The Trustees of Reservations

200 High St.
Boston, MA 02110


Date Posted:
April 05, 2021

Western Massachusetts



Trails Team Leader - Western, MA


The Opportunity.

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.

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.


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.

About The Trustees

The Trustees is one of Massachusetts’ largest non-profits and the nation’s first conservation and preservation organization. Today, the places we care about are going fast, and the forces undermining them, including climate change, are moving faster.?Our passion is to protect and share with everyone the irreplaceable natural and cultural treasures under our care.?We are funded and supported entirely by our visitors, supporters, volunteers, and more than 60,000 member households.


The Trustees has been featured in the Top 100 Women-Led Organizations in Massachusetts for six consecutive years.


In addition to being an Equal Opportunity Employer, The Trustees aims to create a thriving, inclusive workplace that values each member of its team. We aspire to reflect and effectively serve the residents and communities of Massachusetts who are at the core of our mission.


The Trustees is a signer of the Boston Women’s Workforce Council and a Member of the Boston College Center for Work and Family.

We kindly request that you do not call to inquire about the status of your application. Those candidates chosen for interviews will be contacted.

How To Apply:
Please apply online via The Trustees website linked here.
Apply by:
May 31, 2021
$40,000 - $60,000
About this Organization:
The Trustees of Reservations is one of Massachusetts’ largest non-profits and the nation’s first conservation and preservation organization. We preserve and protect places of natural, scenic and historic beauty and hold these “reservations” in “trust” for public use and enjoyment. Our passion is to improve the quality of life in the Commonwealth, using our properties and their many programs as a powerful and compelling platform to engage more residents and visitors in our mission-driven work. We believe in protecting the irreplaceable forever, for everyone.  Today, we care for 117 special reservations -- from beaches to farms, gardens and historic sites – within minutes of every resident. Funded and supported entirely by our nearly 2 million visitors and supporters, and more than 60,000 member households, we invite you to find your place.