Signature Event Steward

About Us

The Trustees of Reservations (The Trustees) is Massachusetts' premier conservation and preservation organization, founded in 1891 by a group of visionary volunteers. We preserve properties of exceptional scenic, historic, and ecological value for public use and enjoyment. Our mission is to protect special places for future generations, with over 50,000 acres conserved, including 27,000+ acres on more than 120 reservations open to the public. As a nonprofit, we are supported by visitors, members, volunteers, and donors.

Salary/Hourly Rate: $17-$19
Hours per week: 30-40, varies based on need
Location: Naumkeag, Stockbridge, MA
Duration: September 1, 2026 - January 3, 2027 (extensions may apply)

About the Role

Join us as a Signature Events Steward to support the setup, operation, and breakdown of two iconic events: the Incredible Naumkeag Pumpkin Show and Winterlights. This seasonal, onsite role reports to the Property Director and Public Programs Coordinator and involves two distinct shift types: event setup (Mon-Fri, 8am-4pm) and run-of-show (Wed-Sun, 3pm-9pm). Applicants must be available for both shift types.

• Pumpkin Show setup: September 1st - 30th
• Pumpkin Show run-of-show: October 1st - 31st (with optional daytime shifts for Winterlights setup)
• Winterlights setup: November 1st - 27th
• Winterlights run-of-show: November 27th - January 3rd
• Winterlights breakdown: January 3rd onward

Responsibilities

• Assist with event setup, including:
  • Carving and designing pumpkins (real and reusable foam)
  • Installing and hanging lights and seasonal displays
  • Moving hay bales, corn stalks, large pumpkins, gourds, and other materials
  • Decorating event spaces and completing other setup tasks
• Assist with event breakdown and safe storage of decorations/equipment at season’s end.
• Provide exceptional guest service during events by:
  • Greeting and welcoming guests upon arrival
  • Checking in guests and scanning tickets
  • Staffing the historic house and answering visitor questions
  • Operating concessions and assisting with food/beverage purchases
  • Serving as a floater to support smooth event operations
  • Assisting with wayfinding, crowd management, and maintaining a safe, enjoyable experience
  • Responding to guest questions with a friendly, professional attitude

Requirements

• Ability to work in all weather conditions (rain, snow, etc.)
• Comfortable being on your feet for extended periods and walking up/down hills/stairs
• Ability to push/pull/lift heavy objects (20+ pounds) and work on a ladder
• Excellent "people skills" to collaborate with employees, volunteers, and the public
• Proven ability to work independently and as part of a team
• Current authorization to work in the U.S. by the first day of employment
• Valid driver’s license and satisfactory driving record per The Trustees' policy
• Satisfactory criminal background (CORI) check

Don’t meet every requirement? We encourage you to apply if you’re passionate about the role—historically marginalized groups are less likely to apply unless they meet all criteria, and we’re committed to building a diverse team.

Benefits

• Sick Time: 40 hours of paid sick time upfront (seasonal); prorated by length of service (limited-term)
• Reciprocity: Free/discounted admission to 50+ nearby museums and cultural institutions
• Discounts: Free entry to all Trustees properties, discounted event tickets, and merchandise
• Limited-Term Benefits:
  • Vacation time (prorated by length of service)
  • 12 set holidays + 3 floating holidays
  • Health insurance via Blue Cross Blue Shield (BCBS), including fitness reimbursement and wellness rewards
  • Short-term and long-term disability insurance
  • Massachusetts Paid Family Medical Leave
  • Life insurance
  • Employee Assistance Program (confidential mental health, counseling, and financial advice)