Since 1977, when Maryland Governor Marvin Mandel officially established the third weekend in May as Kent Island Days, the Kent Island Heritage Society has hosted an annual celebration of their hometown’s s historical and cultural significance.

Kent Island claims recognition as the third oldest permanent English settlement in our country, predated only by Jamestown, Virginia and Plymouth, Massachusetts. It is also the biggest island in the Chesapeake Bay, and being centrally located in our country’s largest and earliest explored estuary, it has played a long and compelling, if too often overlooked, role in history.

In its early days, The Isle of Kent, as founder William Claiborne named the island when he founded his settlement in 1631, provided excellent shipping opportunities during the massive 17th century fur trade, and was a colonial crossroads on the bay. Kent Island’s Christ Church Parrish is Maryland‘s oldest active religious congregation.  Our nation’s earliest charge of piracy was a result of the conflict between Virginia’s Claiborne and the forces of Maryland’s Lord Baltimore, and it is said the first boat built entirely of wood indigenous to the Chesapeake Bay, The Long Tayle, was built on Kent Island. For almost 100 years, nearby Kent Narrows was one of the primary centers of the immense Chesapeake Bay oyster packing industry, and every summer during the age of the grand Chesapeake hotels, Kent Island’s Love Point Hotel was a revered steamboat destination for hundreds of thousands of vacationers and daytrippers .  Today, the Bay Bridge connects Kent Island and the Eastern Shore to all points west.

And Kent Island, just like the entire Eastern Shore, has a unique cultural heritage made up of special people, places, and things.

For example:

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PEOPLE: At the age of 10, James E. Kirwan, born in Baltimore in 1848, was already working as a bay-faring cook and cabin boy, and by the time he was 16 he was the captain of his own schooner. Among his other callings, Kirwan was an entrepreneur, an officer of the Maryland Oyster Navy (where he claimed to have caught more illegal dredgers than any other officer), and a state senator. Known as Kent Island’s Grand Old Man, Senator Kirwan’s home, general store (which he opened when he was 20), and farm were intrinsic to the lives of island residents for decades. One hundred years ago, during the spring and summer of 1917, Sen. Kirwan led a delegation of Islanders in resisting the federal government’s plans to build a military training base and ordnance testing ground on almost the whole of Kent Island. Kirwan passed away in 1938 at the age of 89.


Mary Catherine Kirwan graduated from Stevensville High School in 1930. Despite the protest of her grandfather, the esteemed Senator Kirwan, Catherine attended Chestertown, Maryland’s Washington College, at a time when higher education for women was envelope-pushing.  Insisting on maintaining her independence, Catherine never married, though she did have a longtime companion. She was a bulldozer for the common good and an advocate for many community projects and undertakings, including the Kent Island Heritage Society and the formation of the Kent Island Volunteer Fire Department. Catherine died in 1994. The Kirwan House and Store Museum, located in Chester, is now a living history museum, recreating a country store of the early 1900’s, and is open the first Saturday of each month from May to October.

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Julius Grollman was born in 1920, and was the son of Henry and Lena Grollman, who immigrated to America from Lithuania. Following in his father’s mercantile footsteps, Jules as he was known to most,  operated his family’s hardware/liquor store for decades. Jules served as Queen Anne’s County Commisioner for 12 years, was a charter member of the KIVFD, and a member of the Temple B’Nai Isreal in Easton, MD.  Jules is a pivotal character in the nonfiction book Wye Island: Insiders, Outsiders and Resistance to Change, Boyd Gibbons’ classic story about a rural community (specifically this particular rural community) waging war against outsiders and over-development.


My dad’s grandfather, Joseph Coleman, exemplifies the Eastern Shore of the 1920’s: boats, farm clothes, and hunting dogs. Joseph Coleman died while crabbing on Tuesday, August 31, 1937. He’d left home around 4 a.m. and his empty boat was found by his son Paul and another crabber around 11, his crab lines still wet and intact. A large search party was formed and though great-grandfather Coleman’s body was not found that day, his body was discovered on Wednesday, about 24 hours after he probably died. A large gash was evident on his forehead, and it was determined he’d cut it when he fell overboard while trying to remove seaweed from his boat’s propeller. The Queen Anne’s Record Observer newspaper said that Joseph Coleman “made his home on Kent Island for many years, where he was one of the most highly respected citizens.” Joseph Coleman was survived by his wife, “who was Miss Addie Timms,” as well as five sons and six daughters, including my grandmother Ella.

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Wally Dashiell was a young German classical dancer during World War II. As a postwar American wife and mother, Wally taught ballet, jazz, tap, and character dance to children for over six decades. She’s a multi-gold medalist Senior Olympian in Track and Field, and won the first ever Queen Anne’s County Chamber of Commerce award for outstanding volunteerism.  She’s a breast cancer survivor, green thumb gardener, needlework craftsperson, and crossword enthusiast. She’s thrown out the first pitch at an Oriole’s game and in 1996 was honored to be one of the Marylanders chosen to carry the Olympic torch.  She is a member of the Maryland Senior Citizen Hall of Fame and in 2004 was inducted into the first class of the Maryland Senior Olympics Hall of Fame. As a distinguished member of Maryland’s dance community, Wally is a past president of Dance Masters of America regional chapter and the Ballet Theater of Annapolis. A life member of the Maryland Council for Dance, Wally served as their faculty chairman for 20 years. She’s also been a board member for the state arts council. Ninety-nine years old now, Wally Dashiell has been a perpetual whirlwind of activity and is a beloved Kent Island icon.


PLACES: In the early part of the 20th century, upon disembarking at the The Love Point Hotel’s 1,250 foot long pier, new arrivals to this Chesapeake Bay resort were treated to the scenic view of the hotel grounds: a sandy beach, expansive lawns and picnic groves dotted with cottonwood trees, a lake with canoe rentals, an amusement boardwalk with a merry-go-round, a bowling alley, and a shooting gallery.  Closed around 1947, the Love Point Hotel sat abandoned and vandalized until a 1965 blaze ended the hotel’s physical existence, if not its sentimental and nostalgic stature, even in the imagination of those not old enough to actually remember its eminence.


The first town on Kent Island, Broad Creek, has mostly been lost to the passage of time and tides. There are now two distinct areas of Kent Island: Chester and Stevensville. Stevensville (the zip code) includes everything south from Love Point to Kent Point and east from Bayshore to Cox Creek, and Chester covers everything from Cox Creek to Kent Narrows, the small body of water separating Kent Island from the mainland Eastern Shore.  Stevensville (the town) was developed after construction of a nearby church and the sale of two farms in 1850.


According to the Historic Sites Consortium of Queen Anne’s County,  the little shot-gun-style Stevensville Post Office, first noted on an 1877 map of the town, served as a “gathering spot for townspeople to share news or pass the time” for decades. The building was acquired by the Kent Island Heritage Society in 1997. “Gold in color, gable end to the street, and trimmed with white gingerbread eaves,” the Old Stevensville Post Office serves as the Kent Island Heritage Society’s headquarters. (


Cray House, “One of the most unique structures on the Eastern Shore” is a National Register site located on a tract of land once called Steven’s Adventure, and granted to Francis Stevens in 1694. Built around 1809, the Cray House is a rare example of post-and-plank construction. The house was sold at public auction in 1914 and was lived in by Nora Cray, a widow, and her three children. In 1975 her heirs donated the property to the Kent Island Heritage Society, who have restored and furnished this treasure.


The Stevensville Bank of Maryland building was completed in 1909 and for fifty years was the financial center of Kent Island. Surviving everything from the Great Depression to the construction of the Bay Bridge,  the name of the institution was changed to The Tidewater Bank in 1960, and with the name change came a new location. The downtown building that had served the banking community for so many years was now the offices of The Bay Times, Kent Island’s new hometown newspaper. After a few years of intermittent vacancies after the paper moved to new digs, the building was leased to the Kent Island Heritage Society by the current owner for $1.00 per year. The Old Stevensville Bank has been refitted to reflect it’s look from the early 20th century, and the building was placed on the National Register of Historic Places in 1983. The Old Stevensville Bank now serves as a small museum and gift shop.


In the era of the steam train, the Stevensville Station was the first railroad stop out of Love Point. After the completion of the Bay Bridge, the trains stopped running and the station was left vacant. It was donated to the Kent Island Heritage Society, who restored to show what a visit to the train station might be like for travelers of that simpler era.  The caboose, originally built in Baltimore between 1924 and 1929, was utilized as office space in Millersville, MD after it’s retirement, and was donated to The Kent Island Heritage Society in 2006.

And though our reputational image here on the Shore consists of such THINGS as boats,



and the Bay Bridge,


Around here, we’re really mostly about things like heritage and history; hard work, hospitality, and a sense of humor.


Kent Island Changes Name to Bermuda to Attract More Tourists! April Fools Day, 1965!


This year’s Kent Island Day festivities will take place on Saturday, May 20th in downtown Stevensville. The traditional Main Street parade kicks off the daylong event at 10:30 am. Afterwards, the community fair that follows will feature fun for the whole family, including entertainment, children’s attractions,  and food vendors for every taste. All of the historic sites in the town of Stevensville, such as the train station, post office, bank, and Cray House will be open to the public, and historical reenactors will both entertain and educate. easternshorebrent, will be there too!

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