Ghostly Patriots of the Middleton Tavern

Posted: 12.09.2024 | Updated: 12.09.2024

When taking an Annapolis ghost tour, the Middleton Tavern is an essential destination. Located by the Annapolis waterfront, this sturdy establishment’s red brick exterior evokes an aura of timelessness and permanence. Inside, however, it harbors an array of unearthly activity.

Established over 250 years ago, the Middleton Tavern remains the oldest bar in Maryland. It possesses a captivating and rich past, having been said to have been visited by everyone from Benjamin Franklin to President James Monroe. Throughout its abundant history, the building functioned as the meeting site for the Free Masons and the distinguished Tuesday Club, an elite gentlemen’s society. 

Today, the site is a perfect venue to cozy up next to one of the restaurant’s multiple fireplaces, imbibe a warming beverage, and listen to a chilling ghost story. Are you eager to hear more? Discover the numerous haunting tales that crisscross Annapolis on a haunted history walk with Annapolis Ghosts. 

Who Haunts the Middleton Tavern? 

If you ask the staff of the Middleton Tavern who haunts this historic public house, they’ll most likely tell you it is the ghost of a man named Roland. According to the tavern’s corporate secretary, Christina Nokes, Roland has enacted his capers in the building’s upstairs kitchen for years. This irksome spirit spills coffee, moves silverware, switches on faucets, and tampers with the lights, making more than a few staff members nervous to linger upstairs alone. 

Once an Inn For Seafarers and Travelers

When looking for historic bars and watering holes in Annapolis, the Middleton Tavern is a surefire stop to be made. 

The Middleton Tavern was established by Horatio Middleton in 1750, purchasing the property from a woman named Elizabeth Bennett. This historic tavern stands just a few decades shy of being three centuries old. It was as an inn for sailors and a base for a ferry spanning across Chesapeake Bay.

After Horatio died, his widow Anne adopted the endeavor, later passing it on to their son, Samuel Middleton. Given its location, the tavern acted as a central depot for travelers crossing the Bay by ferry. George Washington, Thomas Jefferson, and Tench Tilghman each traveled this route, delivering important news, among other actions. 

Records indicate that during the Revolutionary War, George Mann ran the tavern. However, by the end of the fray, the tavern fell back into the Middletons’ hands, being operated by Samuel’s son Gilbert. Gilbert ran the business until sometime in the 1780s. Then, ownership passed again to the hands of a logistics officer named John Randall.

Records seem to trail off at this point — but this much is known now: the current owner, Jerry Hardesty, acquired the operation in 1968, purchasing it from Mary and Cleo Apostol. For the past 35 years, the former owners ran the establishment under the title of the Mandris Restaurant. 

Hardesty changed the name back to Middleton Tavern. Soon after, the exterior and interior of the building were restorted to their former charm. The building was enlarged and renovated again in 1983, adding an upstairs dining room to entertain private events and parties. 

The Noisy Specters of Middleton Tavern

Knowing the age of this historic watering hole, the multiple ghosts that haunt the various rooms are not astonishing at all. In fact, it might be strange if a building of such an age didn’t have ghosts.

According to staff members’ accounts, a male entity reportedly haunts the dining rooms. He has been seen clad in revolutionary-era dress, gazing out a window. This particular window displays a view of the water—the site where the ferries once docked. Might this mysterious entity be awaiting a ride on one, perhaps hoping for safe passage to the other side?

The staff call this resident spirit Roland. The smell of cigar smoke seems to accompany the specter, alerting others to his presence. He has also been known to topple plates and glasses from shelves. 

Roland is most likely to be seen in the early hours of the morning, according to the owner. For this reason, most staff remain wary of entering the tavern in the wee morning hours. 

Still, Roland might not be the only ghost that haunts this watering hole. Others have observed shadowy figures moving across the dining room. Lanterns mounted to the tavern walls have been discovered to be turned upside down, and tables and chairs have been rearranged themselves. When asked, no staff members claim to have adjusted anything. 

While Roland might simply be a cranky ghost, likely annoyed by early morning activities disturbing his peace, these other happenings appear more playful. Some have surmised they might be the antics of the former members of the Tuesday Club, a group of young, enlightened gentlemen who held regular meetings in the tavern.

Who is the Smoking Man?

For years, staff of the Middleton Tavern have divulged stories about the ghost who frequents the top-floor bar. Here, it is not a rare occurrence for unsuspecting employees to come darting down the stairs to declare an unusual experience up above. 

Night Manager Mike Conroy has seen an apparition walking across the room before him. He attests the ghost has menaced wedding parties and caused staff members to quit out of fear.

Many have reported the smell of cigar smoke when no source could be located. In addition to glassware falling off shelves and wine bottles tipping over, one unlucky employee even experienced a hand touching her own while mixing up a drink, which was then forcefully spilled.

Electronics also seem affected by this space. The first electronic cash register the tavern obtained refused to work. One might think that it may have simply been a defective model — but given the surrounding occurrences, prankster ghosts seem to be a more likely explanation. 

Just who might this aggressively clumsy spirit be? That appears to be up for debate. When Hardesty conducted a seance in the 1990s, the medium he employed mentioned a name, Roland Johnson, describing a dapper man of middle age with a penchant for smoking cigars.

Yet another Annapolis resident contests this. Tour guide Melissa Huston guesses the ghost’s identity to be a different man: George Schmidt, a man killed in front of the building in 1876. Schmidt, the owner of the building, was accosted by a bullet, shot by a drunk customer who found himself in a passionate disagreement about the local election. 

Could George instead be the one responsible for the tavern’s eerie occurrences? Quite possibly. The identity of the ghost at the Middleton Tavern may never be known, but his antics are far from subtle. 

Haunted Annapolis

Whether the ghost that haunts this storied drinking hole by a previous owner, a revolutionary-war era ferry passenger, or simply a devout former bar patron who never left remains a puzzle, the staff of this establishment has yet to solve. Given the tavern’s age, all three could be simultaneously possible.

Next time you embark on a historic Annapolis pub crawl, be sure to stop by the Middleton Tavern at 2 Market Space. Drop in to sample the fresh oysters, sumptuous crab cakes, and a variety of classic cocktails in this historic bar and restaurant. As long as you don’t overstay your welcome, the ghosts will likely leave you in peace. 

Thirsty for more ghost stories? Head over to our blog to hear more tales of haunted history and ghostly encounters, or follow us on Instagram, TikTok, or Facebook. Are you intrigued enough to take a walking ghost tour? Book one of our Annapolis ghost tours and voyage into the unknown on a spine-tingling tour with Annapolis Ghosts. 

Sources:

https://www.onlyinyourstate.com/food/maryland/oldest-bar-md

https://www.beveragejournalinc.com/new/easyblog/entry/middleton-tavern

https://savingplaces.org/stories/historic-bars-middleton-tavern-in-annapolis-maryland

https://middletontavern.com/annapolis-downtown-middleton-tavern-about

https://whatsupmag.com/food-and-dining/reviews/restaurant-review-cherries-jubilee-spirits-middleton-tavern

https://www.cbsnews.com/baltimore/news/wheres-marty-discussing-who-the-ghost-of-middleton-tavern-might-be

https://www.visitannapolis.org/blog/stories/post/historic-annapolis-pub-crawl

Middleton Tavern