Mackey Dutton: Setting Her Sights on a New Season By Lisa J. Gotto

It’s a typical hot and muggy late summer afternoon in Chestertown. The type where there are generally few people milling about High and Cross Streets, and if people are outside, they’re looking not to stay out very long.

There is, however, a small group of residents beginning to gather at Wilmer Park around 4 p.m. They are among the precious few at the park at that time. Recent drenching rains have made the grass thick and dense-feeling even under a shoed foot. One member of the group stands out from the rest — remarkably unphased with the condition of the grass even though she is navigating it in her bare feet.

For those who know her (and quite frankly there are relatively few in town who don’t) this sight is a common occurrence at the park.

On September 1, the first pallino will drop on the Fall 2026 Ye Olde Bocce League season in Wilmer Park, and Chestertown native Mackey Dutton will be there with bells on and shoes off for her 13^th year of playing on team Ten Commandments.

Mackey and a dozen or so of the league’s most zealous team players were out that muggy afternoon not just because they are preparing for that first September match, but because these lovers of the game practice and play all year long.

A lively competitor, at 96 years young, bocce is just one of the activities that Mackey enjoys regularly. Attend any of the various local events or social occasions taking place within our town limits at any given time and you will likely find her surrounded by a coterie of residents and friends engaged in a lively conversation about town topics, books she’s reading, what’s going on with her Questers club, or dishing the tea about the outcome of last week’s bocce match up.

Like many babies of the era, Frances Mackey Metcalfe was born in Philadelphia in 1930, as Chestertown did not have its own hospital until 1935.  As she tells it, her life here as a child was filled with family-centered adventures, as both her mother and father came from large families (at least 6 kids on each side). So, there were many cousins to play with and life along the river provided the simple joys that are most commonly realized as joys only when we are older.

“I was never in a swimming pool until I was 15,” she avows. “We just all swam in that river.”

Back then, Mackey says, Chestertown was best-known as a place where everyone knew everyone else, and where a mischievous child was quickly reported on by one elder to another, which resulted in fewer mischievous children.

“This was a wonderful town to grow up in,” she says.

Residents of the era worked on its nearby farms, at the pickle factory, and even at her father and uncle’s grain and feed business. Her family settled on Water Street, and they would be associated with that address for several decades.

As many residents of current-day Chestertown already know, various branches of the Metcalfe and Wilmer family trees resulted in civic and business leaders who were instrumental in the growth and even management of the town. (Her uncle, Philip G. Wilmer was the town’s long-serving mayor in the mid-20^th century, and her father, Jim,  and several uncles helped found the Chester River Yacht & Country Club.)

These familial experiences, stories, and enterprises are woven like the threads into the fabric of the community quilt of sorts that is Chestertown; a quilt that is colorful and stitched with lore. As such, Mackey is often tapped when a conversation veers into a historical lane. Blessed with an amazing memory, Mackey fondly recalls the sounds of the “tomato boats” that were loaded up by the bushels-full at the foot of High Street to be transported to Baltimore for manufacturing. The taste of a Bell Haven Baked Tomato still lingers with her (the original recipe hangs in her kitchen) and the thought of the popular Sophie Fisher Inn, a prominent rooming house once located at the corner of Maple Avenue and North Queen Street, evokes a sense of nostalgia.

While she would leave Chestertown for Cincinnati after marrying her first husband, Don, they would later return after having three children. While that marriage would end in divorce, Mackey would find her way back to Water Street where her mother, Frances, was still living. She would clandestinely meet Fred Dutton at a local wedding and marry again a few years later. Together they would steward the restoration of the historic Bolton House on Queen Street, where they would host fabulous parties and where she would continue to live after Fred’s passing in 2008, and up until 2017, adding another intriguing chapter to the resilient book of her life.

No stranger to hardships, Mackey would lose her precious daughter, Paige, to melanoma in 2013 at the age of 58.  “It runs in families,”  she conveys.

And for a time, last year, that reality would hit home again when she was diagnosed with the same condition affecting her right thumb at the age of 95. Her Annapolis oncologist wanted to schedule surgery to remove a portion of that thumb as soon as possible.

But Mackey knew this would mean some down-time in September for her and her reliable throwing hand.

Her reply to the oncologist was, “But this is bocce season. It’s going to have to wait until November.”

“The doctor just shook his head and said, ‘I’ve heard a lot of reasons [to delay surgery] but that’s the first time I’ve heard that one,’” she muses.

Needless to say, Mackey was back out and practicing (in her signature barefoot style) as soon as she got the post-operative green light. Undaunted, she would re-train her hand to operate regardless of that missing portion of thumb.

“And I’ve learned to throw [the ball] fairly on target!”

This season you can catch Mackey back on the field at her Uncle Phil’s namesake park and perhaps afterward at one of her favorite neighborhood haunts enjoying a loaded cheeseburger sans hot peppers and mustard.

“So, I started drinking beer at the Bluebird [Café] in 1947 when I started college,” she waxes poetic.

“And I have yet to be carded.”