Maryland State Archives

By J.S. Houck

In Annapolis and Anne Arundel County, many an inn, tavern and bed-and-breakfast—in fact, almost any building with four walls built before 1799—claims to have hosted or possibly hosted our nation’s founding father, George Washington. Who’s telling the truth and who’s chopping down cherry trees?

Did George Washington really sleep here? Well, it’s indisputable that he slept somewhere in our colonial capital, and many places could have provided the bed and bedding in which our country’s first commander in chief rested his saddle-sore bum and weary politico head. Actual proof is a little harder to come by.

But for locals and tourists alike, the Washington connection provides an opportunity to walk, dine or rest in the footsteps of the great man himself. It adds a personal dimension to our experience of him, appeasing that desire to discover the little things that don’t make it to the history books.

For starters, it is well documented that Washington traveled throughout the whole of Maryland numerous times during his life, for many reasons: personal, military, political, and otherwise. Furthermore, Washington’s travels took him through Anne Arundel County and, more specifically, Annapolis. Annapolis served Washington as a rest stop between Mount Vernon and his Northern destinations (Philadelphia, Boston). But Annapolis was much more than simply a place to "juice-up" the horses, re-supply and play shut-eye. Washington had many personal interests in Annapolis and he documented them in his journal accordingly.

In August of 1751, at 19 years of age, Washington first visited and stayed in Annapolis. Having come with his brother Lawrence, Washington purportedly stayed at Daniel Wolstenholme’s, a merchant involved in the West Indian trade. Wolstenholme’s was located at the Ferry landing on the Severn River, at the foot of the road, which is the extension of Northeast Street, what is present day Maryland Avenue. Five years later, we learn by way of the Maryland Gazette and Washington’s ledger, he passed through Annapolis at least three times, having stayed at Wolstenholme’s, on his way to Philadelphia. He was then a Colonel in the Virginia Regiment during the French and Indian War

Military obligations aside, Washington enjoyed the pleasures of Annapolis, particularly horse racing. As the epicenter of Chesapeake horse racing, particularly during the early 1770s, Annapolis played host to the gentry of the time. The fall horse races drew crowds from near and far with hopes of winning the purse. During the racing seasons, dinners, balls, plays and general socializing abounded throughout the city. Washington was here to play both bettor and social butterfly. The color of such history shines throughout Washington’s meticulous journal entries:

1771 September 21

Set out with Mr. Wormely for the Annapolis Races. Dind at Mr. Willm. Digge’s and lodgd at Mr. Ignatis Digge’s.

22. Dined at Mr. Samuel Galloway’s and lodged with Mr. Boucher in Annapolis.

23. Dined with Mr. Lloyd Dulaney and spent the evening at the Coffee House.

24. Dined with the Governor [Robert Eden] and went to the play and ball afterwards.

25. Dined at Dr. Stewart’s and went to the play and ball afterwards.

26. Dined at Mr. Rideout’s and went to the play after it.

27. Dined at Mr. Carroll’s and went to the ball.

28. Dined at Mr. Boucher’s and went from thence to the play and afterwards to the Coffee House.

During this time, Washington records losing over L13, presumably during card games, as opposed to the horse races (on subsequent visits, Washington does record his loses on the races).

Of particular interest are the notes regarding Washington’s lodging. Who was Mr. Jonathan Boucher, who figures prominently early in this visit to Annapolis and during later visits? Mr. Boucher was rector of the first St. Anne’s Parish (the third of which is still standing) and housed Washington’s stepson, John Park "Jacky" Custis, during his schooling in Annapolis. Custis is known to have extended an invitation on behalf of Boucher to stay at his house, as it would be "almost impossible to get a Room at any of the ordinaries, the Rooms being preengaged to their [regular] customers." Boucher and Custis were living in the St. Anne’s Parish parsonage, located on Hanover Street.

Washington also makes mention of his stay at The Coffeehouse. The Coffeehouse was a popular tavern run by a Mrs. Howard and was located on Main Street (now Church Street) near the State House (Maryland. Gazette, September 12, 1771). On successive visits to Annapolis for the fall races, Washington dined and lodged with many of the same personages.

While the ensuing years saw Washington traveling to and from Annapolis with consistency, it was in December of 1783 when Washington made his most famous and well-documented visit to Annapolis—his resignation from the Continental Army. During this very emotional and significant stay, Washington quartered at the new Mann’s Tavern (also known as Mann’s City Hotel), located at 162 Conduit Street. Today, the property has ceded to tourism of another sort—Annapolitan souvenir shops.

Washington’s last apparent visit to the city was in March of 1791 at 59 years of age and as President of the United States. The journey from Rock Hall by ferry towards Annapolis was particularly interesting, as Washington describes in his own words:

"Unluckily, embarking on board of a borrowed Boat because She was the largest, I was in imminent danger, from the unskillfulness of the hands, and the dullness of her sailing, added to the darkness and storminess of the night…after 8 Oclock P.M. we made the mouth of the Severn River (leading up to Annapolis) but the ignorance of the People on board, with respect to the navigation of it run us aground first on Greenbury point [entrance to the Severn on the north] from whence with much exertion and difficulty we got off; & then, having no knowledge of the Channel and the night being immensely dark with heavy and variable squalls of wind-constant lightning & tremendous thunder-we soon grounded again on what is called Hornes point [present-day Eastport] where, finding all efforts in vain & not knowing where we were we remained, not knowing what might happen, ’til morning."

Washington was eventually "rescued" and lodged in Annapolis at Mann’s Tavern, making for an overall exhausting twentieth (estimated) and final trip to town.

Many generalizations have been made as to when and where Washington has dined, danced, supped and lodged during his travels to and from Annapolis. City properties, such as present-day Middleton Tavern at 2 Market Space, the Charles Carroll House at 107 Duke of Gloucester, the Hammond-Harwood House at 19 Maryland Avenue, and the Jonas Green House B&B at 124 Charles Street, all report possible ties to Washington. There is no doubt that Washington employed the services of local merchants, friends and dignitaries while staying in Annapolis and while traveling through Anne Arundel County. And while many locales claim a connection, the ultimate truth lies within the context of Washington’s personal writings and somewhere between 5 and 7 feet, below ground, in a grassy plain, at the foothills of Mount Vernon.

Special Thanks extended to Susan Steckman, Heather Ersts Venters and Greg Stiverson at the Historic Annapolis Foundation.