Not so long ago, the idea that a woman would be attending the United States Naval Academy would have struck many of a certain age as unimaginable, but when Gunston School senior Sydney Nittle was asked how she felt about attending this historically male institution, she had a look of surprise in her eyes that suggested how silly that question was in 2021.

So it is so refreshing to note that for this generation of high school seniors, that antiquated debate regarding single-sex education in our military academies is ancient history.

But what is even more refreshing is the exceptional quality of candidates that places like West Point and Annapolis are attracting even at a time when the United States remains engaged in combat operations.

A case in point is Gunston School’s Sydney Nittle. Motivated by a family history of military service, the active support of the Mid-Shore’s Bob Degour, the volunteer USNA Blue and Gold officer who helps future midshipmen with Academy admissions, and Gunston’s focus on developing leadership in their graduates, the stage was set for Sydney to navigate the extremely difficult application process and successfully become this summer an official member of the Class of 2025.

We asked Sydney the other day to stop by the Spy studio to talk about that process as she prepares her summer enrollment in Annapolis in a few weeks.

This video is approximately four minutes in length.

For close to four centuries, the Mid-Shore has debated the pros and cons of “Come Heres” by the “From Heres.” Harking back to when white settlers were starting to arrive in Maryland in the 1600s, there has been a longstanding caution by those born in the five-county region to outsiders moving into their communities.

While this historic impulse is now mostly the subject of good humor, the dynamic can still have an edgy side when it comes to politics, culture and the inevitable impact on home values and property tax assessments.

But to its credit, the Mid-Shore is also well aware of the extraordinary positives that come with the “new” people. And one of those clearly in the case of philanthropy. With such extraordinary examples as the W. Alton Jones family and more recently, the late Jim Clark, generations of “Come-Heres” have been instrumental in the creation and ongoing support of museums, schools, hospitals, and countless other civic needs.

That’s important information to remember as the Eastern Shore experiences an unprecedented surge of Come-Heres, well, coming here. Even before the COVID pandemic fundamentally changed both life and work for many, the Mid-Shore, with its proximity to three major American cities, was seeing a wave of former urbanites calling Dorchester, Kent, or Talbot Counties their primary home of residence.

One of those new “Come Heres” is Bill Ryan. A native of Pittsburgh, Bill makes no secret that he has come from a very privileged background. The grandson of a mining engineer who made a fortune inventing the first hardhat with a light built into it, Bill has enjoyed the kind of upper-class life that included private schools, professional success, and such recreational pursuits as sailing.

And sailing was a major co-factor in Bill and his wife moving to Talbot County eight years ago. Both long-time professors at Penn State, the semi-retired couple were not only eager to enjoy life on the Chesapeake Bay but also to give back to the community.

In his Spy interview, Bill talks about his roots, his family’s influence in wanting to give back, and his unique role as Chair of Building African-American Minds (BAAM) in Easton.

Following in the footsteps of Clark, Bill Hunter, and Dickie Firth, Bill was keen to support the work of founders Derick and Dina Daly with capital investments to expand programming, the building of an athletic center, and now heading up a capital campaign for BAAM’s new academic center.

The Spy spoke with Bill at the Spy Studio a few weeks ago in Easton.

In a few weeks, Americans of all sorts will be celebrating the traditional Memorial Day weekend. And in between family BBQs and trips to the beach, many of them will attend ceremonies or parades that honor those who have died while serving in the military for the United States of America.

One of them will be Chestertown’s Michael McDowell. With long ties to the military, the Irish-born retiree quickly connects to America’s servicemen and women when reporting for the CBC, being a scholar at Harvard, or while serving The Citadel’s board of directors. His enthusiasm was so positive that he nor his wife, Susan, thought twice about their son attending a military academy nor a future career as a Marines.

But Memorial Day has meant something entirely different for the McDowells since they received word that their son, Conor, their only child, was killed in an planned military exercise accident in California two years ago this month.

Conor, who had only recently graduated from college, was training in an armored vehicle with several others when it unexpectedly fell and rolled into a exceptionally large crevasse in the practice zone.

It is impossible to comprehend the loss of this magnitude on any parent, but for Michael, the pain was so much more intense once he discovered that Conor’s death could have been entirely avoidable.

After flying out to California to comfort Conor’s fiancé and meet with officers about the tragedy, a simple Google search told the veteran journalist that his son’s accident was just one of a long pattern where men and women were dying during similar rollover accidents.

That search result was all that was needed for the McDowell family to transition from profound grief and turn it into a campaign. Using long established Washington contacts and the support of the Maryland delegation in Congress, the McDowells did something that is rarely done in the federal government; as private citizens they convinced the Government Accountability Office (GAO) to launch an independent review of military training and oversight. The GAO will release that study and its recommendations to Capitol Hill next month.

The Spy talked to Michael at his home in Chestertown last week about this painful journey and the special mission of truly memorializing his son Conor.

This video is approximately six minutes in length. 

With news that President Biden plans to overhaul the Northeast Corridor Amtrak railway system with an infusion of $80 Billion as part of his infrastructure proposal, it was good timing to meet historian and author Lorett Treese and learn about the history of railroads on the Eastern Shore. 

Even if the infrastructure plan prevails, however, the Eastern Shore will never see another golden era of railroad transportation, and except for a few small spurs still operating, railroad history will languish on the shelves of museums or found piecemeal as artifacts like the 1902 Chestertown train station.

Treese, who holds a master’s degree in American History from Villanova University, spent twenty years as a Bryn Mawr archivist, and has long had a fascination with railroads. Three of her books describe a complicated growth, countless changes in rail ownerships (and names), bankruptcies, mergers, buyouts, and blue-sky dreams that never materialized as railroad companies large and small tried to connect

In her newly published Railroads of the Eastern Shore (The History Press), Treese writes an extensive history of the Delmarva Peninsula’s many bids to create north-south rail lines between the Eastern Seaboard and Norfolk, Virginia via a line southward through the Shore to Cape Charles, 60 miles south of Chincoteague.

The America of the early 19th-Century sought a faster and more reliable transportation system than the rough overland stagecoaches, canals, and steamships. As early as the 1830s, plans were made, and State “charters” were given to independent railroad companies to connect the Shore with mainland markets. Most of the rail lines were never built but exceptions like the 16-mile railroad New Castle and Frenchtown Railroad was completed in 1832. 

 Treese says that the earliest evidence she found for an Eastern Shore railroad was an 1833 plan for a rail line that would have run from Elkton to Tangier Sound near Crisfield. “Unfortunately, it was one of the many, many chartered railroads that were never built. It would have been called ‘The Eastern Shore Railroad,” and would have been the first of the railroads to bear that name.” 

Planned for decades and interrupted by the Civil War, it wasn’t until the 1880s that a north-south railroad was finally built to traverse the Eastern Shore.

The New York, Philadelphia & Norfolk Railroad carried freight and passengers to a steam ferry connecting Cape Charles and Norfolk. Eventually, the massive Pennsylvania Railroad acquired the line. This system and an ever changing network of “feeder” lines connecting towns on the Shore endured almost a century. 

The building of the Bay Tunnel Bridge and the Chesapeake Bay Bridge in the 60s brought the rail system to a close. Aside from the Amtrak station in Wilmington, DE, still connecting the Northeast Corridor, Baltimore, and Washington, only a few small feeder lines continue to operate in the region.

Lorett Treese’s book is a great lesson in historical explication: her three years of research uncovered original documents clarifying the intricate puzzle of rail plans and ownerships. She employs a clear narrative to document the story. Even if you are not a railroad buff, the story holds interest for its portrayal of American commerce and its effort, failures and successes 

The historian tells the Spy that many of her historical discoveries were gleaned from rummaging through countless cardboard boxes found in the Pennsylvania Archives, Temple University, and Hagley Museum and Library in Wilmington, to name a few.

“The old records of the Pennsylvania Railroad were split up, but The Hagley had the records of the subsidiaries I wanted, including the NYP&N and the PWB, and none of that stuff is online or microfilm. It’s in big cardboard boxes, and I would go down a couple of times a week, and I would say, give me box number this, this, and this, and I would take out the files one at a time and look at every piece of paper.”

Only vestiges of the railroad era remain today—a restored station here, a small museum there— but for a century, the iron-horses and diesel locomotives were an integral part of the transportation landscape. Still, a few local connector trains will trigger flashing red lights and bring down a crossing gate to stop highway traffic.

“Trains are still running on the old Kent County Railroad, thanks to its modern-day successor, called the Maryland and Delaware Railroad but only as far as Worton. Originally, the train traversed the Shore form Chestertown to Woodland Beach (Smyrna) Delaware where it met steamboats from the Delaware City, Salem, and Philadelphia Steamboat Company.

For us, the 117-year old Chestertown passenger station—and the short run in Worton— remain our only link to the Shore’s railroad past.

Treese writes, “At the base of Chestertown’s Cross Street, there’s a passenger station built circa 1902-03, a time when the Kent County Railroad had been liberated from its New Jersey connections to come under the control of the Pennsylvania Railroad.”

Lorett Treese’s other books include, The Storm Gathering; The Penn Family and the American Revolution, Valley Forge: Making and Remaking a National Symbol, A Serpent’s Tale: Discovering America’s Ancient Mound Builders, Railroads of New Jersey, and Railroads of Pennsylvania. She has also published widely in magazines. 

This video is approximately eight minutes in length. Railroads of the Eastern Shore may be found on Amazon and at historypress.com.

Spy readers may remember the name of Neil King from a few months ago when he generously contributed a masterful treatment of Frederick Douglass and the historic landscapes of the Eastern Shore. But he is best known as the well-respected global economics editor for the Wall Street Journal, who now calls Claiborne, a hamlet a few miles east of St. Michaels, his weekend home, where he works on independent projects that capture his imagination. 

So shortly after he completed one of those projects for the Spy, he fulfilled a long-term aspiration this spring by opening the front door of his house in Washington, D.C. one morning and walking to the heart of Manhattan over the next 26 days.

There were several motivations for this particular journey. Neil had wanted for some time to retrace the steps of many of the founding fathers in the 18th Century who were required to make similar trips between the new country’s northern and southern regions. He also thought the experience would make an interesting book that continued the tradition of such travel writers as de Tocqueville and Dickens in documenting Mid-Atlantic America. 

But what King didn’t anticipate during this leisurely stroll (he stayed at B&B’s and hotels along the way) through Maryland, Pennsylvania, and New Jersey was how his daily encounters with “real Americans” would result in what he could only describe as a religious experience. For it was not only the sense of connection with people who were so different from his own background and political beliefs but how stunning and meaningful this old pathway had become for him and his hopes for America’s future  

The Spy sat down with Neil at the Claiborne Village Hall last week to talk about that experience as he prepares to collect his journals, images, and thoughts for a book we can hardly wait for. 

This video is approximately ten minutes in length.

Not that long along, Dominique Sessa had set her sights on being a dancer. As a child, she loved to dance, and her dreams of finding a career in that field seemed quite natural given her ample supply of self-determination. But a freak accident when she was 13 years old changed her life forever, including her transition from ballet to being a leading advocate for the disabled in the State of Maryland by the time she had turned 25.

That childhood accident would turn out to be the earliest sign of a rare and progressive neuromuscular disorder that would eventually rob her of the use of her legs. While it was hard to detect at first, Dominique’s condition would eventually lead her to move to the Eastern Shore and the particular health care for her condition only available in Salisbury.

This life journey would be a profound challenge for anyone so young, but for anyone who knows Dominique Sessa, it comes as no surprise that she has not only been able to cope with her disability but almost instantly rise to be a lead advocate for those on the Eastern Shore, a region that has historically been without a voice in city government and more recently the state of Maryland.

Last year, Governor Larry Hogan appointed Dominique to be a member of the Maryland Commission on Disabilities. Not only is she one of the youngest members to serve, but she is also the only representative of the Eastern Shore.

In her Spy interview, Dominique talks about the unique needs of the disabled in such a rural environment as the Shore. She also talks about the need for frank and honest conversations between the general public and a growing number of citizens who must navigate in a society that still finds it awkward to ask questions or actively listen to those with special needs.

This video is approximately five minutes in length. For more information about Dominique Sessa  work please go to her website here.