Maryland
(It’s as much as we’ll say…)

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