Historic Fleet Director

Manage and maintain a fleet of historic Chesapeake Bay wooden boats from a 70-acre waterfront campus in beautiful Kent County on Maryland's Eastern Shore. Echo Hill Outdoor School is seeking a hands‑on Fleet Director to care for six wooden vessels that serve more than 6,500 students each year. This full‑time role blends craftsmanship, leadership opportunities, and time on the water while offering country living near historic Chestertown.

Enjoy easy access to sailing, paddling, fishing, and many other outdoor pursuits, with Annapolis, Baltimore, Washington, DC, and Philadelphia all less than a 2‑hour drive away. If you’re looking for meaningful work, maritime tradition, and a lifestyle rooted in the outdoors, this is an opportunity to build a career with purpose. An ideal candidate will have a strong background in wooden boat building or marine systems, or both.

Candidates with significant operational experience (“seatime”) preferred, but a U.S. Coast Guard license is not required for candidates with a strong marine trades background. Position includes weekday meals and a housing option.

Echo Hill’s Historic Fleet Director will lead all activities related to the preservation, maintenance, and operational management of a fleet of historic vessels. The director will ensure each vessel remains in appropriate condition, is safely operated, and is available for all Echo Hill programs. The selected candidate will have a key role in continuing Echo Hill’s effort, begun in 1972, to provide students with an understanding of Chesapeake Bay ecology and the impact of human activity on the estuarine ecosystem.

Echo Hill Outdoor School’s historic wooden boats are the cornerstone of our science and history programs. These Chesapeake Bay craft were used in the Bay’s fisheries for decades. The School maintains them in the tradition of work boats to provide an authentic historical perspective for students studying current Bay issues. Our boats are certified by the USCG as small passenger carrying vessels, and they are operated by Echo Hill staff who are USCG‑licensed captains.

The boats are used for a variety of classes and ventures that allow participants to study and discover first‑hand the wonders of Chesapeake Bay ecology, history, and culture. Echo Hill programs include weekday classes (3 hours) on the historic workboats SPIRIT (1944) and TWILIGHT (1911) as well as multi‑day programs on the buy boat ANNIE D (1957) and the skipjack ELSWORTH (1901).

The wooden skiffs LEWEY and RIC support our multi‑day programs.

• Oversee the upkeep and repair/restoration of historic vessels, ensuring they meet USCG standards and maintain their historical integrity.

• Coordinate regular maintenance schedules for the fleet, while leading in‑house maintenance program and repairs.

• Work with external shipwrights and contractors to complete major projects.

• Appropriately maintain tools and supply inventory.

• Manage the fleet budget, ensuring that expenditures for repairs, operations, and programming are in line with available resources.

• Work with the administrative team to procure supplies and coordinate timely replacement of equipment/components.

• Manage and mentor other Echo Hill staff assigned to boat maintenance duties.

• Work with captains to ensure appropriate operation of vessels.

• Foster a team‑oriented environment focused on safety and professionalism.

• Work with Echo Hill leadership to recruit, hire, and orient new captains.

• Excellent communication, interpersonal, and leadership skills.

• Formal education or significant experience in wooden boat building and/or marine systems.

• Experience in maritime operations, historic preservation, or fleet management.

• USCG license (25 ton) or interest in obtaining a license strongly preferred.

• Experience working with maritime professionals, including captains and tradespeople.

• Interest in environmental education, maritime history, and preservation of historic vessels.

• Current drug‑free screening (will be enrolled in Consortium)

• Criminal background check required

• CPR and First Aid certification required (obtainable after hire)

• Valid driver’s license and insurable driving record

Annual Compensation:
Starting at $42,000-$55,000

• Medical, dental, vision, available via employee contribution

• 403(b) plan available

• Paid vacation, holidays, and personal days annually

• Professional training and development opportunities

• Weekday meals and housing option