Chesapeake Retreat on Maryland’s Eastern Shore

An intricate web of gleaming steel girders supports the bridge that spans Chesapeake Bay between Annapolis and Kent Island. Our rental car races through a gauntlet of flashing gridwork suspended on taut cables above blue waters. Like tourists of yesteryear, we are headed for Maryland’s Eastern Shore and anticipate a feast of crab cakes, oysters and beaten biscuits upon our arrival in St. Michaels.

When the Industrial Revolution took hold in the cities on the mainland, city dwellers started eyeing the Eastern Shore for relief from soot, smoke and brick factories; density, noise and a hectic pace of life. By the 1870s, they wanted to escape. Resorts started cropping up on the Chesapeake peninsula, most notably Ocean City on the Atlantic side. Steamboat and rail companies began devising plans to get potential tourists there faster.

A few miles outside of St. Michaels in Talbot County, three enterprising locals worked with the Baltimore and Eastern Railroad to build a steam and ferry dock at New Claiborne and a spur line running to the central town, Easton. From there, excursionists could board a train for Ocean City. The beauty of the Eastern Shore landscape, however, stopped many of them in their tracks. Forget the crowded revelry of Ocean City; here was bucolic paradise!

“It was the simple country life and the lure of the water that attracted city people. In those days, they brought steamer trunks and stayed for the summer,” writes Margaret Barton Driggs in her article on Claiborne. Throughout Talbot County, farms started taking in boarders, and camps and inns rose to meet the demand for pastoral retreat.

Wades Point

We cruise past green fields dotted with white colonial houses bordered by forests of hardwood trees just breaking into leaf. Here and there the white flowers of dogwood trees punctuate the fresh green of spring. Wisteria vines reach high into the trees, their purple clusters transforming the leafy landscape. Crabapple and crape myrtle have exploded into exuberant white and pink blossoms. Small bridges span hundreds of inlets whose reeds are still brown and stiff with winter. Swans float lazily in rush-lined ponds, and we make the final turn for the Feiler family’s Wades Point Inn, our home for the next four nights.

Steeped in history, the Georgian main house, fronted by double-decked front porches, was built in 1819 by Thomas Kemp, a well-known and prolific ship builder in Baltimore. Born on the Eastern Shore, Kemp returned to purchase the 236 acres of Wades Point and Hatton in 1813, four months after the British attack on St. Michaels during the War of 1812. The Brits had landed barges at Wades Point and shot up the old main house built by John Leeds, a famous mathematician and astronomer.

Leeds’s house was threatened by the erosion caused by the storms and tides that carve the ever-changing landscape of the Eastern Shore, so Kemp built a new home. (Of the original 900 acres of Wades Point and Hatton, only 236 remained for Kemp and only 120 remain today.) Kemp burned a forest of pine trees to fuel the brick kiln that he kept burning day and night. Eventually, the bay claimed the remains of his old house, and for years its foundations could be seen in the shallow waters offshore.

At Wades Point, the master ship builder became a farmer. His farm grew flax, rye, wheat and corn and sold sheep’s wool, feathers, potatoes, apple brandy and cider. Thomas Kemp died in 1824. His remains lie in the family plot on the highest knoll of the property alongside his many descendents. Today, oaks and tall grasses shelter the tiny graveyard overlooking the farm.

In the latter part of the 1800s, the Kemps started taking in boarders and charging them, and John W. Kemp added a Victorian wing in 1890. In 1920, Mildred Tunis Kemp took over the running of Wades Point’s boarding house. By then, the farm, like Maple Hall in Claiborne and so many other bay and riverside inns, had honed its skills at entertaining guests. Wades Point had a casino for dancing and a clubhouse called “The Roost.” Everywhere, Talbot County visitors could find swings on porches for lazy afternoons, oyster frys by the water, and swimming and boating on hot summer days. Other activities included fishing, crabbing, golf, tennis, camping, hunting and baseball.

Promoting Tourism

Helping to promote tourism in Talbot County were the various rail and ferry companies that published brochures touting the recreational and historic features of the area, such as the 1710 Robert Morris House in Oxford which became an inn. (Morris Junior helped finance the American Revolution and signed the Declaration of Independence, the Articles of Confederation and the Constitution of the United States.)

Tourists that we are, we rent bicycles and take the winding country road to Bellevue where the oldest still-operating ferry in the United States will shuttle us to Oxford. We raise the yellow signal and wait for the nine-car ferry to chug across the Tred Avon River.

Commissioned for “horses and men” in 1683, the ferry moved traffic and goods through Oxford, one of two ports of entry during Colonial times. Originally, the ferry was a scow (a flat-bottomed, broad-bowed boat) propelled by sculling (moving a long oar at the stern from side to side). In 1886, sculling was replaced by a steam tug that towed the scow across the river. In 1931, the first self-propelled ferry made its appearance.

The “lure of water” is the Eastern Shore’s greatest draw, and the Chesapeake Bay Maritime Museum in St. Michaels explains it all through stunning interactive exhibits of shipbuilding, oyster dredging and tonging, lighthouses, recreation and Chesapeake life. St. Michael’s is famous for being the town that fooled the British during the war of 1812. Legend has it that the citizens placed lanterns in the trees behind the town so that British cannons would overshoot the village. Its colonial roots are evident along the downtown streets and in its many small harbors.

The oysters have dwindled severely over the past few decades, as has the skipjack fleet. These oyster boats were specially designed for the shallow waters of the Chesapeake. We took a sunset cruise on one of these historic boats. Under full sail we set out upon the Miles River and learned the lore of Chesapeake sailors while we dredged for oysters. Our captain told tales of the glory days when the haul of oysters threatened to sink the boat by 10 am in the morning. Now, finding viable beds has become a rarity.

St. Michaels has been hosting an annual regatta, which includes log canoe races, since 1833. These sailboats are constructed by strapping three to five logs together and hollowing them out to form the hull of the boat. The finished product looks nothing like our image of a log canoe, but rather like a small, shallow-bottomed sailboat.


Our four idyllic days are over. We’ve played golf at Hog Neck Golf Course in Easton, paddled kayaks in the bay between Wades Point and Claiborne, hiked along ponds and corn fields and orchards, gloried in magnificent sunsets over the bay and eaten our fill of crab cakes, oysters and scallops. We roll ourselves and our suitcases to our waiting car and think of other departures.

One hundred and forty years ago, steamer trunks were conveyed by hackneys to steamboat landing. After the ferry and rail system was built, excursionists would arrive in gleaming white clothes from Baltimore. Judge Tolson Cockey, whose family owned Maple Hall at Claiborne, recalled that on Sundays they would return in a smudged and bedraggled state. “We called the train – it was the BC&A – the Black Cinders and Ashes,” he said in explanation. In the 1910s and ’20s, the ferries began catering to automotive traffic and Sunday evening traffic was backed up for several miles waiting for the return trip.

In 1952, the Chesapeake Bay Bridge, the longest bridge in the world at the time, was built. The ferry stopped running and the town of Claiborne grew quiet. The tourists didn’t stop coming to the Eastern Shore, however. In 1973, a second, parallel bridge was built to alleviate congestion on the original two-lane span.

Now as then, city dwellers long for “the simple country life” and the allure of water.

(Special thanks to Beth Hanson, curator of the Talbot County Historical Society, for her generous assistance. Sources: “Thomas Kemp, Shipbuilder, and His Home, Wades Point,” by M. Florence Bourne; “The Last Hotel” by Harold D. Jopp, Jr.; “Claiborne” by Margaret Barton Driggs; various contemporary and historical brochures.”)