Trails Specialist

Who We Are: Founded in 1891 by a group of visionary volunteers, The Trustees of Reservations (The Trustees) is Massachusetts’ premier conservation and preservation organization. The Trustees’ preserves, for public use and enjoyment, properties of exceptional scenic, historic, and ecological value in Massachusetts. Our properties are open to all, and we thrive by involving as many people as possible in all that we do. We aim to protect special places for future generations to enjoy in perpetuity, and have helped protect more than 50,000 acres, including 27,000+ acres on more than 120 reservations that are open to the public. As a non-profit conservation organization, we are funded and supported entirely by our visitors, supporters, volunteers, and our 100,000 Member households. We encourage you to learn more about The Trustees on our website, Posting Information: Hourly Rate: $21.66 - $27.85  New hires are typically placed within the range of $22.28 - $24.76 per hour Hours per week: 40  Job Classification: Full-Time, Nonexempt  Job Location Type: Onsite  Location: Based out of Dover, MA, this role requires daily travel to other properties in the MetroWest region (Dover, Medfield, Millis, Sherborn, Needham, Uxbridge, Southborough, Burlington, Harvard, Shirley) using a Trustees provided vehicle.   What You’ll Do: Your Impact:  The Trails Specialist works as part of a regional team to protect, restore, and enhance our trail resources and systems, the environment, and visitor experience through high quality trail work. Reporting to the Regional Stewardship Manager, this person is primarily field-based, working both independently and collaboratively with MetroWest stewardship staff and volunteers and occasionally with trail specialists in other regions.  The Role:  Specifically, you’ll:  Demonstrate true dedication to the preservation and restoration of trails, a strong commitment to natural resource protection and alignment with the mission of the Trustees.  Perform both basic and advanced trail work to a high standard of quality, including: heavy reconstructive trail work such as trail relocations, tread hardening, culvert and rolling grade dip installation, rock construction (ex: stairs and retaining walls), native and dimensional timber structures (ex: bog bridges, cribbed stairs, and bridge construction), clearing storm damage, and new trail layout and construction.  Use industry standard techniques and BMPs related to all aspects of trails and entrance design, layout, construction, signage/wayfinding, maintenance, restoration, and preservation for sustainability and optimal visitor experience.  Knowledgeably monitor and maintain entrances and trails in all weather and seasons using standard field and shop tools, both hand and machine powered.  Supervise, train, and lead volunteers and seasonal staff and assist in supervising contractors on trail and entrance projects.  Assess future project work needs and assist in designing solutions for trails and entrances.  Use and maintain vehicles, machinery, tools, and equipment to the highest safety standards.  Perform other stewardship tasks as needed.  This is a full-time, nonexempt position working 40 hours per week reporting directly to the Regional Stewardship Manager.  Requirements What You’ll Need: Skills and Experience: The ideal candidate will have 2 or more years in a similar position/environment, as well as:  Ability to quickly assess trail conditions, spot problems, and identify solutions.  Experience using hand-held power tools (ex: chainsaw, drill, brushcutter).  Basic computer skills in Office365, and an ability to learn and use trustees software. systems and mobile technology.  MA Hoisting 2A License or ability to acquire upon hiring.  Experience and/or training with UTV operation, trailer transport, and light machinery a plus (ex: tractor, mini-excavator, skidsteer).  Associate’s degree in natural resources or related field, preferred.  Wilderness First Aid certification, preferred.  Experience working with volunteers a plus.  Eligibility Criteria:  Current authorization to work in the United States – a candidate must have such authorization by his or her first day of employment.  A valid driver’s license, as well as a satisfactory driving record as outlined in The Trustees’ driving policy.   This role will require driving Trustees vehicles over 10k lbs.  A satisfactory criminal background (CORI) check.  Ability to work in all weather conditions and lift 75lbs  Don’t quite have all the skills and experience listed above? We still want to hear from you! Research shows that historically marginalized groups are less likely to apply if they do not meet every single requirement. We are committed to building a diverse team and encourage you to apply even if you are missing some of the skills and experience above.   Questions? Contact our People team at   Benefits Your Benefits:   Sick time: 15 days per year  Vacation time: 20 days per year (prorated)  12 observed holidays, 3 floating  Health insurance: You are eligible to participate in the Trustees health insurance benefit via Blue Cross Blue Shield (BCBS). BCBS also offers additional benefits, such as fitness reimbursement and rewards for healthy habits.   Short-Term and Long-Term Disability Insurance  Massachusetts Paid Family Medical Leave  Life Insurance   401k with 5% match after 1 year of employment  Employee Assistance Program: Free access to a confidential service that helps employees and their communities with personal and work-related issues, such as mental health support, counseling, and financial advice.   Reciprocity: Enjoy access to free and discounted admission and membership to more than 50 nearby museums and cultural institutions for Trustees Staff, Volunteers and Interns.  Discounts: Enjoy free entry to all Trustees properties, discount event tickets, and discounted merchandise at our stores and on stays at our inns.   Day of Wonder: Spend one workday per year to exploring a Trustees property  Day of Service: Spend one workday per year to helping with a project at a Trustees property   Equal Opportunity and Diversity:  The Trustees is a proud equal opportunity employer and does not discriminate against any protected status including, but not limited to, age, race, ethnicity, sex, gender, sexual preferences, nation of origin, religion, or disability status and strongly encourages applications from people of color, persons with varying abilities, women, and LGBTQ+ applicants. We aspire to reflect and effectively serve the residents and communities of Massachusetts, who are at the core of our mission.     The Trustees’ commitment to advancing the organization’s vision for this work may be found here: Diversity, Belonging, Inclusion and Equity.   It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.   We are committed to creating an inclusive and accessible work environment. To request reasonable accommodation during the application or interview process, please contact us at .

Created: 2026-03-18