In 1897, Webster entered Vassar College as a member of the class of 1901. Majoring in English and economics, she took a course in welfare and penal reform and became interested in social issues. As part of her course she visited institutions for "delinquent and destitute children". She became involved in the College Settlement House that served poorer communities in New York, an interest she would maintain throughout her life. Her experiences at Vassar provided material for her books "When Patty Went to College" and "Daddy-Long-Legs". Webster began a close friendship with the future poet Adelaide Crapsey who remained her friend until Crapsey's death in 1914.