Vermont, which became our 14th state on March 4, 1791, was the first to be added to the original 13 colonies. However, the American flag was not changed until 1795, three years after the addition of Kentucky, in 1792. Because the union was comprised of 14 states for a period of only 15 months, 14 was never an official star count. For this reason--combined with the extreme scarcity of 18th-century Stars & Stripes, in general--only a small number of American flags with 14 stars are known to exist from this period.
The flag pictured above is most likely from the late 19th century. Flags during this period were usually created for use in celebrations and special events, such as the 100-year anniversary of Vermont statehood in 1891, the 1876 World's Fair Centennial Exhibition, or the 1893 Chicago World's Fair. However, some flag historians believe that some may have simply been made by mistake, the designer having intended to incorporate only 13 stars.
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All flag images are used courtesy of Jeff R. Bridgman American Antiques, LLC, and remain © Jeff R. Bridgman American Antiques, LLC.