Associate Director of Trips chez Chewonki

Do you light up when talking about expedition planning, field leadership, and the growth that happens on trail? Are you the kind of leader who can motivate a team, manage logistics, and model best practices in both safety and joy?

Chewonki is seeking an inspiring and detail-oriented Associate Director of Trips (ADT) to oversee one of the most defining components of our legacy—fun, safe, and transformational wilderness expeditions. Reporting to the Director of Camp Chewonki, this role combines program leadership, curriculum development, seasonal staff management, parent communication, and community culture-building into one deeply rewarding position.

• Location: Wiscasset, Maine

• Reports to: Director of Camp

• Schedule: 3/4time, Year-Round (January - October; Off November and December)

  • Anticipated Start Date January 5, 2026

  • Summer (June - August): Residential Position (Housing Provided; This position is required to reside on campus during the Summer Season)

• Salary: $48,880/Annually 

• Benefits:  Seasonal housing, meals on campus, health insurance, dental insurance, vision insurance, life insurance, 403B retirement plan, and access to professional development funds.

• How to Apply?

  • Submit Application, including Cover Letter 

  • Deadline to Apply: November 10th, 2025 at 11:59pm

Key Responsibilities

• Program Leadership

  • Manage all operational aspects of Camp Chewonki trips and expeditions during the summer season.

  • Provide direct field support to Trip Leaders and serve as 24/7 on-call contact when programs are in the field.

  • Oversee challenge course training, facilitation, and rescue procedures.

  • Plan and facilitate Trip Leader training, ensuring alignment with industry standards, local protocols, and American Camping Association (ACA) requirements.

  • Maintain high standards of safety, risk management, and program documentation.

• Curriculum and Program Development

  • Develop and refine integrated, developmentally appropriate curriculum aligned with Chewonki’s mission and DEI principles.

  • Collaborate with camp leadership to create progressive skill-building pathways across in-camp and backcountry programming for ages 8–18.

  • Update curriculum to include leadership, social and emotional learning, environmental context, and technical backcountry skills.

• Staff Hiring and Supervision

  • Recruit, hire, and onboard Trip Leaders and Adventure Staff in collaboration with the year-round hiring team.

  • Conduct interviews, reference checks, and placement decisions.

  • Develop staff schedules, task delegation, and time-off systems.

  • Provide ongoing mentorship through observations, feedback, and check-ins.

• Family and Partner Communication

  • Serve as a primary point of contact for camp families, providing clear and proactive communication regarding trip expectations and logistics.

  • Assist with camper recruitment, re-enrollment, and grant-supported access initiatives.

  • Coordinate with internal departments to ensure smooth transitions and high-quality participant experiences.

• Community Leadership

  • Contribute to a collaborative, inclusive, and mission-aligned staff culture.

  • Participate in risk management practices, shared responsibilities, and campus-wide events.

Qualifications

• 21 years of age or older

• 1–2 years of supervisory or leadership experience in outdoor education, residential camping, or related fields

• High school diploma or equivalent required; Associate’s or Bachelor’s degree in related field, preferred.

• Must pass Criminal Background Check including Motor Vehicle Record and Driver’s License approved by Chewonki’s insurance carrier.

• Prior trip leading or expedition-based programming experience

• Strong staff mentorship, logistics coordination, and communication skills

• Competent with Google Workspace and program management systems (e.g., CampMinder)

Required or Willing to Obtain Certifications:

• Wilderness First Responder

• ACCT Level 2 Challenge Course Practitioner Certification

• Maine Guide License

• American Canoe Association Instructor Certification

• Maine State Camp Trip Leader Instructor Permit

Physical and Scheduling Requirements

• Ability to lift up to 50 lbs and work in outdoor environments under varying conditions

• Ability to maintain a flexible schedule including evenings, early mornings, and weekends

Summer schedule follows a 6 days on / 1 day off rotation