Trustees of Reservations

Trails Team Leader

Posted: April 06, 2021
Location: Bullitt Reservation - Ashfield, MA
Time Commitment: Full-time

The Trails Team Leader is responsible for identifying and executing trails specific stewardship needs across the region and will coordinate assisting other stewardship staff as scheduled. In addition, the Trails Team Leader will provide site-based leadership for trails projects and maintenance work where multiple staff are present, and this role will serve as a coordinator for capital and special projects as appropriate. This position is also responsible for performing assessments for Trails and Entrances in their region and scoping the associated work orders. This position is primarily field based with some administrative tasks required to identify and plan technical trails initiatives. This role supervises two Trails Specialists, reports to the Associate Field Director, and works in tandem and in collaboration with other regionally based stewardship positions.

Job Responsibilites

In This Role You Will:

  • Identify primary Trails needs using the baseline standards assessment process and work order information.
  • Oversee and perform Trails and Entrance assessments and work order development.
  • Delivers on key trail and entrance project objectives within Annual Work Plans.
  • Communicate Trails priorities for scheduling maintenance and projects-based work on a weekly and monthly basis.
  • Facilitate contractor access and perform day to day oversight associated with capital and special project trails initiatives
  • Lead group workdays associated with trails projects

Along with Trails Specialists:

  • Performs both basic and advanced trail work to a high standard of quality.
  • Performs heavy reconstructive trail work including, but not limited to: trail relocations, tread hardening, culvert installation, rock construction (waterbars and staircases), timber structures (bog bridges and waterbars), bridge construction, and new trail construction.
  • Performs routine monitoring of trail systems and responds to work requests to clear blowdowns, clean drainages, and check trail conditions.
  • Uses appropriate techniques and BMPs related to trail design, layout, building, maintenance, restoration, and preservation for sustainability and desired visitor experience.
  • Works collaboratively as part of a team and with other staff across the organization.
  • Uses and maintains vehicles, machinery, tools and equipment to the highest safety standards.

Required Qualifications

Minimum Requirements.

Education and Experience:

  • Associate degree in Horticulture, Park Management, Forestry, ecology, or another natural resource field or equivalent experience
  • 3 years of related experience
  • 3 years of supervisory experience


  • Strong tactical skills and the ability to lead a crew effectively and efficiently.
  • Technical expertise in trails and best practices associated with this resource.
  • Proven ability to complete, manage, and report on assigned projects and tasks, meet deadlines and manage multiple tasks.
  • Familiarity with Trustees based Trails guidelines, policies, and BMPs
  • Strong communications skills and the ability to effectively share ideas and priorities


  • Valid driver’s license required for driving Trustees’ vehicles; satisfactory driving record check
  • A satisfactory criminal background check (CORI)
  • Flexibility to work nights and weekends may be required

Working Conditions:

  • Variable outdoor weather and physical conditions.
  • Ability to lift 40 pounds required.

Application Process

Apply Online