Middleton Tavern

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This long favored watering hole still has spirited, fun-loving spectral clientele!

A politically incorrect spirit expects certain standards to be maintained.




Middleton Tavern is in a 1740 Georgian building which originally was a private residence. The Georgian style of architecture was named in honor of the “four British kings named George, who reigned from 1714 to 1830.” It is a 3 story, solidly built brick structure which has a “simple, balanced appearance,” giving an impression of “order and stability,” being true to the Georgian style building. It operates as a restaurant and bar on the first floor and has an awning-covered outside eating area, with tables which face the sidewalk, great for people watching!

Going through the thick wooden doors, one finds the four dining rooms and interesting items from its very long history on the wall. The piano bar is in the back of the restaurant, with a side entrance. This highly rated restaurant specializes in great sea food as it is in a sea port town.

Entertainment is also offered in the Piano Bar, and special meals are offered on holidays like thanksgiving, if you make reservations before hand.




In 1750, the owner of this 1740 private residence, Elizabeth Bennett, sold her home to Horatio Middleton, a ferry operator who by law needed to have lodging for his customers. His ferry ran round trip from Annapolis to Rock Hall, which cut the travel time from Philadelphia to Virginia immensely. Horatio then turned this residence into the Middleton Tavern, which also became a very popular place for the townspeople to congregate and socialize as well. Lovely gardens stretched from the edge of the water to Prince George Street. Yes indeed, Middleton Tavern was a classy place, where not only the Maryland Jockey Club and Free Masons held their meetings, but the Tuesday Club, made up of “enlightened, well-educated gentlemen” also met there for years.

After Horatio died, his wife and then his son, Samuel continued to run both the ferry business and the tavern as well.

During the Revolutionary War era, George Washington, Thomas Jefferson and Benjamin Franklin stayed here during their travels. Other members of the Continental Congress also stayed in this tavern on various occasions when they met in the Maryland state house.

Throughout the years, this solid building held a lot of businesses. During the late 1800s it was home to a general store and meat market. In the early 1900s, it became Tydings’ Bar. The Mandris Family bought the building and set up a restaurant /soda counter and a souvenir shop. In 1968, Jerry Hardesy bought the building and gave the establishment it’s original name, the Middleton Tavern.




It is hard to say exactly who is still hanging around this building, as so many people have been connected to this place through its 266 years of existence. There are clues to the period from which one entity comes from, though for other entities it is still a mystery from what era they came from.



An unknown entity who haunts the first floor dining rooms, is called Roland by the staff.

This entity has appeared, dressed in revolutionary era clothing, looking intently out one of the dining rooms’ window which has a view of the water, where the ferries used to dock, as if he is waiting for the ferry to come in.

This entity is the active spirit who announces his presence by the aroma of cigar smoke, though no smoking is allowed for the living; apparently just for entities who aren’t politically correct!

This entity tosses plates and glasses one at a time off shelves, and also gets chuckles by knocking over tables full of dirty plates.

Other unknown entities may also be residing in this tavern.

Unexplained shadowy figures have been seen moving across the dining rooms.

They get their chuckles by turning the lanterns mounted on the walls throughout the restaurant upside down, to get a little attention from the living.

Tables and chairs are often moved around without any help from the living.


Yes indeed! While no one knows for sure who is haunting the tavern, Ronald could be a past owner of this building, who has issues with dirty dishes sitting around (Bullock Hotel) or perhaps doesn’t approve of the type of plates & glasses used, or resents the living using his building as a restaurant (Catfish Restaurant).

Possible identity of other shadows – Turning the lamps upside down and moving tables and chairs sounds like the jokesters could be past members of the Tuesday Club, perhaps still enjoying their memories of the many meetings they had in this building. The Tuesday Club was made up of “young enlightened and well educated gentlemen” who were a spirited lot, known to “entertain themselves with song, dance, frequent toasts and copious amounts of good cheer.”




2 Market Space
Annapolis, Maryland

Middleton Tavern can be found in the historic down town section of Annapolis, located on the corner of Dock Street and Market Space, just before Dock Street turns into Pinkney. That’s right, many streets in this area turn into something else, meaning that you need a detailed map of down town to find this Tavern.

Tom and I found it by dumb luck. It has a huge sign across the whole side of the building which faces Market Space, which helped immensely.


  • “Middleton Tavern Through the Years”
  • Middleton Tavern Brochure – “The History of Middleton Tavern”
  • hauntedtravels.com
  • middletontavern.com
  • bbs.keyhole.com
  • almanack.prwp.com
  • hauntedtravels.com

Our Haunted Paranormal Stories are Written by Julie Carr

Haunts in Maryland