For over four decades, the federal Head Start program has provided millions of young children from impoverished backgrounds with access to early childhood education and basic health services. By some important measures, Head Start has helped put children on the path to academic and economic success. Teachers in the Head Start program play a crucial role in this process, by laying the foundation for preschoolers' future academic and social development. Recognizing this, policymakers and early childhood advocates have made improving the academic caliber of Head Start, and boosting the overall qualifications of the program's teaching staff, a priority. Yet many teachers and teacher assistants working in Head Start's migrant and seasonal and American Indian and Alaska Native (AIAN) communities--among the nation's most economically disadvantaged populations--face significant obstacles in pursuing college degrees and professional training. These obstacles include: (1) Lack of access to two- and four-year colleges in their rural and remote communities; (2) Difficulty transferring credits among those institutions; (3) Lack of year-round employment in teaching, where programs are seasonal; (4) An unfamiliarity with college processes and cultures; and in some cases, and (5) Lack of proficiency in English, which can make enrolling and succeeding in credit-bearing college courses extremely difficult. These teachers are a crucial, and yet underutilized resource within the Head Start community. Migrant and seasonal and AIAN Head Start teachers bring distinct cultural and linguistic backgrounds and skills--as well as an abiding passion and commitment--to their work with young children and families. Many of these teachers grew up in the Head Start communities they now serve. This paper describes the hurdles that teachers in these communities face in pursuing degrees and credentials; puts the challenges they face in context; and offers promising practices and recommendations that can strengthen this teacher corps and build the Head Start program's cultural and linguistic expertise. Individual sections contain footnotes.