Skipjack Elsworth

Manage our Fleet on the Chesapeake Bay!

Posted: Jul 23, 2026

Historic Fleet Director

Echo Hill Outdoor School

Worton, Maryland

Wages/Pay
$42,000.00 - $55,000.00 / year
Experience Level
Previous experience required
Job Start Date
Aug 02, 2026

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.

Job Description

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.

Program

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.

Responsibilities

Fleet Management & Maintenance

  • 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.

Budget Management and Logistics

  • 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.

Leadership

  • 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.

Qualifications/Experience

  • 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.

Other Requirements

  • 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

Benefits

  • 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


How to Apply

Send resume to fleet@ehos.org, attention Peter Rice, Executive Director.

Contact Info

Echo Hill Outdoor School

Our mission is to provide visiting students and groups with positive experiences in the outdoors that are exciting, interesting and fun. Experiential curriculum areas include: Watershed Ecology of the Chesapeake Bay and its ecosystems, group and individual development on our low and high ropes adventure course, and exploration of history and the human environment in the Chesapeake Bay region.

Location
Maryland
Season
Spring, Summer, and Fall
Staff size
30-35 program staff
Housing
Whether included in the compensation package or provided at a cost, housing is provided for staff.
Housing details
Optional staff housing, not required
Meals
Some meals / discounts
Cell phone service
Some, ask for details
Internet access
Good
About CoolWorks

Since 1995, CoolWorks has connected adventure-seekers with job opportunities in amazing places—from national parks to ski resorts, summer camps to dude ranches. We help people trade screen time for real time—meaningful experiences that spark connection and growth. Your next great adventure is waiting. More About CoolWorks

Need Help?

Check out our Help Center for FAQ's and helpful articles on how to use CoolWorks. For more in-depth information on how to navigate the world of Jobs in Great Places®, whether you're a Job Seeker or an Employer, visit our Resources page.
Scroll Less. Live More.