Signature Event Steward - The Trustees - Stockbridge

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, https://thetrustees.org.

Posting Information:

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 attitude

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. 

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 people@thetrustees.org