The Tavern was originally located on Court Street across Highland Street from the
Dedham Inn. The original proprietor in 1749 was Benjamin Gay, who built it into an establishment as nice or nicer than any other in the area. Benjamin and
Nathaniel Ames of the
Ames Tavern had a rivalry, with Ames once writing in the
Ames Almanack that people should not believe the rumors Benjamin was spreading about his establishment. Slightly north of Gay's Tavern, at the intersection of Court and Church Street, was Howe's Tavern. In those days,
stagecoaches would stop at the various taverns along the route for a change of horses or refreshments. In the early days, as many as 20 stagecoaches a day would pass by the house, with many stopping at Gay's Tavern. The arrival of the coach was always a lively one at Gay's Tavern. The townsmen eager for the latest news would drop in and mingle with the new arrivals around the comfortable fire in the great room. Here the assembled company would discuss all manner of subjects, with politics usually being the chief topic. After Benjamin died in 1761, his widow ran the Tavern. Following her death, her son Joshua Gay ran the Tavern. Joshua kept the Tavern for more than 25 years until his death, at which point Timothy Gay of Needham became the owner and proprietor. The Tavern was a sort of political headquarters for years during this era. Shortly after the
Constitution of Massachusetts was adopted on October 25, 1780, a number of towns in
Suffolk County, of which Dedham was a part, elected delegates to a convention to decide upon some policy relative to the division of the county. The convention met at Gay's Tavern on December 12, 1780, and adopted a resolution to the effect that the towns of
Bellingham,
Dedham,
Foxborough,
Franklin,
Medfield,
Medway,
Needham,
Stoughton,
Stoughtonham,
Walpole, and
Wrentham, along with the
Middlesex County towns of
Holliston,
Hopkinton,
Natick, and
Sherborn ought to be formed into a new county with Medfield as the shiretown. The
Great and General Court did not look favorably upon the resolution, however, and
Norfolk County was not created until 1793, with Dedham as the shiretown. Following the creation of
Norfolk County, Gay's Tavern was the site of a Court of General Sessions on August 25, 1794. They ordered that the committee on buildings proceed with collecting materials for building a jail. On the last day of September following this order, the court accepted from Timothy Gay the gift of a parallelogram lot of land to erect the
Norfolk County Jail next to his tavern. ==Second location==