She participated with Crapsey in many extracurricular activities, including writing, drama, and politics. Webster and Crapsey supported the socialist candidate Eugene V. Debs during the 1900 presidential election, although as women they were not allowed to vote. She was a contributor of stories to the "Vassar Miscellany" and as part of her sophomore year English class, began writing a weekly column of Vassar news and stories for the "Poughkeepsie Sunday Courier". Webster reported that she was "a shark in English" but her spelling was reportedly quite eccentric, and when a horrified teacher asked her authority for a spelling error, she replied "Webster", a play on the name of the dictionary of the same name.