Signature Event Steward

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, www.thetrustees.org. 

Posting Information: 

Salary/Hourly Rate: $17-$19 

Hours per week: 30-40/week, varies based on need   

Job Classification: Seasonal or Limited-term 

Job Type: Onsite, schedule does change throughout the duration of the season  

Duration: September 1, 2026 – January 3, 2027 (extensions may apply) 

Location: Naumkeag, Stockbridge, MA   

What You’ll Do: 

Your Impact: 

Are you passionate about creating unforgettable experiences and bringing joy to thousands of visitors? Join us this fall and winter as a Signature Events Steward, working alongside our Engagement and Stewardship teams to bring to life two of our most magical events: the Incredible Naumkeag Pumpkin Show and Winterlights.  

The Role: 

The Signature Events Steward reports to the Property Director and Public Programs Coordinator to support the setup, operation, and breakdown of Pumpkin Show and Winterlights. Shifts are broken up into two different roles with differing hours, set up and run of show. Set up hours will be Mon-Fri 8am-4pm while run of show hours will be Wed-Sun, 3pm-9pm. Applicants must be willing to work both event set up and run of show hours. 

Pumpkin Show set up: Sept 1st - 30th  
Pumpkin Show run of show: Oct 1st - 31st (with options to add a daytime shift doing Winterlights set up) 
Winterlights set up: Nov 1st - Nov 27th 
Winterlights run of show: Nov 27th - Jan 3rd  
Winterlights break down: Jan 3rd - on 

Specifically, you'll: 

Assist with event setup, including but not limited to: 

• Carving and designing pumpkins (both real and reusable foam pumpkins) 

• Installing and hanging lights and other seasonal displays 

• Moving hay bales, corn stalks, large pumpkins, gourds, and other event materials 

• Decorating event spaces and completing a variety of other setup tasks 

• Assisting with event breakdown and the safe storage of decorations and equipment at the end of the season 

Provide exceptional guest service during event operations by serving in a variety of roles, including: 

• Greeting and welcoming guests upon arrival 

• Checking in guests and scanning tickets 

• Staffing the historic house and answering visitor questions 

• Operating concessions and assisting guests with food and beverage purchases 

• Serving as a floater, providing support wherever needed to ensure smooth event operations 

• Assisting with wayfinding, crowd management, and maintaining a safe, enjoyable experience for all visitors 

• Responding to guest questions and representing The Trustees with a friendly, professional attitudeThis is a seasonal, nonexempt position reporting directly to Property Director and Public Programs Coordinator.  

This is a seasonal or limited-term, non-exempt (30-40 hours per week) position reporting directly to the Berkshires and Western Hills Property Director and Public Programs Coordinator. 

What You’ll Need: 

Skills and Experience: 

• Ability to work in all weather conditions (rain, snow etc.)  
• Be on your feet for hours at a time  
• Frequently walk up and down hills/stairs  
• Push/pull and lift heavy objects  
• Must be comfortable working on a ladder  
• Be able to lift 20+ pounds  
• Excellent “people skills” to work cooperatively and harmoniously with fellow employees, volunteers, and the public.  
• Proven ability to work independently and collaborate as a team member.  

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.

• A satisfactory criminal background (CORI) check. 

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 [email protected] 

Your Benefits (Seasonal) 

• Sick Time: 40 hours of paid sick time upfront. 

• 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.  

Your Benefits (Limited Term) 

• Sick time: Provided, prorated by length of service

• Vacation time: Provided, prorated by length of service

• Holiday time: 12 set 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  

• 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: Employees have access to free and discounted admission and membership to more than 50 nearby museums and cultural institutions.  

• Discounts: Enjoy free entry to all Trustees properties, discount event tickets, and discounted merchandise at our stores and on stays at our inns.  

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 [email protected].