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This is a free excerpt from my book, Eastern Shore Road Trips #2: 26 MORE One-Day Adventures on Delmarva. More info here about that and my other books exploring the history, travel, and culture on the Eastern Shore and in Delaware.

Every year, millions of travelers looking to get away from their busy big-city lives catch their first glimpse of the Delmarva Peninsula in the shoreline of Kent Island. That view from the Chesapeake Bay Bridge can be quite the powerful experience, judging by how many times over the years I’ve heard folks marvel at the way their stress levels ease the moment that Eastern Shore comes into view. 

Kent Island is indeed a sweet, scenic destination, but there is a bit of irony in this, considering how much stress and contention the people of the place have endured over the centuries while trying to defend their turf against one set of invaders after another. The identity of those enemy hordes is interesting: First came Marylanders; then came the federal government; and then came all those tourists across that bridge.

In the Bitter Beginning

Kent Islanders have every right to have a chip on their collective shoulder. Across the Chesapeake Bay in Southern Maryland, historic St. Mary’s City sucks up all the tourism and media attention that goes with being the founding settlement of the Free State. They have the living history park. They have the replica sailing ships. 

In point of fact, however, the first permanent settlement in what would become Maryland went up here on Kent Island, on the horizon that comes into view to the south while crossing that bridge from the western shore. William Claiborne explored the waters out that way in the 1620s, armed with a license from the British crown to trade with Indians under the auspices of Jamestown and its Virginia overlords. He used that authority to buy Kent Island from local Indians. 

Then, in 1631, three years before the famed Ark and Dove sailed into St. Mary’s City, Claiborne brought some 100 men onto Kent Island, where they put up a fort. The island has been home to Europeans and their descendants ever since. 

Everything looked quite promising for Claiborne’s venture until folks back in England changed the rules in the middle of the game. In 1632, King Charles I signed a charter awarding all Chesapeake lands north of the Potomac River to George Calvert, aka Lord Baltimore. This development pushed Claiborne’s Kent Island out of Virginia and into the new Terra Maria, named in honor of Queen Henrietta Maria. 

Claiborne raised quite a ruckus. The first skirmishes were legal affairs, fought by way of petitions arguing over this clause in Claiborne’s license versus that one in Lord Baltimore’s charter. Things got physical soon enough, however, with battles breaking out between newbie Marylanders and Claiborne’s Virginians. In the midst of this, Claiborne sailed back to England to confer with business partners and file more legal claims. Alas, the guy he put in charge in his absence waved a white flag, surrendering the island to Maryland.

Next came the crazy days that historians refer to as “The Plundering Time.” A furious Claiborne sailed back and re-conquered Kent Island. Meanwhile, a cantankerous bunch of Puritans who couldn’t stomach life under the Catholic Calverts took the whole Maryland colony by force. Back in England, Charles I was losing his head, quite literally, on charges of treason.

Three often bloody years later, things got sorted out with Maryland back in the hands of the Calvert family. Claiborne remained bitter about this turn of events for the rest of his days. Just before his death in 1677—three decades after “The Plundering Time”—he was still filing paperwork with the king, claiming that Kent Island rightfully belonged to him. 

Cross Island Trail on Kent Island

Walking the Cross Island Trail

No physical remnants of those Claiborne days remain today on Kent Island. In all probability, the settlement he built was on land that is now under water. The best way to get a feel for the landscape in that general area is by heading south on pretty Romancoke Road, where you can take time to stop at little Matapeake Beach and stroll or bike along the South Island Trail that runs parallel to the road for six or so miles. 

The closest you can get to the old fort is along Kent Point Road, which angles off to the right. There is no place to stop or markers to see that way, so take that drive only to enjoy a pretty run of farmland and waterfront mansions that ends in a little watermen’s enclave. If you stick with (or return to) southbound Romancoke Road, it will end at a pretty fishing pier that looks out onto Eastern Bay. Ferryboats running from Annapolis used to stop here in the early 1900s on their way to a Talbot County town called, quite appropriately, Claiborne.

The 20th-Century Invaders

That view of Claiborne presents a sideways route into one of the two more recent invasions that have rolled onto Kent Island. For three centuries after Claiborne put up his fort, this remained a thoroughly isolated outpost accessible mainly by boat, with overland traffic from the western shore relegated to a ridiculously roundabout route that involved circling the top of the Chesapeake Bay at Elkton. 

Eastern Shore Secrets: Opening Day for the Chesapeake Bay Bridge on the Eastern Shore of Maryland

Opening day on the Chesapeake Bay Bridge

That all changed in July 1952, when the Chesapeake Bay Bridge opened for business. That project had quite a bit of support here on Kent Island and all around the Eastern Shore. Many folks liked the prospect of quicker trips to the big cities. They liked, too, that new jobs might arise to serve the throngs of people expected to use the bridge. Business leaders at the beach resorts loved the idea for obvious reasons. 

But strong opposition arose as well. Shipping companies thought the span might present a navigation hazard during storms and fog. Ferryboat companies fought the project tooth and nail. Lots of locals feared that the bridge would bring an end to those old and isolated ways of life. Some local musicians penned a ditty that became an anthem for this anti-bridge crowd (it remains pretty popular today, actually). [A] dance band … got a rise from local partygoers when it played “The Old Gray Mare” to new lyrics. The chorus ended, “We don’t give a damn for the whole state of Maryland/We’re from the Eastern Shore.” 

The most public face of the opposition belonged to state Sen. Henry Balch, who hailed from Talbot County. A lawyer and a World War I veteran, Balch was rightly famous for his colorful way with words: The proposal to build the Bay Bridge is extravagance to the nth power. The spending necessary would exceed the aggregate spending of every drunken sailor since John Paul Jones.

Balch and his compatriots lost this war, of course, though he did fight to the bitter end, filibustering away in a last-minute speech that delayed a final vote in favor of the bridge by a few hours. 

You will see for yourself how things played out. The main drag of Route 50 is mostly a sea of gas stations, fast food joints, and strip shopping centers. Expansive housing developments cover many nearby properties, especially those where the waterfront is within sniffing distance. This is why, when I first moved to the Eastern Shore, I didn’t have much use for Kent Island—my knowledge of the place just didn’t go beyond that highway yet.

Eventually, I got off the main drag and discovered a fun, idiosyncratic destination. As road trips go, Kent Island is a mix- and-match affair. There is no real must-see attraction at the top of the agenda. Instead, you’ll need to sort through a bunch of options and tailor an itinerary to your preferences. 

If you are in a nature-loving mood, for instance, you should stay on Romancoke Road and cross over to the north side of Route 50. Turn left at a light onto Skipjack Drive into an industrial park, then go left again at Log Canoe Circle to find the parking area with access to Terrapin Park and the Cross Island Trail.

A short, easy footpath through the park leads out to a little beach with a cool view of the Chesapeake Bay Bridge. There, you can think about whether the TV show “Inside Edition” was right to name this the “scariest” bridge in the country. Back in the parking lot area, you can hop on the Cross Island Trail, which runs through nearby woods and across little streams for 6.5 miles to Kent Narrows, with a project in the works to extend the trail farther east. 

After that, find your way into tiny downtown Stevensville, which is quite nearby, but tucked away at the intersection of Main Street and Love Point Road. Several antiques shops, a couple galleries, a restaurant, and a bakery were up and running on my last visit. You’ll also find several interesting remnants of times gone by—an old post office here, the old bank there, and an old train station in the back corner of a little park. These are among the host of historic sites in Queen Anne’s County that open their doors for inside tours one Saturday a month—you can check on that schedule through the Kent Island Heritage Society.

Two other buildings here in Stevensville are well worth pausing over. The first, on Love Point Road, is the old Lowery Hotel. Now privately owned, the building dates back to the Civil War. When overnight guests started arriving in 1883, a livery stable was part of the deal. By the early 1900s, facilities like the Lowery were becoming a big deal on Kent Island. At the height of the steamboat era, this was quite the convenient getaway from Baltimore. 

Women Walking at the Love Point Hotel in Stevensville on Kent Island, Maryland

Women Walking at the old Love Point Hotel on Kent Island, Maryland

The most famous of Kent Island’s resorts was the Love Point Hotel, set on the northernmost tip of the island along Love Point Road. It was romantic as all get out, with sandy beaches, elegant porches, and long, lovely lanes perfect for strolling hand in hand. A poem from those days by Folger McKinsey sums things up:

Here comes the steamer, the lovers are here,
Jack with his daisy and John with his dear;
Soft crabs for dinner and oh, what a dream,
Peachcake for supper, and then the ice-cream!
Red roses fair on her cheeks of rose-red,
And these are the words that her true lover said:
“Good-by to the city,
To Love Point away;
The wind’s on the water,
The boat’s on the bay!
From toil and from trouble
Lighthearted we’ll glide,
With lunch in a basket,
A girl at my side!” 

The hotel closed in 1947, just as the state legislature was getting ready to approve construction of the Bay Bridge. You can take the pretty drive from Stevensville up to Love Point today, but the hotel building is gone—it burned in the 1960s—and there is no little park or other place to stop up that way. 

A second building worth pausing over while in Stevensville is the former Christ Episcopal Church on Main Street. The congregation that worshipped here after the building went up in 1880 ranks among the nation’s oldest Episcopal parishes, tracing its lineage clear back to the days of William Claiborne. The gorgeous Queen Anne-style affair has an unusual “lancet” chimney built with wooden pegs instead of nails. 

The churchyard here is where Kent Islanders first marshaled their forces to fight off yet another threatened invasion. With World War I looming in 1917, the federal government decided to buy up the entire island and evict all of its residents. They were going to turn the place into a military “proving ground,” where weapons are tested. 

On the Monday evening of July 9, 1917, local civic leaders convened a meeting at Christ Episcopal that drew an overflow crowd ready to defend its turf. A Kent Island Home Preservation Committee took shape that night, and they soon headed off en masse to Washington, D.C. to press the issue. This is one battle the islanders won in the end. The bombing experiments the feds had in mind eventually found a home at Aberdeen Proving Ground, over on the western shore. 

The Narrows and Beyond 

The Jetty Dock Bar in Kent Narrows

The scene at Kent Narrows

The hero of that 1917 fight was James E. Kirwan, who by the time of his death in 1938 was known far and wide as “The Grand Old Man of Kent Island.” You can get in touch with his story by finding your way to nearby Chester, where Kirwan’s old house in the countryside at 641 Dominion Rd. is now a little museum.

Born in 1848, Kirwan was working aboard ships as a cabin boy and a cook by the age of 10. By 16, he was the owner of the William Baynes, the first of three schooners he would captain before age 25, at which point he gave up sailing and switched over to farming and shopkeeping. 

His old general store was right here in the house, and its shelves are still full of goods from his day, most of them keepsakes that remained in family hands until they were donated to the heritage society. Kirwan’s farm covered 300 acres—it had a lumber mill, a turtle farm, a cooper’s mill, a blacksmith’s shop, and much more. He served in the state senate and as a commander in the “oyster navy,” but he remained most famous for his leadership of that march on Washington by the Kent Island Home Preservation Committee. 

Offered over $3,000,000 for Kent Island, Mr. Kirwan was among the many who felt that there was not enough money in the mint to justify moving off the native heath.

Another sweet view of that native heath awaits at Kent Narrows, named for the waterway that runs right up through the island at the western edge of Chester. On the north side of the highway there, you can walk out to Ferry Point Park, a wishbone-shaped strip of land that extends out into the Chester River, serving up glorious views. The nearby Chesapeake Heritage & Visitors Center has brochures, exhibits, and restrooms. The Cross Island Trail is accessible from here as well. 

Both sides of Kent Narrows offer an abundance of seafood options, ranging from simple outdoor tiki huts to fine-dining affairs. Kent Narrows might well have more outdoor tables than any other place on the Shore outside of the beach resorts. Be sure to check out the Maryland Watermen’s Monument on the south side of the Narrows—it stands down near the base of Watermen’s Memorial Bridge. 

Waterman's Monument on Kent Island

The Watermen’s Monument

Last but not least, wander through Grasonville on the eastern side of the Narrows to find your way to the Chesapeake Bay Environmental Center, which offers a network of trails that wander through marshland and along shorelines, providing some great birdwatching opportunities. You can rent kayaks there in the warmer months as well. 

Thank you for reading. Every chapter in my Road Trips books includes four other things
• A map giving a general orientation for where this trip sits on the Delmarva Peninsula
• A list of names, links, and addresses for tourism resources and destinations mentioned in the chapter
• A list of the other trips in each book that are within close geographic striking distance of this one
• An after-chapter interlude from days gone by. Usually called “Way Back Machine,” these sections tell stories from days gone by designed to help readers get in touch with the history and culture of a place. That Way Back Machine in is titled “The Best-Laid Plans,” and it runs the various alternative Bay crossing proposed during the decades before the construction of the Chesapeake Bay Bridge.

• This excerpt from Eastern Shore Road Trips #2: 26 MORE One-Day Adventures on Delmarva was posted by Claudia Colaprete on August 8, 2022 for Whimbrel Creations LLC/Secrets of the Eastern Shore. All rights reserved.

• Thank you so much for spending a little time with this story and on this site!

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