Upper School Outdoor Program Director
Milton Academy, Milton, MA
Summary of Position:
Milton Academy seeks a Director for the H. Adams ‘32 Carter Outdoor Program beginning in the fall of the 2025-26 academic year. This is a full time position and may include campus housing. The Director job is about ¾ of the workload of a full time position and therefore will ideally be combined with classroom teaching or other equivalent responsibilities. Part-time candidates may be considered but full time applicants will have priority.
Program Overview:
Founded in 1947 by mountaineer and skier Ad Carter, a Milton alum and later a teacher of modern languages at Milton Academy, the Program teaches rock/ice climbing, hiking/backpacking, sea kayaking and canoeing, and other outdoor skills in both an after-school program and through weekend and school break outings.
Students may elect into the after-school program in any of the three traditional sports seasons in fulfillment of their athletics requirement. The after school program offers outdoor rock climbing and hiking in the fall and spring, and indoor climbing in the winter. In the past, the program has offered sea kayaking in the fall and spring as an option as well.
The after school program offers weekend day, and occasional overnight, trips most weekends of the school year. The number and length of trips varies from month to month depending on the school schedule. We travel weekly to destinations as close as the Blue Hills (5 minutes away) and as far away as the White Mountain National Forest in New Hampshire. Most weekend trips are led by our in-house and adjunct instructors with occasional contract help from local guide services.
The program also takes advantage of spring and, ideally, in the future, summer breaks to run week-long trips that expose students to more in-depth experiences. In the past these trips have been domestic (Yosemite, Zion, Joshua Tree) and international (Belize, Baja, Bahamas, Costa Rica).
Position Overview:
The Director serves as a member of the teaching faculty of the Academy and oversees all aspects of the Program as outlined above and in the Essential Functions and Responsibilities and Competencies section below.
The ideal candidate will be a certified AMGA Single Pitch Instructor (or higher) and/or hold an ACA paddling certification and hold a WFA or WFR certification. The candidate will have previous experience leading wilderness trips, ideally with youth groups, have a wide range of outdoor skills, enjoy working with teenagers, and have a good sense of humor. We seek individuals who are flexible and are enthusiastic about working in a complex, academically rigorous boarding school.
We recognize that many applicants may not have the entire outdoor skill set outlined above or the combination of academic teaching and outdoor education experience. We seek either an individual who is well rounded in the outdoors OR an individual who has a high level of expertise in one area (climbing or paddling, for example) and the knowledge base to partner with adjuncts or contract guides for areas in which the individual has less expertise. Above all we seek a person who is passionate about the outdoors and about sharing that passion with students.
Milton Academy
