Maryland's Oldest Continuously-Operating Tavern, Established 1750
2 Market Space, Annapolis, MD 21401
Research updated May 2026
Age
All Ages dining; 21+ at the bar
Cost
$$$
Sit-down restaurant with full menu and bar. Pricing typical of Annapolis waterfront dining.
Access
Wheelchair OK
Historic building with some uneven floors; ground-floor dining accessible
Equipment
Photos OK
Est. 1740 · Colonial Era · Founding Fathers Patronage · Maryland's Oldest Tavern · Annapolis Waterfront
The building at 2 Market Space in Annapolis was constructed in 1740 as a private residence and sold in 1750 to Horatio Middleton, who operated the Annapolis-Rock Hall ferry from the adjacent dock. Middleton converted the property into a tavern and inn serving ferry passengers and townspeople, establishing what would become the oldest continuously-operating tavern in Maryland.
The Annapolis-Rock Hall ferry was a primary connecting link between Annapolis and the route north to Philadelphia in the colonial and federal periods. Documented patrons from Middleton Tavern's records and surviving correspondence include George Washington, Thomas Jefferson, and Benjamin Franklin, who passed through Annapolis repeatedly during the Continental Congress years. Members of the Maryland Jockey Club met at the tavern, as did local Masonic lodges. President James Monroe is believed to have visited around 1818.
After Horatio Middleton's death, his wife and son Samuel continued the tavern and ferry business through the late eighteenth century. In the nineteenth century the property changed ownership and was for a period renamed the Mandris Tavern. In 1968 Jerry Hardesty purchased the building, restored it, and restored the original Middleton Tavern name. The restaurant is profiled by the National Trust for Historic Preservation as one of the country's significant surviving historic bars.
The building has been continuously serving food and drink in some form since 1750 and remains in operation as a full restaurant and bar at the Annapolis waterfront.
Sources
Middleton Tavern's haunting lore centers on a single figure that staff have come to call Roland. Multiple servers and bartenders interviewed for regional ghost-tourism profiles and a CBS Baltimore feature describe a male figure in revolutionary-era dress observed at the harbor-facing windows in the early morning hours before the restaurant opens. The apparition is most consistently associated with the second-floor dining room facing the dock.
A distinct sensory cue, reported across decades of accounts, is the smell of cigar smoke in spaces where no patron is smoking. Staff have associated the smell with Roland's presence and with the periods when plates and glasses on shelves topple without apparent cause. CBS Baltimore's coverage interviewed Hardesty family members and staff who described a table of empty dinner plates falling as a group on one occasion and lanterns mounted on the walls found inverted on another.
Identity attribution for Roland varies across retellings. Some accounts associate him with a colonial-era ferry passenger; others with a Middleton family member. None of these identifications is documented in surviving records, and Hauntbound treats them as oral tradition. The phenomena themselves are reported consistently across multiple staff generations and have been the focus of regional paranormal investigations.
The tavern is a routine stop on Annapolis Ghost Tours and US Ghost Adventures itineraries, where it is presented alongside other Annapolis historic-district sites including the state house and the Maryland Inn.
Notable Entities
Media Appearances
Dine in a 1740 waterfront building that has continuously served food and drink since 1750. The tavern's window seats face Annapolis harbor — the same view that staff have associated with the apparition known to regulars as Roland, a male figure in revolutionary-era dress reportedly seen most often in the early morning. The smell of cigar smoke without an obvious source is the recurring sensory cue.
Every HauntBound history is researched from documented sources. We clearly separate verified historical fact from paranormal folklore.
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Annapolis, MD
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Baltimore, MD
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