There are countless stories of Jewish life in Maine, stretching back 200 years. These are stories worth telling not only for their enjoyment value but also because we can learn a great deal from them. They reflect the challenges that confronted members of an immigrant community as they sought to become true Mainers, as well as the challenges this ethnic group now faces as a result of its successful integration. The experiences of Jews in Maine, moreover, encapsulate in many ways the experiences of small-town Jews throughout New England and the United States. Their stories offer glimpses into the changing nature of American Jewish life and also point toward significant continuities in life outside of America’s major Jewish population centers. This essay weaves together representative stories to trace the history of Jewish life in Maine and, by extension, small-town America. The stories collectively tell a tale of “making it”: an ongoing process of striving for success in the face of shifting obstacles and opportunities. Many of the stories recounted here were gathered by students involved in Colby College’s Maine Jewish History Project, an ongoing research effort focused primarily on Colby’s hometown of Waterville and on the surrounding Kennebec Valley.