God Bless Us (and everyone)

God Bless Chestertown

(and everyone) 


by Rafael Alvarez 

As the circus proprietor Sleary declares in the Charles Dickens’ novel Hard Times, “People must be amused …”

And, just before this past Christmas, tourists and locals in Chestertown were thoroughly entertained by “A Dickens of a Christmas,” an annual pre-holiday fair on High Street, affirming Sleary’s observation that people “can’t always be a working…’” 

Nope, not when there are bagpipers in the street, shop windows decorated for Christmas in the sugar plum style of 19th century London, ladies and gents clomping around on stilts and horse-drawn carriages on the road that runs by Stam’s Luncheonette, the White Swan Tavern and Bee Crafty Collectibles.  

“It gains momentum every year, a place where families like to gather for the holidays,” said Jeff Maguire, owner of Zelda’s Speakeasy, a saloon around the corner  at 108 Cross Street. The popular tavern is just a few doors away from the Bookplate, a world-class bookstore where you are as likely to find works by Nobel laureates Modiano and LeClezio as you are Margaret Mitchell and Laura Lippman. And a black cat named Keke.

A colonial rivertown of some 6,000 people, Chestertown was founded in 1706, more than a century before Dickens’ birth in Portsmouth, England. It boasts the second largest collection of restored 18th century homes in Maryland and is the site of Washington College, which dates to 1782.

And the Chesapeake Bank & Trust, in front of which the Flying Flea Circus and Wahoo Medicine Show pitched its tiny tent during the Christmas spectacular.

Humbugs, you say? A bamboozle?  Why child, you cut me to the quick! These are world-renowned professional aerialists under the tutelage of ringmaster George Esparza of Bethlehem, Pennsylvania.

Esparza brought his marquee performers: Jacques Fleaoque, world record holder for a high dive by a flea, leaping from a miniature hot air balloon into a gerbil dish of water; the recently retired Boris the Great, who once did backflips on the rump of a large dog in Moscow; and the star of the show – Napoleon, the world’s fastest flying flea.

“I performed on a wonderful, unseasonably warm evening – there were good crowds all weekend and with people in costume and horse-drawn carriages you could actually feel like it was the 19th century,” said Esparza, noting the beauty of the town. “All jingle bells and the smell of good food.”

And, of course, Santa Claus, who arrived upon a Chestertown Volunteer Fire Company ladder truck over the Thanksgiving weekend to launch the festival and the season.

Year round, folks from up and down the East Coast and as far away as California and the Hawkeye State arrive in Chestertown by bicycle, boat, and car. There’s a public airport 20 minutes away in the town of Massey.

Visitors come for live music; cruises on the River Packet, a  1920s style touring yacht; fresh seafood – the linguini with scallops and shrimp at Luisa’s Cucina Italiana is superb – and, on weekends between the end of the year and spring, an open-air market on High Street for produce and artisanal goods.

So let’s say it’s sum-sum-summertime and you buy some aronia berries from Molly and Roy Mears, who grow and harvest the mouth-puckering, antioxidant fruit on their farm not far from Chestertown.  

You take them home and want to rinse them. Master potter and market vendor Doug Sassi (ask him about seeing Jackie Robinson play ball in Ebbets Field once upon a time) can help you out with a ceramic colander.

Local farmers sell fruit and vegetables on High Street and Fountain Park alongside it all year-round on Saturdays. The artisans will return in Spring.  

You want old school Chestertown steeped in nostalgia but not headed for the Historic Register anytime soon? Proccolino’s Pizza has been feeding families, students and Little League teams for more than 40 years. Then you can wash it down with a milkshake from The Freeze, an independent ice cream stand at 717 Washington Avenue, home of the “Big Freeze Burger.”   




Many of the stories for which Charles Dickens is famous (he was known as “the inimitable”) were puzzled out as he took long walks throughout London and the nearby countryside. It is said that with his “swinging gait,” he regularly walked 20 miles or more each day.

A good hike can take you from Stam’s – a converted 19th-century apothecary that would be at home in Dickens’ The Old Curiosity Shop (1840) – to waterfront trails along abandoned rail lines south of town.

Along the way, you will pass Wilmer Park and a stunning stainless-steel and grass berm sculpture – Broad Reach – by Baltimore-based artist David Hess.  The work is dedicated to Alex Castro, an architect, artist, and long a champion of the arts in Chestertown now living in Florida.

Others just stroll from one end of High Street to the other and back again, eating ice cream, sipping coffee, perhaps daydreaming about why everyday can’t be so serene. 

This past summer, as teenage boys skateboarded in Hogan’s Square before storm clouds rolled in (canceling that evening’s Steam Packet cruise), native Iowans Sydney Schreiber and Michael Thompson took a short drive into town from Queenstown, which sits on a creek of the same name off of the Chester River.

There, they were visiting relatives and checking crab traps at the end of the pier for Big Jimmies and decided to visit Chestertown just to pass the time and enjoy ice cream, a table on the sidewalk and a strong, clean breeze off the river. 

Whether from Iowa or Ireland, all you have to do is find your way to the sublime Eastern Shore of the Old Line State.

“Chestertown is a place of people who grew up here, people who chose to make it their home and business owners who see it as a good investment,” said Nina Fleegle, executive director of Main Street Historic Chestertown. “We live in a historial, cultural, artistic and environmental gem. It speaks to my soul.”


Rafael Alvarez is the author of the Orlo & Leini tales. He can be reached via patreon.com/rafaelalvarezbaltimore 



  • No comments yet.
  • Add a comment