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The firm that was eventually to become Miles Madeira was originally known as Rutherford & Brown, established on the Island of Madeira in 1814.

In 1856 Henry Price Miles left England with his family and arrived in Madeira. Having worked as an apprentice since the age of 12 under the tutelage of James Rutherford, he acquired sound knowledge and experience of the workings of the Madeira trade. In 1872 the Rutherfords left for London (due to Phylloxera which decimated most of the vineyards in Madeira) and started up a wine importing business at the Old Trinity House in Waterlane. This prompted Miles to purchase the company and stocks and he later made a gentleman's agreement with Rutherford that any Madeira sold by them in the United Kingdom, Scandinavia, or Russia would be bought through H.P.Miles and Co. This agreement was respected and carried on until the Rutherfords sold their firm Rutherfords, Osborne and Perkins to Martini Rossi in the 1960's.

Together with the wine production, H.P.Miles created the first brewery in Madeira in 1872 called the "Atlantic Brewery". It was in these two companies that he and his 2 sons, Henry Alfred and Charles Vaughan created the Miles legacy on the Island.

After the end of World War II, conditions in the wine trade became extremely difficult and Henry Alfred Miles' son, Cecil Miles negotiated the entry of H.P.Miles and Co. into the Madeira Wine Association. All the wine stocks and buildings were incorporated into the M.W.A and today the actual Madeira Wine Company's bottling plant is situated in the old Miles' adega at Largo da Saude. One of the lodges continues to be used exclusively for the ageing and maturation of the Miles' Frasqueira-Vintages and older blended wines.

Miles Madeira is synonymous with excellent wine and has become one of the best known and most respected brands in the world.