The Sherwood Windows were designed based on suggestions made by Martha Hale Shackford, class of 1896, and later Professor of English Literature, and created by Joseph G. Reynolds of Reynolds, Francis, and Rohnstock in 1958. The Central concept of the windows is derived from the poem, The Pilgrim, written by Professor of English, Sophie Jewett, to her friend and fellow professor Margaret Sherwood, Class of 1895 and Professor Emeritus of English Literature (1889-1931) at Wellesley College.

The Pilgrim

Pilgrim feet, pray whither bound?

Pilgrim eyes, pray whither bent?

Sandal-shod and travel-gowned,

Lo, I seek the way they went

Late who passed toward Holy Land.

The center window depicts a figure of a female pilgrim and the indication of a medieval fortified town, a symbol of a pilgrimage to faraway places. Beneath the pilgrim, three angels are featured, signifying philosophy, nature, and theology. The figure in the left window is a representation of St. Catherine of Alexandria, noted for her wisdom, and flanked by symbols of her martyrdom. The prendella beneath the left window depicts St. Catherine and the doctors of Maxentius. The right window features St. Brendan of Confert, and several of his attributed symbols. His prendella is a depiction of St. Brendan's voyage to the Land of Promise of the Saints.