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Retracing George Washington's Travels

By Anne McNulty

As one strolls along the tree-lined streets of those two grande-dame towns of Annapolis and Chestertown, one can almost hear the sounds of long-ago days echoing on the crooked, brick sidewalks. Imagine the clatter of carriage wheels and the steady patter of horses’ hooves, trotting on cobblestone streets and passing by elegant brick homes and humble frame cottages. Imagine a young man astride one of these horses. He sits upright in his saddle as he rides through these towns. This young officer of the Virginia Regiment is a man with a purpose. He is traveling the road to success and he is traveling through Annapolis and Chestertown to get there. His name is George Washington.

 

 

Washington didn’t have an easy road to travel.In fact, he used only two routes when riding from Virginia to Boston. The first, the Western Overland Route, was the equivalent of a colonial I-95.“ This route was lined with taverns, which were the Motel 6’s of the day,” says Adam Goodheart, Director of the C.V. Starr Center For the Study of the American Experience, located in Chestertown. When Washington traveled this route, he would ride north from Virginia; through Prince George’s and Anne Arundel Counties; up through Baltimore; then east to New Castle, Delaware to points north.

His shorter route consisted of boarding a ferry-boat after reaching Annapolis. The small vessel, usually lacking a cabin or below-deck, would sail him across the Bay to Rock Hall. After making that crossing, he could again mount his horse or rent one and ride north to Chestertown, a three-hour trip; then on to Philadelphia, New York or Boston. On at least one trip, he also ferried across the Christiana and Schuylkill Rivers.

The six-foot-four Washington had no difficulty with horsemanship. He was an avid rider who rode about 15 miles every day for exercise. Yet even Washington, after jostling on his horse for hours in a whipping wind or riding in soaking rain, surely welcomed sitting next to a tavern’s blazing fireplace and downing a stiff drink.

“These early taverns were rated not so much for their accommodations as for the quality of drinks they served,” says Goodheart.





One establishment Washington visited, was Daugherty’s Tavern located on High Street in Chestertown. Its proprietor, Mr. Daugherty, was a great story-teller and jokester, and he often shared a glass of his excellent lemon punch with George.Washington also drank a glass or two at Worrell’s Tavern on Cannon Street during some of his seven visits to Chestertown.

An incredibly meticulous record keeper, he duly recorded every place he stayed and every expense he incurred. “He kept the receipt for every bill he paid, and filed it away. You can see where he had breakfast in 1771.”says Goodheart. “Today, it would be like keeping every credit card receipt.”

 

THE ROAD TO AMBITION

In 1756, young Colonel Washington was fighting raiding Native-Americans on the Virginia frontier, but he was an unhappy man. He was chagrined that as a colonial officer, he would always have lower rank than a British officer. He could only achieve the promotions for which he longed if awarded a royal commission in the British army.

Since his letters to British Governor Shirley in Boston, requesting a commission produced no effect, he made the 1000 mile trek to Boston to present his case in person. He left Virginia in February 1756, but upon his arrival, Governor Shirley could not award him his commission. Dejected, Washington left Boston and according to the Maryland Gazette, spent the night of March 22nd in Annapolis before returning home.

A year later in 1757, Washington again tried to obtain a royal commission—this time from Virginia governor, Lord Loudon, who was attending the Southern Governors’ Conference in Philadelphia.Washington left his military post and traveled the snowy roads from Alexandria to Philadelphia.He arrived in Annapolis on February 15th, ferried to Rock Hall, stopped at Chestertown and rode up to Pennsylvania.After pleading his case,Loudoun haughtily dismissed young George and denied his request.Bitter and disappointed, the lanky red-head left Philadelphia on March 23 and was in Annapolis on the 30th.






The first of his estimated 20 visits to the town had occurred in August 1751 when he was 19 years old.He and his brother Lawrence, reportedly stayed at the home of merchant Daniel Wolstenholme who lived on what is now Maryland Avenue.But that was a social occasion.This time, the crestfallen soldier wanted to return to Virginia as quickly as possible.

 

 

THE ROAD TO SUCCESS

After capturing Fort Duquesne in 1758 during the French and Indian War, Washington felt stuck in an unrewarding military career. He’d had enough.Now he was ready to embark on another way to success by entering politics and building up his wealth, which already included about 2000 acres.In 1759 he won a seat in the Virginia House of Burgesses, and also won the hand of a plump, little widow named Martha Custis.After his brother Lawrence passed away, Washington inherited Mount Vernon in 1771.

It was also in 1771 that he traveled to Annapolis mainly to hobnob with the elite of Annapolis society.This included betting on horse races, playing cards, and attending parties and balls.During his stay, he spent the night of September 22, at the home of his friend, Reverend Jonathan Boucher, rector of the first St. Anne’s Parish and tutor to Washington’s stepson, John Parke Custis (Jacky).He subsequently dined with Governor Eden and also with the Carrolls’, Stewarts’ and Rideouts’.Later in the week he dropped in at the Coffee House.

In 1773, the successful land-owner faced a most challenging task-- enrolling Jacky in a proper college.Like all anxious parents, he wanted the best school for Jacky, who was an indifferent student at best.Washington’s list did not include the College of William and Mary in Virginia.He was dead-set against enrolling him in that ‘party school.’

In a letter written to Rev. Boucher, he wrote,“I cannot think William &Mary College a desirable place to send Jack to.The inattention of the masters, added to the number of hollidays is the subject of general complaint & affords no pleasing prospect for a youth who has a good deal to attain.”

Boucher wrote back advising him to try Kings College in New York—now Columbia University. Boucher maintained “That it was the most fashionable and polite place on the continent and favorably compared to Oxford and Cambridge.”





So Kings College it would be and in on May 10th Washington set off to take Jacky to school.

They arrived in Annapolis on the 11th and stayed with Governor Eden for two
nights. The next day all three took the ferry to Rock Hall and subsequently rode to Chestertown. Here they dined with Governor Eden’s brother, Captain Thomas Eden on his ship The Annapolis. That evening, Washington and his entourage went to the Hynson-Ringgold House on Water Street, a street lined with imposing homes belonging to the rich merchants of that day. His diary notes,“Supped and lodged at Mr. Ringolds.”

 

REVOLUTION

Washington passed through Annapolis and Kent Counties again in September of 1774 when he was elected by the Virginia Convention to attend the First Continental Congress in Philadelphia, held after the infamous Boston tea party. He and his fellow travelers Patrick Henry and Edmund Pendleton, were in a rush and made the trek from Mt. Vernon to Annapolis in one day. They stopped there to eat and then ferried to Rock Hall, but the harried men couldn’t travel any farther because they were still waiting for Washington’s horses to arrive. Finally, perched in saddles, they rode to Chestertown where they spent the night. They left without eating breakfast.





At the congress, fiery Patrick Henry galvanized the delegates with his dazzling speech.“Give me liberty or give me death,” he shouted in conclusion, as he raised an imaginary dagger to his chest and sank into his chair.

Six weeks later, the Congress was dismissed and Washington rushed to get home. He lodged at Chestertown on October 28th, rode to Rock Hall first thing in the morning of the 29th and ferried to Annapolis that afternoon. He was home by the 30th.

When the second Continental Congress was convened in May 1775, Washington was appointed Commander in Chief of the Continental Army. On July 3, 1775 he took command of his poorly trained troops and embarked on a grueling six-year war that would change the world.

 

In 1782 after the war was won, Washington, now perceived as a man of fame and stature, received a letter from Dr. William Smith the head of the Kent County Free School. The school had been renamed Washington College as a tribute to him.In response Washington donated 50 guineas.Washington wrote,“It’s only a trifling sum.” He also apologized that he could not sit on the college board or travel to Chestertown because of his busy schedule.He did visit the college in a later trip made in May 1784, where he lodged at Worrell’s Tavern.

 

Perhaps Washington’s most important trip was the one he made to Annapolis in 1783 to resign his commission in the Continental Army. By now he was the most famous man on the continent and many expected him to become king. But Washington would have none of it.
 On Friday, December 19th, both he and Martha and arrived in Annapolis to a large welcoming committee and a 13 gun salute.After being profusely greeted, the Washingtons’ headed to Conduit Street down to Mann’s Tavern, where they would lodge. The whole town feasted over the weekend, and on Monday over 200 carriages jammed the narrow streets to attend a dress ball at the new brick State House.

On Tuesday noon, Washington’s carriage rolled up the hill from Conduit Street to the packed State House where he would give his resignation speech.

His hand shook and he choked back tears as he read his short speech.To the weeping assemblage he said,“I here offer my commission and take my leave of all the employments of public office.”

Once again, he would return to his beloved Mt. Vernon.But president he would become in 1789, and now the whole world was watching this self-made man and his bold experiment in Democracy.

 

THE SOUTHERN TOUR

The most adventurous journey the president took was in 1791 when he was 59 years old.Although he would be appalled by all the pomp and circumstance surrounding the president today, he did display some pomp of his own when he embarked on a presidential tour of the Southern states in late spring.His coach-of-state pulled by six, white horses covered 1900 miles in 10 weeks.

On March 23, he reached Chestertown, dined and lodged at Worrell’s Tavern. He and his extensive entourage, left at 6:00 am on the 24th and rode to Rock Hall.Upon his arrival, the president discovered that there weren’t enough boats to carry his chariot, horses, servants, and baggage. Temper mounting, he waited impatiently until 3:00 pm when he took the largest ferry and started across.It was a calm evening, but at sunset the Chesapeake whipped up a furious gale.

Washington writes,“The crew having no knowledge of the channel, made things worse.”Soon they grounded the boat at Horne’s point. (Eastport)

The President of the United States spent the night huddled up in his great coat and shivering in his boots. Exhausted, he jammed himself into a cramped berth.

The next morning, another boat sailed by and rescued the Commander-in-Chief. The Maryland Gazette deciding this might make a good story, wrote about the “Chief Treasure of Maryland and his Chesapeake adventure.”

It would be the last Chesapeake adventure for the tired Washington. After his eight-year term was completed, he retired to Mt. Vernon where he contentedly remained until his death in 1799. His travels were over.

Many thanks to historian Benjamin Kohl-Vice President of the Kent County Historical Society, Adam Goodheart, John R. Bohrer, author of George Washington in Kent County Or, the Curse of the Rock Hall Ferry. Other source—George Washington—A Life—by William Sterne Randall.

George Washington

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