Annapolis, Maryland · Founded 1750
An Annapolis City Dock restaurant with a 1750 inn-and-ferry origin, a Founding-era patron tradition, and a revived historic name.
Middleton Tavern occupies a historic City Dock property associated with Horatio Middleton's 1750 inn for seafaring travelers and his ferry route to Maryland's Eastern Shore. Its history includes periods as a tavern, general store, butcher shop, provisioner and restaurant rather than a proven uninterrupted tavern operation. Jerry Hardesty bought and restored the business in 1968, returning it to the Middleton Tavern name.
Later histories say the building was probably or likely occupied by this time, when Elizabeth Bennett owned the property; this is an occupancy estimate, not a verified construction date.
Source: Middleton Tavern, "About"; Patch, "Middleton Tavern Building Sold To Naval Academy Graduates For $3.3M," May 3, 2023
Elizabeth Bennett sells the property to Horatio Middleton, who operates an inn for seafaring travelers and a ferry service between Annapolis and Rock Hall.
Source: National Trust for Historic Preservation, "Historic Bars: Middleton Tavern in Annapolis, Maryland," September 9, 2015; Middleton Tavern, "About"
Tench Tilghman travels via Middleton's ferry while carrying news of Cornwallis's surrender, according to the National Trust's historical account.
Source: National Trust for Historic Preservation, "Historic Bars: Middleton Tavern in Annapolis, Maryland," September 9, 2015
Thomas Jefferson uses Middleton's ferry on a trip toward Rock Hall, according to accounts of the tavern's ferry history.
Source: National Trust for Historic Preservation, "Historic Bars: Middleton Tavern in Annapolis, Maryland," September 9, 2015
Jerry Hardesty purchases and restores the business, returning it to the Middleton Tavern name after a period that included the Mandris Restaurant.
Source: National Trust for Historic Preservation, "Historic Bars: Middleton Tavern in Annapolis, Maryland," September 9, 2015; Middleton Tavern, "About"
Hardesty expands the restaurant to include a new Tavern and Oyster Bar.
Source: National Trust for Historic Preservation, "Historic Bars: Middleton Tavern in Annapolis, Maryland," September 9, 2015
Annapolis Capital Partners, associated with Cody Monroe and Clinton Ramsden, purchases the building housing Middleton Tavern; the new property owners say the tavern remains a tenant and they will not manage it.
Source: Patch, "Middleton Tavern Building Sold To Naval Academy Graduates For $3.3M," May 3, 2023
Every claim gets rated. A business's own website can never earn "documented."
The National Trust and the tavern's current historical account agree that Elizabeth Bennett sold the property to Horatio Middleton in 1750 and that he operated an inn connected to his ferry service. This review did not inspect the underlying deed, ferry license or inn license.
The National Trust and the tavern's official historical account identify Washington, Jefferson and Franklin as prominent patrons, and the National Trust provides a specific 1783 Jefferson ferry connection. The candidate's claim that Washington's diaries and tavern ledgers confirm repeated meals and meetings was not verified in this review.
The property has a long history of hospitality and commercial use, but available accounts say it also functioned as a general store, butcher shop and provisioner and that Jerry Hardesty restored the Middleton Tavern identity in 1968. The sources reviewed do not establish uninterrupted tavern operation from 1750 to the present.
The National Trust describes Horatio Middleton's ferry service between Annapolis and Maryland's Eastern Shore, and the official tavern history identifies Rock Hall as the route's eastern endpoint. The claimed ferry operation is credible, though its original license was not reviewed.
Patch reported that Annapolis Capital Partners, associated with Cody Monroe and Clinton Ramsden, purchased the building in 2023. The purchasers said Middleton Tavern would remain a tenant and that they would not manage its restaurant operation.
Maryland tourism and the restaurant's active site list Middleton Tavern at 2 Market Space, Annapolis, with current restaurant contact information and hours.
Thomas Middleton founded Middleton Tavern in 1750.
The reviewed histories identify Horatio Middleton, not Thomas Middleton, as the person who bought the property from Elizabeth Bennett in 1750 and operated the inn and ferry service.
Source: National Trust for Historic Preservation, "Historic Bars: Middleton Tavern in Annapolis, Maryland," September 9, 2015; Middleton Tavern, "About"
The Middleton Tavern building was constructed circa 1750.
The sources reviewed say the property was probably or likely occupied as early as 1740. They establish 1750 as Horatio Middleton's purchase and inn-operation date, not as a verified construction date.
Source: Middleton Tavern, "About"; Patch, "Middleton Tavern Building Sold To Naval Academy Graduates For $3.3M," May 3, 2023
Middleton Tavern has operated continuously as the same tavern since 1750.
The property has served as an inn, ferry-related business, general store, butcher shop, provisioner and restaurant. Jerry Hardesty restored the Middleton Tavern name in 1968, and the reviewed sources do not document uninterrupted tavern operation.
Source: National Trust for Historic Preservation, "Historic Bars: Middleton Tavern in Annapolis, Maryland," September 9, 2015; Middleton Tavern, "About"
Jerry Hardesty owns the historic tavern building.
Patch reported that Annapolis Capital Partners purchased the building in 2023 and that Middleton Tavern would remain a tenant. The reported restaurant operator and property owners are distinct.
Source: Patch, "Middleton Tavern Building Sold To Naval Academy Graduates For $3.3M," May 3, 2023
Middleton Tavern has endured as a waterfront hospitality address by adapting to Annapolis's changing commercial life. Its historical identity rests on the ferry-era inn, its location near the State House and City Dock, and a late-twentieth-century restoration of the Middleton name. It remains active as a restaurant tenant in a building separately acquired by Annapolis Capital Partners in 2023.
Middleton Tavern traces its beginning to 1750, when Elizabeth Bennett sold the City Dock property to Horatio Middleton. The National Trust says Middleton used it as an inn for seafaring travelers connected to his ferry route between Annapolis and Maryland's Eastern Shore.
Middleton Tavern and the National Trust list George Washington among the tavern's prominent historical patrons. The available sources support a longstanding association, but this review did not verify the candidate's claimed Washington diary entries or tavern ledgers documenting multiple meals.
The National Trust reports that Thomas Jefferson used Middleton's ferry on a trip toward Rock Hall in 1783. That provides a specific documented historical connection to Middleton's City Dock operation, though it does not by itself establish how often Jefferson dined at the tavern.
Middleton Tavern is frequently described as one of America's oldest continuously operating taverns. The sources reviewed support a long history of hospitality and commerce at the property, but they also document changing uses and a 1968 revival of the Middleton Tavern name, so uninterrupted tavern operation has not been independently established.
The building that houses Middleton Tavern was purchased in 2023 by Annapolis Capital Partners, associated with Cody Monroe and Clinton Ramsden. Patch reported that the purchasers would not manage the restaurant, which remained a tenant under a multi-year lease.
Jerry Hardesty is the person identified in historical accounts as having bought and restored the Middleton Tavern business in 1968. This review did not locate a current Maryland business filing or liquor-license record naming the present legal restaurant operator, so the precise current operating entity remains unresolved.
2 Market Space, Annapolis, MD 21401
(410) 263-3323
Check the restaurant's current menu, reservations and hours before visiting; the business operates in the City Dock building as a restaurant tenant.