Rick Rege arrived at his job as superintendent of his western Massachusetts school district the way most folks do--advancing from classroom teacher to mid-level administrator to the district's top position. In Rege's case, he spent the nine years before becoming superintendent of the Chicopee Public Schools as a middle school vice principal and principal. He knew how to manage people and oversee a budget. He didn't figure leading the district would be much of a change. Yet quickly after his appointment in summer 2005 to the superintendency in the district just north of Springfield, Massachusetts, the blush wore off as Rege realized the enormity of the task facing him. Lucky for Rege he lives in Massachusetts. His state superintendents' association has a tried-and-true mentoring program for new superintendents. From periodic meetings with other new superintendents to one-on-one sessions with his mentor, a former longtime superintendent in the state, Rege has felt supported and confident in his new role. Over the last several years, an increasing number of state-level professional associations have begun offering novice superintendents the chance to learn from those who've gone before. While some leaders over the years informally sought out experienced colleagues willing to offer advice, the current programs formalize the tradition, give it a name and acknowledge the practice's value. The superintendency may be the final frontier for formal mentoring programs. In the 1990s, teacher mentoring programs proved that supporting first-year teachers yielded better instructors who stayed longer. That success led to programs for building principals. Now mentoring programs are trickling up to superintendents, who by definition are the instructional leaders of their school districts. This article takes a look at three longstanding programs (Massachusetts, Texas, New Jersey) and at three programs just getting off the ground (California, Iowa, Alaska).