Cigar Smoke on the Balcony: The Middleton Tavern Ghost

Reviewed by Josh N · Updated September 29, 2026 · How we verify

Ask around the Annapolis waterfront and you will hear about the Middleton Tavern ghost before you hear much about the food. The building is a working tavern in Maryland’s capital, one of the oldest continuously operating taverns in the United States, and the stories attached to it are folklore rather than documented event. That distinction matters here, because the history alone is substantial enough without the embellishment.

Horatio Middleton’s Inn for Seafaring Men

The tavern was established in 1750 by Horatio Middleton and began life as an inn catering to seafaring men, which is about what you would expect from a house standing this close to the harbor. After Horatio died, his son Manuel took over the business. The guest list from those decades is the part locals repeat most often: George Washington, Thomas Jefferson, Benjamin Franklin and members of the Continental Congress were all known to frequent the place.

The Middleton family kept a hand in the property well past the Revolution. Through the 1800s the family business expanded to include a general store and a meat market. Later the Mandris family bought it and ran a restaurant and a souvenir shop out of the building. In 1968 Jerry Hardesty purchased the property and restored the Middleton Tavern name, which is the name it carries now.

Roland, and the Man Killed Out Front in 1876

Local folklore holds that a ghost haunts the tavern, and the most commonly repeated sign of him is not a sighting at all but a smell: cigar smoke drifting along the upper balcony with no source. Staff have given the entity a name, Roland, and some describe him as dressed in Revolutionary-era clothing. There is no record identifying any historical person behind the nickname, and the description appears to come from the staff and regulars rather than from any document.

A competing local theory points to a real death. George Schmidt was killed in front of the building in 1876, and some accounts attribute the activity to him instead. The two explanations sit awkwardly together, since one imagines a figure in eighteenth century dress and the other a man who died more than a century after the tavern opened. Neither has been substantiated, and both are best understood as stories the house has accumulated rather than conclusions anyone has reached.

Three Stories of Brick and a Wall Full of Muskets

The tavern itself is a three-story brick structure built in the Georgian style. Inside, the decor leans hard into the building’s age: the walls are hung with Civil War muskets and antique naval uniforms. It is the kind of interior that does half the atmospheric work before anyone mentions a ghost, which is worth keeping in mind when you are sitting in a dim eighteenth century room deciding whether that smell is a cigar or the guy at the next table.

Visiting Middleton Tavern in Annapolis

Middleton Tavern is an operating tavern and restaurant, so the simplest way to see it is to walk in, sit down and order something. No ghost tour is required for that. The tavern does, however, appear on a number of ghost tours covering the Chesapeake Bay watershed region, and those are the easiest route if you want the folklore narrated rather than pieced together from the staff. The upper balcony is where the cigar smoke reports cluster, though nothing about the place is presented to visitors as haunted in any official sense.

Address: Annapolis, Maryland

See Middleton Tavern for Yourself

Sources

• Historic businesses in every state
• Middleton Tavern
• Middleton Tavern in Annapolis, USA
• Where's Marty? Discussing who the ghost of Middleton Tavern might be – CBS Baltimore
• Middleton Tavern featured on ‘The Ghost in My Room’ podcast
• Wikipedia: Middleton Tavern

Ghost Tours Nearby

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