Director of Trail Development - Capital Trail Extension

Job Title: Director of Trail Development - Capital Trail Extension

Location: Hybrid (Williamsburg, VA and Richmond, VA)

Reports To: Executive Director

Employment Type: Full-Time, Exempt

Position Summary

The Virginia Capital Trail Foundation (VCTF) is seeking a strategic and relationship-driven Director of Trail Development to lead the effort to extend the Capital Trail from James City County through the City of Williamsburg. This public-facing role will serve as the primary liaison for the extension, responsible for building support, coordinating stakeholders, advocating for the project, and helping to secure necessary funding.

Key Responsibilities

Planning & Coordination

• Lead the overall effort to extend the Capital Trail from planning through implementation.
• Develop and manage a comprehensive work plan with clear milestones, timelines, and deliverables.
• Coordinate with local governments and other partners to align technical and design planning with project goals.
• Monitor project progress and provide regular updates to VCTF leadership and stakeholders.
• Attend and/or lead public meetings related to trail planning.

Stakeholder Engagement

• Serve as the primary liaison and spokesperson for the Capital Trail Extension.
• Build and maintain strong relationships with local and state officials, public agencies, tourism partners, landowners, and community leaders.
• Facilitate a multi-jurisdictional working group and internal advisory committee to ensure alignment and accountability.
• Represent the project at public meetings, community events, and in the media.

Advocacy & Public Outreach

• Develop and implement a public engagement plan to inform and involve residents, businesses, and community organizations.
• Create opportunities for public input and ensure the project reflects local needs and values, as needed.
• Collaborate with VCTF staff to produce clear, compelling messaging and visuals.
• Build grassroots support through outreach campaigns, events, presentations, and storytelling.

Fundraising & Resource Development

• Support the execution of a comprehensive funding strategy in partnership with the Executive Director.
• Assist in raising private and philanthropic funds to support key project needs such as grant match requirements, trail amenities, and early-phase planning.

Other

• May assist with VCTF events and programs, as needed.
• Performs other duties as assigned by the Executive Director

Qualifications

Education & Experience

• Minimum of 5 years of experience in project management, community development, urban planning, trail development, or related fields - preferably with multi-jurisdictional infrastructure projects.

Skills & Competencies

• Strong understanding of community engagement, trail development, and land use planning.
• Familiarity with trail planning or transportation infrastructure.
• Excellent interpersonal and communication skills, with the ability to build trust with diverse stakeholders.
• Comfortable working with government agencies, civic groups, donors, and the general public.
• Experience with fundraising, grant writing, and infrastructure funding is a plus.

Personal Attributes

• Passion for trails, outdoor recreation, and community connectivity.
• Strong problem-solving skills and attention to detail.
• Flexibility to navigate complex political environments and multi-jurisdictional dynamics.
• Highly self-motivated, organized, and collaborative.

Work Environment

• This is a full-time, hybrid position with an expected in-person presence in both VCTF’s Richmond headquarters and the project area in Williamsburg. The Director of Trail Development will primarily work from Williamsburg (approximately 3 days/week) at an office, with regular travel to Richmond for internal meetings and team collaboration.
• Occasional evening and weekend commitments for community meetings or events.