The Trustees of Reservations

200 High St.
Boston, MA 02110

Date Posted:
June 28, 2019

Western Massachusetts



Trail Steward - Windsor, MA (seasonal, part-time)


Focusing primarily on sustainable recreational trail reconstruction and maintenance projects, the Trail Steward works as part of a statewide team, focused in Western MA, to protect, restore, and enhance our trail resources and systems, the environment, and visitor experience through high quality trail work.

The Trail Steward is knowledgeable on the use and maintenance of tools, and basic trail work skills.

Essential Functions

  • 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), and new trail construction.
  • Performs routine monitoring and maintenance of trail systems, including updating wayfinding signage and blazing, removal of encroaching vegetation, clearing trails and entrances of hazard or downed trees, cleaning drainages, and checking trail conditions.
  • Assists with baseline standards assessments of trails and entrances.
  • Works within 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 the Trails Team, with other staff across the organization, and with volunteers.
  • Uses and maintains vehicles, tools and equipment to the highest safety standards.
  • Other duties as assigned with or without accommodation
  • Minimum of one year or season of professional experience associated with the responsibilities of the position

  • Proven ability to work independently or collaboratively as a team member.

  • Proven ability to complete assigned projects and tasks, meet deadlines and manage multiple tasks.

  • Basic knowledge of trail problems and work, and tool use to address them.

  • UTV operation, and power tool use training, preferred.

  • Wilderness First Aid certification, preferred.

  • Commitment to natural resource protection.

  • Strong commitment to the mission of The Trustees.


  • Must be able to carry up to 50 pounds of gear and tools.

  • Ability and willingness to travel across the state to work in remote locations.

  • Valid driver’s license required for driving Trustees’ vehicles, must pass a driving background check per Trustees’ Driving Policy.

  • Other licenses may be required to perform certain functions of the position.

  • CORI check required

  • Experience working with volunteer groups preferred.

Working Conditions

  • Variable outdoor weather conditions.

  • Ability to lift 50 pounds of gear and tools required.

Benefits and Salary

This is a seasonal, non-exempt, hourly paid position. This position is based in Windsor, MA.

About The Trustees:

The Trustees is an organization with a fascinating past and an exciting future. Our places are open to all and we thrive by involving as many people as possible in what we do. Founded in 1891, by a group of visionary volunteers, we preserve, for public use and enjoyment, properties of exceptional scenic, historic, and ecological value in Massachusetts and work to protect special places across the state. We have helped protect more than 50,000 acres, including 26,000+ acres on 117 reservations that are all open to the public. We are a nonprofit conservation organization funded and supported entirely by our visitors, supporters, volunteers, and more than 60,000 member households.

Our seasonal staff plays an integral role in ensuring that our visitors enjoy our extraordinary places. With the change to warmer temperatures, we experience an influx of visitors of all ages and backgrounds who want to explore and be inspired by our properties. Sandy beaches, wooded trails, cultural gardens, historic homes, community supported agriculture—there are many ways for visitors to discover and explore The Trustees, and just as many opportunities for seasonal employees to make each visitor’s experience special.

The Trustees offers competitive compensation and the opportunity to be part of a dedicated team across the Commonwealth who love the outdoors, who love the distinctive charms of New England, and who believe in celebrating and protecting our special places, for everyone, forever.

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

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 via The Trustees' website, linked here
Apply by:
July 20, 2019
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.