I spend a lot of time studying and writing about 18th century tavern keeping. Taverns of all kinds - from fancy inns to rough-and-tumble dockside establishments - played an important role in travel and social experiences in British North America. Some of those taverns survive today, including Middleton Tavern in Annapolis, MD.
History of Middleton Tavern (that most interests me)
According to the good folks at Middleton Tavern, the building likely was in use in the 1740s, but it was in 1750 that Elizabeth Bennet sold it to Horatio Middleton. In the years leading up to the Revolution, Horatio established what he called an "Inn for the Seafaring Men." This is an interesting business position to take. In early America, many taverns were reluctant to serve sailors (there were even laws against doing so), in part because they were especially transient and unreliable in paying for services rendered.
In addition to the tavern, Horatio created a ferry system to connect Annapolis to the Eastern Shore of the Chesapeake Bay. His ferrying expertise would be particularly useful in the winter of 1755. Around 900 Acadians (French-speaking Roman Catholics from Nova Scotia) arrived in the Chesapeake Bay. Although they had taken oaths required of British citizens, they refused to fight against their French and Canadian countrymen and were exiled. Annapolis residents were willing to provide some money and provisions as the suffering Acadians bobbed in the bay, but only to a point. Eventually, three of the ships sailed on, and Horatio helped ferry some of the passengers of the Leopard to Baltimore.
It's also possible that Horatio was forced to lodge British troops in the winter of 1757-1758. Approximately 500 soldiers were dispatched to Annapolis in late November 1757. They didn't want to be there and Annapolitans certainly didn't want them there, so no one was disappointed when they left in March 1758. At least 75 townspeople applied for government reimbursements for expenses associated with quartering the troops. Horatio Middleton appears to have requested a large reimbursement, but it's unclear whether or not he received what he requested.
When Horatio Middleton died, his wife Anne (or Ann, depending on the source) took over the tavern. Perhaps wise to the precariousness of tavernkeeping, Ann(e) chose to keep the ferry going and accepted boarders, but closed down the general tavern component of the business. When her son eventually took over, he expanded the business running the tavern, the ferry, a ship-building operation, and overseas trade.
Tavern Keeping in Maryland
Early Drinking Laws
Early Maryland laws impacting taverns focused on the act of drinking more than the business of tavern keeping. In 1642 fines were established for drunkenness, but it took more than a decade for tavern owners to feel the pinch. In 1654, liability was extended to anyone "who shall suffer drunkenness in their house." Even as late as 1674, laws focused specifically on drinking, including outlawing alcohol consumption on the Sabbath.
Eventually, Maryland recognized the need to maintain a network of safe and affordable taverns and inns. People were required to travel fairly far distances to shop at market days or attend court. Houses were few and far between, making travel hard and wearisome. Maryland lawmakers acknowledged that "divers persons are either exposed to great hazards of their health or much burdensome to particular adjacent Neighbors."  With that in mind, the General Assembly passed laws to protect travelers from tavern owners who attempted to overcharge for food and lodging.
Maryland did not create a licensing structure for taverns until the 1670s. Ordinary keepers were not averse to breaking the rules, whether that was serving alcohol to mariners or enslaved workers, charging exorbitant fees for lodging, or allowing prostitutes to work on their property. To help control this behavior, in 1674 the General Assembly authorized the Maryland governor to create and issue tavern licenses.
After decades of working to establish enough taverns and inns to support Maryland travel, the colony began changing its focus. By 1678, Maryland was actively limiting tavern ownership through its licensing laws.
Middleton Tavern in the Early American Republic
My interest in the tavern keeping is mainly focused on the years leading up to the American Revolution. During and after the Revolution, Middleton Tavern was a particular hotspot. Annapolis was the center of many important events including General George Washington resigning his commission in December 1783 and the ratification of the Treaty of Paris in January 1784.
In addition to George Washington, other Revolutionary luminaries including Tench Tilghman, Thomas Jefferson, and Benjamin Franklin patronized Middleton tavern, likely enjoying the delightful gardens and admiring the decorative art that graced the walls inside.
On June 1, 1970, a massive fire damaged the tavern so severely that what survived of the property was almost demolished. However, Annapolis recognized the commercial value of the tavern and its history and chose to rebuild and expand what remained. Today, boats can dock and hungry (recreational) sailors can hop off for a crabcake sandwich and chips. The tavern can accommodate events and large parties or just a bunch of folks getting together for a pint and a talk of the day. Not unlike in the 1750s, I suppose.
1) Sallinger, Sharon V. Taverns and Drinking in Early America, Johns Hopkins University Press, 2002, p. 91.
Additional Sources: Taverns and Drinking in Early America - Sharon V. Salinger