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The Land of Pleasant Living

Donna and I took our first of hopefully many post-retirement trips right before the Independence Day weekend. Our destination was one of my favorite places, Maryland’s Eastern Shore. I went to college at Washington College (the Shoremen), in Chestertown, in the northern portion. It was my first real exposure to the region, and I fell in love with the slow pace, rural landscape, small, ancient (by U.S. standards) towns, and ubiquity of water. In many ways, it is similar to another of my favorite places – Ireland.

The Eastern Shore is bounded by the Chesapeake Bay to the west and the Atlantic Ocean to the east. The wide rivers, creeks and inlets dominate the land. In the North, the Chester River, Wye River and Miles River all flow to the Bay between St. Michaels and Kent Island. To the south, the Choptank River, Island Creek, Tred Avon River, Broad Creek and Harris Creek enter the Bay from the north and south of Tilghman Island.

For centuries the water and the life it supports has been foundational to the economy. Harvesting blue crabs, oysters, rockfish, bluefish, and other seafood has been the work of many generations of watermen. The land, on the other hand, produces mostly corn and soy beans.

To get to the Eastern Shore from Baltimore or Washington, D.C., you head east past Annapolis to the 4.5-mile-long Chesapeake Bay Bridge, which takes you from the Western Shore to Kent Island, a four-mile-wide island that Trip Advisor says was the location of the first European settlement in what is now Maryland. You drive through Kent Island and cross the Kent Narrows Bridge, which puts you onto the Eastern Shore.

My wife and I disagree on this last point. She contends that Kent Island is part of the Eastern Shore, which raises a deep philosophical question: What constitutes the Eastern Shore?

We do agree on a critical point: That the Eastern Shore is defined by a feeling at least as much as by geography. Its unofficial motto (coined in the 1950s by the brewers of local National Bohemian beer) is The Land of Pleasant Living. Donna points to the beautiful parts of Kent Island off the main highway as just as serene and peaceful as the best of parts east, and, as it is separated from the Western Shore by the Chesapeake Bay, is therefore part of the Eastern Shore. 

My position is that regardless of the parts of Kent Island that pass the Pleasant Living test, the highway that carries travelers from one shore to the other is a corridor lined by big-box stores, strip malls, and fast-food dispensaries. Driving is harried and frantic. Until you cross the Kent Narrows bridge, you can’t exhale and you can’t loosen your stranglehold on the steering wheel. But once you cross the narrows and leave Kent Island, you have truly achieved a state of Pleasant Living. In other words, you have arrived on the Eastern Shore.

Chestertown

Once we put the Western Shore behind us, we took Route 213 north to Chestertown on the Chester River. We were both hungry, so we stopped at a restaurant we knew right on the water. To our chagrin, we found out a kitchen fire in January had closed the restaurant, but a food truck in the back was offering a few items and they had cold beer. We ate on a patio under a large tent, looking out on the river and admiring the occasional boat motoring or sailing past and the several in the marina adjacent to us.


After lunch we strolled around the town of about 5,000. Europeans settled on the Eastern Shore in the 1600s and many riverside towns became important ports before larger ports, in Baltimore and Philadelphia, overtook them in importance. Coupled with the fact that the Eastern Shore has not been impacted greatly by development, the result is that many structures from Revolutionary times and before remain.

Chestertown served as an important port in the 1700s and 1800s, and many of the stately brick homes on Water Street and High Street were built around the time of the Revolution. Side note: There was a tax revolt in Chestertown that pre-dated the Boston Tea Party, complete with townspeople boarding a docked ship and tossing into the river barrels of tea imported from England. The Chestertown Tea Party is re-enacted each summer; here’s a link with more information.

After our stroll we got in the car and drove a mile or so to the college so I could reminisce. It’s a beautiful campus and like most things in Chestertown, it is old – the 10th oldest college in the nation (founded in 1782 and funded in part by a large donation from George himself. He also served on the board of governors for six years.) More photos of Chestertown and Washington College are below.

Easton

Saying good-bye to Chestertown, we drove an hour south to Easton and checked into our hotel. Easton, the seat of Talbot County and an old city in its own right, was settled in the 1600s. In 1710, Maryland’s Assembly voted to erect a courthouse in the village. Today Easton has a population of 16,000 and like Chestertown is adorned with beautiful old homes and buildings. The town is a popular destination for tourists and waterfowl hunters and supports many good restaurants and galleries, a lively arts scene, the annual Waterfowl Festival, music festivals, and other happenings.

The next morning Donna wanted to have breakfast at a place she had found online called Breakfast in Easton. We put it into our GPS, which said it was 800 feet away from us. We walked the prescribed route and when the GPS announced that we had arrived, the restaurant was nowhere to be found. There were two old buildings separated by a narrow, winding brick walkway that didn’t seem to lead anywhere. Behind the buildings was a gravel parking lot for the nearby courthouse. 

We walked around the buildings and found, on the other side of a fence, a couple groups of people sitting around picnic tables; all we had to do was to figure out how to get there. We went back to the brick path, which was overgrown with trees beside it, until we came to a side door, where a bearded man in an apron was bringing in supplies. He told us to keep walking, and we found our way to the hideaway eatery tucked into a beautiful lush garden. 

A hippie-ish girl at a counter inside told us to pick a table inside or out and to help ourselves to coffee and water, which were on a table outside. We did, then she came and took our orders. It was one of those unexpected little adventures that make traveling so rewarding.

St. Michael’s

After breakfast we drove to St. Michael’s, a largely tourist destination where the Wye and Miles rivers join. We visited the fascinating Chesapeake Bay Maritime Museum, a campus with a lighthouse you can walk up and through; a working boatyard; historic boats and painstakingly built replicas of old boats; and traditional museums. 

There was a vessel that looked like an 18th century tall ship with workers scurrying around on it. I asked one guy what it was, and we ended up talking for 20 minutes. He must have been the project manager. 

The boat had been in construction for three years and was modeled on a ship from the 1700s called the Dove. With a displacement of 40 tons, the Dove was a close-to-shore escort to ocean-crossing cargo ships 10 times larger. The project manager told me everything on the new Dove had been made on the museum’s campus, except for the sails, which were made by a sailmaker in Maine. Construction of the Dove had been contracted by a not-for-profit educational entity in St. Mary’s City on Maryland’s Western Shore.

Another interesting aspect of the museum was an exhibit exploring the tensions over the years between those who make their living on the water and those who use the Bay for recreation. It’s like so much of our nation’s past – the conflicts between those who occupy territory and those who come later to push them out.

After the Maritime Museum we found a sightseeing boat offering tours of the Miles River. We hopped on for the 90-minute cruise. The captain provided more history of the river and the town and context about the owners of the spectacular estates that line the wide Miles and pointed out where key scenes from the movie Wedding Crashers were shot. More photos from that cruise are below.

Bellevue and Oxford

We headed back to the car and took a pretty lane through farmland to our next destination, Bellevue, on the Tred Avon River. The town consists of tiny, old, well-kept homes that likely have housed watermen for generations. The village made us think we were in a time warp. 

At the end of the lane was a marina with a half-dozen work boats, a small beach where a family was trying to beat the oppressive heat by splashing in the water, and the Oxford-Bellevue Ferry, which has been operating at that site for 339 years. Since 1683, nearly 100 years before the American Revolution, the ferry has operated continuously. A plaque on the ferry estimates there have been some 800,000 crossings totaling 1.2 million miles, equaling 48 times around the earth or five trips to the moon.

The ferry crosses the river every 10 minutes. When it arrived at the Bellevue dock and disgorged its passengers – four cars and a few bicyclists and walk-ons – we pulled our car onto the boat, got out, and enjoyed a beautiful, breezy trip across the calm Tred Avon to Oxford, still another pre-Revolutionary town with gorgeous homes along the river and throughout the tiny burg (population 611).

We strolled to the Robert Morris Inn, which bills itself as the oldest inn and tavern in America and has been in operation since 1710. The inn, originally called Riverview House, was a home of Founding Father Robert Morris. Morris gained fame as the “financier of the Revolution” and the wealthiest and most powerful man of his time. Along with Alexander Hamilton and Albert Gallatin, he is regarded as one of the founders of the financial system of the United States. He served as a member of the Pennsylvania legislature, the Second Continental Congress, and the Senate and signed the Declaration of Independence, Articles of Federation, and U.S. Constitution. You can read more about his life here.

After a cool drink in the inn’s tavern, we drove another 15 minutes back to Easton. After another great dinner in another fine restaurant, we returned to our hotel and relaxed at a table on the enormous porch for a while before retiring for the night. The next morning, after breakfast in the hotel’s restaurant, we packed up and returned to our home on the Western Shore. It was a wonderful way to look back on our country’s origins as we celebrate its 246th birthday, and a wonderful way to celebrate my retirement.

More Photos

 

Boatyard, Chesapeake Bay Maritime Museum

Washington College Student Services Building

Washington College Dunning Hall

Washington College

Washington College William Smith Hall

George


St. Michael's


On the Miles River

On the Tred Avon River

The Inn at Perry Cabin, on the Miles River

St. Michael's

On the Miles River

On the Miles River

On the Miles River

On the Tred Avon River

On the Tred Avon River

The Oxford-Bellevue Ferry

The Dove

The Dove

Boot scrapes, Chestertown

Chestertown

Chestertown

Chestertown

Chestertown

Work boat, Bellevue

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