During a speech on "Genealogical Sources of the Philadelphia Area" delivered at the National Genealogical Society in March 1962, Walter Lee Sheppard, Jr., remarked parenthetically that there seemed to be lineage societies for all kinds of ancestors except tavern-keepers. Kenn Stryker-Rodda suggested from the audience, "Let's found one." Enough people heard of the idea to prompt Kenn's sending a letter dated 1 September 1963 suggesting "an annual dinner at an old inn, with colonial menu (solid and liquid) spiced with learned and witty addresses on suitable topics, as the focus for the Society." It was Sheppard who dubbed the organization "Flagon and Trencher."

Sheppard and Stryker-Rodda were surprised by the response, but saw the feasibility of creating an organization that would not be bound by the usual rigid rules and regulations of other organizations, but would make it possible for interested persons to establish their ancestry from a tavern- inn, or ordinary-keeper who was in business during the colonial period.

The December 1963 issue of the National Genealogical Society Quarterly carried an announcement stating the requirements for membership. In the two years that followed, many applications were received. Although it was suspected by Sheppard and Stryker-Rodda that membership would probably be small, by early 1965 it became evident to them that there was more interest in the Society than initially anticipated.

The first dinner meeting was held on 21 May 1965 at Fraunces Tavern in New York City. At that time, there were 20 charter members and 32 other qualified members, whose applications had been carefully checked. More than half of the members attended the meeting. It was at this meeting that the name of the Society was formally chosen by its membership. It was also decided that a different host, with the title of "Mine Host," would be chosen for each future annual meeting. A constitution and by-laws were drafted soon thereafter, based on the many suggestions of the membership.

The second meeting was held 20 May 1967, at which time the constitution and bylaws were adopted, and a design for the Society's insignia was chosen. The name of the Society became "Flagon and Trencher: Descendants of Colonial Tavern Keepers." The insigne is a tavern sign bearing the design of a flagon and a trencher with two wooden spoons and the name "Flagon and Trencher."

By 1973, there were more than 75 members, nearly half of whom attended the annual meeting at General Wayne Inn in Narbeth, PA. This meeting marked the beginning of an even greater interest in the Society, for in that year alone, 35 new members were added. In 1974, the membership increased by 42 more, and in the year 2002, the Society reached a membership of more than 1,000. All told, the Society's members have numbered nearly 2,300; more than 600 supplemental applications have been filed, and the membership thus far recognizes more than 5,000 colonial tavern-keepers and inn-keepers.

Throughout this growth, the Society has been led by a remarkably small number of officers.

In the year 2002, Alexander Bannerman, only the third person to hold the office of Keeper of the Tavern Records in the Society's history, developed three special-recognition awards. The first, known as the Flagon Award, is an engraved pewter flagon, awarded to a member who has contributed substantially to the growth and maintenance of the Society for 10 years or more. The second, known as the Trencher Award, is a lapel clutch-pin in the design of a trencher, awarded to individuals who serve as Mine Host for an annual meeting, or who in some other way provide a valuable service to the Society. Both awards are accompanied by a certificate of appreciation. The third award is a carved wooden plaque bearing the Society's emblem, and is occasionally presented in gratitude to the Tavern or Inn that hosts an annual meeting of the Society.