On a countryside hill in Middlebury, Connecticut, stands Highfield, the estate designed by pioneering architect Theodate Pope Riddle (1867–1946) for Joseph and Elizabeth Chamberlain in 1911–1914. By the time of the commission, Pope was starting to make a name for herself. Despite a lack of formal architectural training, she designed schools and homes throughout Connecticut, retaining only her maiden name “Pope” in her professional pursuits, and challenging the era’s gender stereotypes along the way. In 1918, she became one of the first five women admitted to the American Institute of Architects, the most prestigious professional organization in the field, and in 1933, one of the first licensed female architects in Connecticut. This exhibition celebrates Pope’s steadfast nature and the beauty of Highfield through family-album photographs from the Chamberlains’ earliest years in residence there and material related to Pope’s English Arts & Crafts–style design.