I don’t own a boat, so the only way I know to get to Chestertown, MD is by crossing the Chester River Bridge. It’s a low-slung, drawbridge type, built in the 1930s back when they really knew how to build stuff like that. I’ve been looking forward to this for weeks, finally getting a chance to stay in Chestertown – I’ve passed through a couple times, eaten dinner, maybe had a drink, but nothing of substance. I turn onto High Street, and I can see my home for the next few days, a bed and breakfast, The White Swan Tavern. There’s an empty parking space right out front. Man, I love small towns.

Sarah Crump manages the historic White Swan Tavern. Photo by Jim Burger for Main Street Chestertown

Sarah Crump, the effervescent day innkeeper, greets me at the door. In a town with lots of old stuff, the White Swan is still considered old. A restored eighteenth century public house with creaky floors, everywhere you turn is dripping with history. There’s even a museum quality display of artifacts from an archeological dig conducted in the 1970’s. I dutifully examine it while Sarah retrieves my room keys. She leads me up a winding staircase to an imposing wood door. I read the brass plate, “1854 – 1977 T.W. Eliason Suite.”

Me: “T.W. Eliason lived to be 123 years old?”

Sarah: No, T. W. Eliason’s family owned the building that long.”

Me: “My story is funnier.”

She unlocks the door and hands me an eight-page booklet on the restoration of the tavern. I read a little of it every night, and by the time I checkout a couple days later, I’m ready to write my dissertation. Before she leaves, Sarah, in a hushed and very serious tone, tells me that I’ll be needing a drink tonight. I nod my head in agreement. “Go to Zelda’s Speakeasy on Cross Street. If the green light is on, it’s open. Just don’t tell too many people about it, that’s my hangout.” Considering we only met five minutes ago; Sarah seems to know me very well.

I walk out of the inn and wander down the street, passing the newspaper office. The hand-painted sign above proudly proclaims, “Kent County News. A Direct Descendant Of The Chestertown Spy, Established 1793.” I keep walking, and I can’t put my finger on it at first, but then it finally hits me…The Chestertown Spy is a much cooler name. I would have stuck with that. I can smell the Evergrain Bread Company before I can see it, and when I get to the corner of High and Queen Streets, I can’t help but go in. I get a black coffee, and something called a “Sun Bun.” I don’t know what it is, but I want it. Sitting at a table out front I drink my coffee and eat my Sun Bun. My phone rings. The name that comes up is “Ellen Uzelac,” an old friend and writer from my Baltimore Sun days, now living in Chestertown.

Evergreen Bakery's miraculous Sun Bun
In Chestertown, Evergrain Bakery’s Sun Bun is a revelation. Photo by Jim Burger for Main Street Chestertown


“Are you in town?”

“Yes, I’m in front of the Evergrain Bread Company eating a Sun Bun, it’s amazing.”

“I’m half a block from where you’re sitting.”

I look around. “Honey, everything in Chestertown is half a block from where I’m sitting.”

Ellen’s gingerbread house is further down High Street. We sit in wicker chairs on her front porch with our feet propped up on the railings. An American flag glows in the sunlight, and catches a cool breeze. Back when I met her, she described herself as having “itchy feet,” an aversion to staying in one place for too long and yearning to travel. That was true. She had lived all over the country, as well as abroad. And yet Chestertown was the place to rein her in – she’s been a permanent resident since 2001. It’s easy to see the appeal. From our perch we watch the citizenry come and go, ambling along the irregular, hand-laid, brick sidewalks (a cement contractor would probably starve to death here). It’s this place that energizes her writing, but not be overlooked are the more tangible attractions. She points to Stam’s Luncheonette, an ice cream parlor up the street. “Stam’s changed the dynamic. It’s a joyful destination, and now there’s an energy downtown.” I ask her favorite flavor. “Mint Chips.” Knowing Ellen as I do, I know it’s impossible for her to have just one favorite anything, so I wait. “And Cookies and Cream.”

Keke, Chestertown’s bookstore cat, snoozes, when not guiding customers, at The Bookplate. Photo by Jim Burger for Main Street Chestertown

I don’t have to ask anybody if there’s a good bookstore in town, places like Chestertown always have a good bookstore. I find The Bookplate on Cross Street, and its affable owner, Tom Martin, just where I’d expect him, behind a stack of books. His shop is exactly what you want in a bookstore, cluttered, but organized, and a cat curled up on one of the comfy reading chairs. And the best part, the place smells like books. To a book lover, nothing smells better. Martin has that erudite swagger of someone who got to Chestertown via Detroit and Washington, DC, and boasts of his shop needing more shelf space to hold its 50,000 books. It looks like 49,000 to me, but I learned long ago not to mess with anyone from Detroit. Just then Jon Hanley clomps through the front door wearing heavy rubber boots. He’s Chestertown’s handyman and works for Martin, building the aforementioned shelves. But today he tells me he was on something called, “Fountain Duty,” the maintenance of the town’s decorative water fountain in the park, and encourages me to check it out. I walk down Cross Street and find the fountain – it’s hard to miss – a cast iron, Victorian era pile, painted aqua. Water splashes from everywhere – the urn and goblet held by a bare-chested muse, the upraised beaks of swans, and out the mouths of pink-tongued lions. When people picture a fountain on a village green on pleasant afternoon, it’s this fountain they’re imagining.

At 4 p.m. I meet up with Baltimore expatriates Kay MacIntosh and Carolyn Spencer Brown. They too relocated to Chestertown years ago, and show no signs of ever leaving. We sit outside at Casa Carmen Wine House, a bodega on Cannon Street, opened by vintner brothers Enrique and Felipe Pallares as a vehicle to sell their signature wines. Plates of bread and cheese appear, and a bottle of Viognier, followed by more of everything. At the next table Eric Graupensperger enjoys the late afternoon light with Laura Peppler and her mother Sandra. Their conversation becomes our conversation, and soon we’re one big happy family. A couple walks by carrying what’s left of their bottle of Grüner Veltliner, and offers to refill my glass. At Casa Carmen, mi casa really is su casa. No, seriously.

Sarah wasn’t kidding about the green light at Zelda’s Speakeasy. I find it on later that night, and climb the stairs to the taproom above Play it Again Sam, the coffee shop on Cross Street. There’s something about walking up a set of steps, or down a set of steps, to get to a bar that makes it seem like you’re getting away with something. Behind the bar, owner/bartender/master of ceremonies Jeff Maguire swiftly moves from customer to customer, drink to drink, pulling drafts and mixing cocktails.

Zelda’s Speakeasy is a recent addition to Chestertown’s cocktail scene, and is owned and created by longtime bartender Jeff Maguire. Photo by Jim Burger for Main Street Chestertown.

He has achieved something rare in a barroom, repurposing bad office space and striking that delicate balance of proper light and noise level, appropriate music and volume, no television blaring, sufficient seating clusters, and even the right number of pianos (one). If you want to avoid people there’s an outside deck, and if you want to avoid the people avoiding people there’s a secret courtyard. I sip my Martini and compliment Maguire on his creation made to my demanding specifications. It’s second nature to him, he’s been doing this for 34 years. He even remembers his first-time tending bar and the name of the barman who didn’t show up. Maguire was pressed into service and has been tending bar ever since. I suggest we all raise a glass and thank a man named Mark MacNamara, wherever he is, who didn’t come to work one day in 1986.

Sleep comes easily after a day like that, and the White Swan is very quiet. But even being awake in the middle of the night brings its pleasures – listening to the mournful bell in the Stam’s Hall clock tower chime out the hour every hour as it has done since 1886. Every day I take breakfast in my room, never the same, always delicious. Town and country meet on Saturdays in Chestertown, and according to the canvas bags placed over the parking meters, that means the weekly “Award Winning Farmers Market.” Throughout the morning I ask vendors and customers alike, but no one seems to know where this award is kept.

Chestertown’s Farmers’ Market, held Saturdays from 8 a.m. – noon, attracts a huge variety of vendors, from locally produced farm-stuffs to crafts. Photo by Jim Burger for Main Street Chestertown

Two blocks of High Street are blocked off with barricades, and in between all manner of supplies for fine living are within reach. Lockbriar Farms sell fresh fruit and vegetables. Cheerful Echoes Farms has fresh eggs, cakes, pies and bread. The word “Fresh” really gets a workout today. There are also fresh flowers, fresh cut soap, fresh seafood, and fresh roast coffee.

Jim and Bert Lindauer of the Flying W Farm are selling their old-fashioned smoked meats, as they have been for 13 years. Bert tells me at any given time they have between 60 – 65 head of Highland Cattle on the farm. In the possible, but highly unlikely event that one of those cattle should escape, the Chestertown Lions Club is across from their booth, raffling off a shot gun.

At the Chestertown Farmer’s Market every Saturday morning, Julie King’s mushroom stand, with 8 local varieties, there’s almost always a line. Photo by Jim Burger for Main Street Chestertown.

A line forms to purchase mushrooms from Julie King. She sells seven or eight kinds, as well as marinated mushrooms, Hungarian Mushroom Soup, and, wait for it…wait for it…tincture of mushroom. That’s liquid mushroom in little eyedropper bottles. Yes, tincture of mushroom is actually a thing. She asks me what my favorite mushroom is. Ugh. I hate questions like that. I completely panic, and point to the mushroom that looks like a mushroom, the mushroom a little kid would draw if told to draw a mushroom, the mushroom that gets cut up and put on a pizza if you order a pizza with mushrooms at a bowling alley. Julie says, “Those are Cremini. They’re boring.” See what I mean? I knew that would happen! But if I would have said Shitake or Portabella, she would have known I was lying.

Right next-door Bob Walton is selling the wares of the Happy Chicken Bakery for Chef Zach Ledoux and his wife Martha. He has sandwiches, baked goods, and even gigantic Rice Krispies Treats. I can’t resist, and ask about the name, Happy Chicken. He replies, “Because they’re happy. We’re using their eggs, and not them, for food.” He actually had an answer to that question. I didn’t see that one coming.

After a busy and successful morning selling seafood at Chestertown’s Saturday farmers’ market, Josh Gannon and his assistant, Nick Bednarek are ready to head to Zelda’s for a post-market beer.

Near the end of the morning, Josh Gannon of the Waterman’s Wife Seafood Stand, and his assistant, Nick Bednarek, are packing up. They’ve sold out of just about everything. The prepared seafood completely sold out. Just a few items on the fresh seafood board remain. It’s been a good day, and they’re going out for a beer. I ask where, and Nick says Zelda’s. That’s great. That’s just great. Sarah’s going to think I told them. A little after noon, the police remove the barricades, the five miles per hour traffic returns to High Street, and Chestertown resumes its frenetic pace.

Fueling my daily Sun Bun fix I stop back in at the Evergrain Bread Company. Behind the counter Lindsey Strauss and Sydney Christian are busy restocking the display case after the morning rush. I happen to meet its founder, Doug Rae. He started baking in his stepfather’s garage 15 years ago, baking bread for his college friends, and later selling bread at markets. The bakery celebrates its 10-year anniversary in November. Rae heaps praise on his employees, including his front of the house manager, Maddy Bilinski, and allows me to pay my compliments to his pastry chef Abby Robson. As I leave, I find Fred Keer, Rae’s stepfather sitting at a table in front of the bakery.

Me: “I just met your stepson.”

Fred: “Did he tell you he started baking in my garage?”

At Bad Alfred’s, a brewpub and distillery, the locally-named pizzas reign supreme as well. Photo by Jim Burger for Main Street Chestertown

I enter Bad Alfred’s Brewpub, chasing rumors of good pizza, and grab an open seat at the bar. Too early for me to drink, so I’ll live vicariously through the two sisters sitting next to me, Darlene Dillard and Nickie Phillips. They’re from Delaware and discovered the place last year during a daytrip. “We wanted Stubborn Mules,” says Darlene. A Stubborn Mule is one of the pub’s three versions of the Moscow Mule. This one is made with “Girl Shine,” Bad Alfred’s own apple flavored brandy, distilled onsite. The good pizza rumor was true, it was terrific, and I got to have several short conversations with the owners, Al and Jennifer Cassinelli, as they mixed drinks in front of me. They do everything there, and even as I shoot a photo of Darlene and Nickie, Al appears in the background cleaning up a spill in the dining room. Just as the sisters’ second round of Stubborn Mules appears, so too does Nicki’s husband, Dale. He’s their designated driver. I didn’t get to say goodbye to Al before I left. Jennifer told me he was back in the kitchen doing dishes.

To prove the old adage “The apple doesn’t fall far from the tree,” look no further than the side by side shops on Cannon Street of Chestertown Electric, and The Listening Room. They’re owned by the father and son team of David and Michael Hoatson. The elder Hoatson is one of those friendly guys who can fix anything, and has fashioned his shop crammed with antique fans, telephones, lamps and heaters into something looking more like a museum. Hoatson the younger carries on the traditions started by his grandfather, repairing what he calls, “Classic vacuum tube stuff.” During my visit he showed me a CD player for $18,000 and a turntable for $28,000. And yet, the rooms packed with classic vinyl are the real draw. “It’s a college town. You have to have records.”

Crowds form and disperse all day in front of Stam’s Luncheonette, Chestertown’s premier ice cream parlor. People stroll in every direction with cones, sundaes, and milkshakes. Laura Martin stands in line with her sister Mallory Zupancic, and her young son, Beau. Before they order, Beau asks the question on everyone’s mind these days, “How are we going to eat ice cream with our masks on?”

Stam’s Luncheonette, opened after a major refurbishment of an beloved pharmacy/ice cream parlor, “adds new energy to Chestertown,” says local Ellen Uzelac. Photo by Jim Burger for Main Street Chestertown

The block in front of The Kitchen is once again closed for the evening, the occasion being the open-air dining experience, “Chestertown Al Fresco.” A farm wagon and planters serve as traffic barriers. Under strings of bare electric lightbulbs, tables are laid out with white linen, china, and silverware. I’m eating during the second seating, so I have my happy hour cocktail at The Pub at The Kitchen at The Imperial. Excessive use of articles notwithstanding, it’s a sweet little bar. Joseph Schultheis mixes my Martini and looks at it with a kind of detached curiosity. “I’ve been a bartender for 30 years, and I’ve never had one of those. Me and gin don’t get along.” He doesn’t have to get along, it’s perfect. Experience pays off.

I sneaked a look at the menu earlier, so I knew I was ordering the Steak Frites, but among the other selections was Crab Cakes, Rockfish, Beef Tenderloin, and Stuffed Brook Trout. Dining manager Sheri Troup reported 130-140 dinners served, flipping all the tables, and even taking a couple walk-ins.

I, along with a few other diners, walked to the waterfront before turning in for the night. Out in the channel, the yacht Calypso was anchored, gently rocking. In the morning it motored off to parts unknown.

A tree grows on the second floor of the building at 215 High Street. It’s not a real tree obviously, but one created from wood and rope exclusively for the 12 feline residents of the Cat Colloquium. It was the dream of benefactor Wendy Culp to provide this safe and restful space for community to come together for conversation and learning, all in the company of a dozen cats. I find the executive director, Laura Wilson, surrounded by kittens and mousers, with names like, Tuckahoe, Hilda, Buster, and Nellie Belle.

She speaks of the facility’s mission, “We teach diversity, and responsibility through animal care.” The scene is akin to a preteen slumber party after the adults have gone to bed, and all the kids are running around getting into things. Every time I turn around, a different cat is curled up in my camera bag. These are all rescues, not up for adoption, and if you believe in reincarnation, this might not be a bad place to land. Wilson says the Colloquium’s motto is, “There’s no thinking outside the box.” Hopefully, nothing is.

Michigan born, Georgia educated, Samantha Arrow had a legitimate reason to visit Chestertown…her parents retired here. She put her art school education to good use, opening Walnut & Wool, a furniture, clothing, and gift shop on High Street. For two and a half years she’s been refinishing furniture, finding a solid piece with good bones, and a nice shape, then painting it to make it custom. She thought she would sell clothing to the Washington College students exclusively, but it turned out her customers range from 15 – 85 years old. She also loves how vintage clothing always finds it owner. “One time I had a jumpsuit on a mannequin. It could only be worn by a tall, skinny woman. And this tall, skinny woman walked in. I said, ‘You have to buy this.’ And she said, ‘I know.’”

Bob Ortiz, photo by Jim Burger for Main Street Chestertown.

Transplanted artists are nothing new to Chestertown, and finding them isn’t difficult – metal, directional, “ART” signs are all over town. I follow one to the delightful studio of Robert Ortiz. He’s a self-taught, contemporary furniture maker, working in the Shaker and Japanese traditions. He moved here from Baltimore 24 years ago, and likens the time there as the proverbial small fish in a big pond. “Baltimore was a glass with no bottom. Here I was the PTA president for seven years. The scale of this place really makes a difference.” He has put his mark on Chestertown too, building a tea house for a Japanese tea ceremony on High Street as a response to the horrors of the 9-11 attacks, or holding one-on-one workshops for aspiring woodworkers, “I want them to live in my world for five days.” Tempting. Very tempting.

One of Chestertown’s best-kept secrets? It’s an art and culture hub on the Eastern Shore, with numerous galleries to live theater. Carla Massoni is owner of The Massoni Gallery, one of town’s driving forces. Photo by Jim Burger for Main Street Chestertown.

If there’s one overarching theme in Chestertown it’s the art galleries. I visit some with names like, Create, Studio S, Kaleidoscope, and RiverArts. The Massoni Gallery is Carla Massoni, and she’s a force. Thirty years ago Massoni arrived in Chestertown via Annapolis, New York City, and Washington, DC, and bought the Imperial Hotel (home of The Kitchen at The Imperial). She confides in me that owning the hotel was hard work, so she opened a gallery to bring herself some joy. In the ensuing decades she founded the First Friday celebrations (still ongoing today), ushered in new galleries, encouraged artists, and helped build a community. “I’ve formed wonderful relationships with artists, that’s been the payoff for me. Community saves us all.” I tell Massoni some refer to her as the unofficial mayor. She does not demur, “That’s because I love this place so much.”

When I leave Chestertown, I pack my car and drive down Maple Avenue. On the seat next to me is a box containing a couple Sun Buns, I want my wife to taste them. As I cross the Chester River Bridge, I look in the rearview mirror. Chestertown disappears, and like suddenly waking up from a dream, everything is vivid for a moment, then slowly fades away. I enter Queen Anne’s County and drive for a couple miles before pulling off on the side of the road, next to a cornfield. I open the box and eat one of the Sun Buns. Those things always take me back.


  • Melinda Bookwalter
    October 18, 2021 at 9:06 pm

    What a delightful article, thank you! With words you have painted Chestertown with its many charms

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