An ale maker was active in Milborne Port in the 16th century. The Ale House Act of 1551 would have required inns/alehouse to have been licensed in order to control “abuses and disorders as are had and used in common ale-houses”, to maintain good order in their houses and not to permit unlawful games. Unfortunately manuscript copies of the licenses for the area are indistinct, but by 1738 Milborne Port had seven licensed victuallers and by 1753 there were nine which were recorded on printed forms.
In 1746, one of the licensed victuallers kept The Tippler or Tippling Philosopher and in 1792 the licensee was George Davis Hyde. The property, which is over four hundred years old, was bought in 1797 by The Marquis of Anglesey from the trustees of Mr Noakes, a mercer, for £345 19s 8 3/4d. Major building work costing £424 14s 4 1/2d was carried out in 1798. A bundle of receipts include work by Thomas Hallett a carpenter for £125 7s 1 3/4d and £7 10s 8d paid to George Chislett, landlord, for liquor for labourers from Oct 1797 to Nov 1798.
The Tippler was renamed The King’s Head circa 1820 and was the venue in 1837 for a supper for a hundred local men, employed to work on alterations to Ven House, the seat of Sir William Coles Medlycott. In 1900 The Kings Head Hotel boasted good stabling and loose boxes for twenty four horses. The name later reverted to The Tippling Philosopher.
A more recent licence was granted to The Gainsborough Arms, which was built in 1866. There are references to orchards at Gaynsbury in 17th century Milborne Port wills, and those orchards, including Bauntons, still existed at the time, which was before Newtown was built. The lively pub offered accommodation and boasted a thriving skittle alley which was used for both skittle matches and public meetings which attracted capacity audiences. In 1928, the Parish Council gave permission for a letter-box to be erected nearby.