Signature Event Steward

Berkshirejobs; Boston (MA); On-site; USD 23,000 - 26,000; Part time

Job summary

The Trustees of Reservations in Massachusetts is seeking a Signature Events Steward to support two signature events: the Incredible Naumkeag Pumpkin Show and Winterlights. This seasonal, non-exempt role works with the Engagement and Stewardship teams to help set up, operate, and break down event spaces under the supervision of the Property Director and Public Programs Coordinator.

Shifts include Pumpkin Show setup Mon-Fri 8am-4pm and run-of-show Wed-Sun 3pm-9pm, with some Winterlights options.

Qualifications

• Seasonal or limited-term, non-exempt (30-40 hours per week) position.

Responsibilities

• Assist with event setup, including carving pumpkins, hanging lights, moving decor, and general setup tasks.
• Assist with event breakdown and storage of decorations and equipment after the season.
• Provide guest service during events: greet, check tickets, staff house, operate concessions, and assist guests.

Skills

Guest service

Event setup

Crowd management

Wayfinding

Team collaboration

Job description

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 Coordinatortosupport the setup, operation, and breakdown ofPumpkin ShowandWinterlights.Shifts arebroken upinto twodifferent roleswithdifferinghours, setupand run of show.Set up hours will be Mon-Fri 8am-4pmwhilerun of showhours will be Wed-Sun, 3pm-9pm. Applicants must be willing to work botheventset up and run of show hours.

Pumpkin Showset up:Sept 1st -30th
Pumpkin Showrun ofshow:Oct 1st - 31st(with options to add a daytime shift doingWinterlightsset 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:

Assistwith 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

• Assistingwith 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 andassistingguests with food and beverage purchases

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

• Assistingwith wayfinding, crowd management, andmaintaininga safe, enjoyable experience for all visitors
• Responding to guest questions andrepresentingThe Trustees with a friendly, professionalattitude

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