Sherwood Anderson is highly skilled in portraying grotesques distorted by the industrialized society. This paper is to unfold the repression and inner struggle of the two typical spinster images in the novel Winesburg Ohio, the masculine small town, which entraps women with the conventional codes. They achieve economic independence in their earlier years which is their first attempt to overthrow the yoke of man-dominated world. They employ different means to release the deep buried passion and eagerness to love and to be loved so that they can shake off loneliness and repression. However, in the climatic moments, they fail in their seek for self-fulfillment and are doomed to be tossed between traditional women roles and modern awakening.