The Haunted History of Middleton Tavern, Annapolis, Maryland

Nestled in the heart of historic Annapolis, Maryland, Middleton Tavern is more than just a charming spot for dinner or a drink—it’s a site steeped in centuries of history and, according to legend, haunted by restless spirits. Dating back to 1750, this colonial-era tavern has served as an inn, general store, meat market, and even a ferry stop. Over the years, tales of unexplained phenomena have made it one of the most talked-about haunted sites in Annapolis.

A Tavern With Deep Roots

Horatio Middleton opened the tavern in the mid-18th century, catering to sailors and travelers who docked along the Annapolis waterfront. The building has seen its share of renovations and fires, including significant restorations in the 1970s, but its historic charm remains intact. With its centuries-long history, it’s no surprise that stories of lingering spirits have become part of its lore.

The Ghosts of Middleton Tavern

Roland Johnstone: The Mischievous Colonial Spirit

The most famous ghost at Middleton Tavern goes by the name Roland Johnstone. Described as a middle-aged man in Revolutionary-era clothing, Roland is known for his mischievous (and sometimes malevolent) behavior. Staff and visitors report the smell of cigar smoke appearing out of nowhere, objects being knocked off shelves, furniture moving on its own, and even electronic devices acting strangely.

Some have seen Roland crossing the bar in full colonial attire, vanishing before reaching the other side. The second floor and upper areas of the tavern are rumored to be particularly active, with some staff too frightened to venture upstairs alone.

Shadowy Figures and Other Entities

In addition to Roland, guests and employees have reported seeing shadowy figures gliding through the dining rooms, and lanterns mysteriously flipped upside down. Tables and chairs have reportedly moved on their own, adding to the tavern’s reputation as a hotspot for paranormal activity.

George Schmidt: The Tragic Tale

Another ghost tied to Middleton Tavern may be George Schmidt, a man who was allegedly killed outside the tavern during an argument in 1876. Some lore suggests that Schmidt’s spirit, or perhaps Roland himself, is responsible for certain disturbances, particularly the more aggressive poltergeist-like activity.

Paranormal Experiences

Staff and tour guides have shared numerous accounts of unexplained events. Some nights, coffee is spilled in the upstairs kitchen without explanation, silverware moves on its own, faucets turn on and off, and lights flicker mysteriously. Guests and employees alike report a sense of being watched, and some have even felt phantom touches. Many of these incidents occur in the early morning hours when the tavern is quiet and the shadows long.

Why Middleton Tavern Captures the Imagination

Middleton Tavern’s long and varied history, combined with these reports of supernatural activity, has made it a fixture on Annapolis ghost tours. Whether you’re a skeptic or a believer, the stories of Roland, shadowy figures, and unexplained disturbances add an eerie charm to this historic landmark. Its haunted reputation is as enduring as its colonial architecture, making a visit here an experience that blends history, mystery, and a touch of the supernatural.