Winifred was financially independent, having been left £4000 by her father, Cuthbert. We have records of many of her purchases, including books by Voltaire, magazines, parchment, fabrics and art supplies. One of her largest purchases was a marble chimneypiece tablet of Aesculapius/Asclepius and Hygeia sacrificing to the Gods purchased in 1768 and carved by William Collins (fl. 1721-1793). As aesclepius was the Greek god of medicine, this plaque may have been a subtle reminder from Winifred to her gouty brother to be careful what he consumed in this grand and opulent space!
In her early twenties Winifred travelled independently to visit family and attend events in Scarborough. From 1762 to 1763 she and William rented a house in York for the ‘Season’.
William and Winifred met famed philosopher and writer Rousseau at Lyons in 1770. Rousseau appears to have been enormously impressed by Winifred, whom he ‘gallanted’ and whose ‘complaisancy and conversation’ earned high praise. William appears to have felt somewhat overshadowed; in a letter to his brother Marmaduke, he wrote that 'of her character he judged right, not so mine'. William's letters to Rousseau are an invaluable resource, giving further hints about Winifred's education (which allowed her to understand spoken French but not speak it) and about her interests ('neither the Great Character of Monsieur Rousseau nor several of his Masterpieces are unknown to her'). Perhaps one of the greatest gifts of these letters is, however, the direct expression of William's regard for his beloved sister. He describes Winifred to Rousseau as 'my Sister who attached herself to my Destiny, from my ardent Youth with a Fidelity, Constance and Love which have no Example'.
After touring France and Italy, William and Winifred went to Rome, where William busied himself buying art and antiquities. Rome was both a scholarly and a fashionable city in the 18th century. William described Winifred as looking ‘wonderous wise & somewhat happy’ having won £23 in cards- £2000 today! Rome in the 1770s was also home to the men of the failed Scottish Jacobite uprising of 1745, whose presence William seemed to scorn. He said he had ‘often seen the men of the 45, the Baron de Renfrew, the Pretender. He came up to your sister at a masked ball, a contemptible poor creature. His brother worse, narrow-minded, mean, dirty.’ Clearly, not the sort of titled acquaintance William was seeking!