Literal. The road is laid out on the south or sunny side of the ridgeway. The name may have been inspired by the growing popularity of the use Sunnyside as a house name, writing in Sunnyside: A Sociolinguistic History of British House Names, Dr Laura Wright, a linguist at Cambridge University, explains that the name goes back to the Nordic practice of solskifte, a prehistoric method of dividing up land according to position of shadows. Its popularity as a house name began with Washington Irving, the American author of Rip Van Winkle and The Legend of Sleepy Hollow, who was a contemporary Sir Walter Scott, of Ivanhoe fame. When Irving visited Scott at Abbotsford, the palatial house that he had developed out of an old farm called Clarty Hole, near Melrose Abbey, he was taken on walks around the area. “Sunnyside was the name of a picturesque stone steading close to Abbotsford that I presume Irving saw on his rambles with Sir Walter”, Wright explains, adding that this was why, when Irving could afford to create his own version of Abbotsford, he called it Sunnyside. It’s an idea confirmed in a letter he wrote to Scott declaring “there is a genial sunshine about you that warms every creeping thing into heart and confidence”. The name gained in popularity in America after 1859 when Oliver Wendell Holmes described Irving’s property as “next to Mount Vernon [George Washington’s home] the best known and most cherished of all the dwellings in our land.” The name criss-crossed the Atlantic and became popular in London among rich industrialist Nonconformists (especially Quakers) with Scottish family ties in the 1870s for their own grand suburban residences.
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