Island Caretaker Jobs – Jewell & Little Chebeague Island, Maine – 2026 Season

CASCO BAY, Maine – The Maine Island Trail Association (MITA) is seeking applicants for two seasonal island caretaker positions for the 2026 boating season, one on Jewell Island and one on Little Chebeague Island. The five-month roles, beginning in May and ending in September, offer a $11,500 living stipend and require a commitment to environmental stewardship and public interaction.

The caretakers will be responsible for maintaining trails, campsites, and other facilities on their respective islands, as well as managing stewardship projects like invasive plant control and marine debris cleanup. They will also serve as a resource for the thousands of visitors who explore Casco Bay’s islands each year, educating them about low-impact recreational practices and the unique ecology of the region.

Jewell Island, a 221-acre island on the outer fringe of Casco Bay, receives over 2,500 visitors annually, drawn to its 2.5 miles of hiking trails, sandy beaches, and remnants of World War II fortifications. Little Chebeague Island, connected to Great Chebeague by a sandbar, is also a popular destination, attracting thousands of boaters and residents. MITA has been actively enhancing Little Chebeague as a public recreational resource since 2010, focusing on trail maintenance and invasive plant management.

According to MITA, the positions require coastal boating experience, excellent communication skills, and the ability to work independently in a remote setting. Applicants must be physically capable of lifting 70 pounds and navigating rugged terrain. A valid driver’s license is also required. Desirable qualifications include experience in education, volunteer coordination, trail maintenance, and wilderness first aid.

Each caretaker will live in a minimally-outfitted cabin on their assigned island and will be provided with an 18-foot motorized aluminum skiff, dock space, a mooring, and a kayak or rowboat, along with necessary maintenance tools. Caretakers are responsible for providing their own food and drinking water. The work schedule will transition throughout the season, beginning with a preparatory phase in May, moving into a five-day-a-week schedule including weekends and holidays from Memorial Day through Labor Day, and concluding with a wrap-up period in September.

MITA stated its commitment to equal employment opportunity, prohibiting discrimination based on race, color, religion, national origin, sex, age, sexual orientation, disability, or other legally protected characteristics.