Winterlights Production Crew, Visitor Services

The Trustees of Reservations (The Trustees), founded in 1891, is the nation's premier conservation and preservation organization. We preserve and share properties of exceptional scenic, historic, and ecological value across Massachusetts, ensuring they remain open to the public. As a nonprofit, we rely on visitors, supporters, volunteers, and our 100,000 Member households to protect over 50,000 acres, including 27,000+ acres on more than 120 reservations.

About the role

Join our Winterlights Production Crew at the Eleanor Cabot Bradley Estate and help create a magical holiday experience for over 20,000 guests! This seasonal role is perfect for those who love the holidays, enjoy working with people, and want to be part of a festive, unique event. You’ll work in a team-oriented environment, assisting with guest services, concessions, and event operations in one of Massachusetts’ most enchanting settings.

Responsibilities

• Serve as the welcoming face of Winterlights: greet guests, check tickets, and ensure a smooth entry process.
• Operate the gift shop and concessions, preparing and ringing up hot cocoa, treats, and holiday merchandise using point-of-sale systems like Toast.
• Assist with event setup, including hanging lights, prepping supplies, and maintaining a tidy, safe property before guests arrive.
• Support wayfinding, cleanliness, and overall guest experience throughout the event.
• Troubleshoot minor issues and collaborate with the team to keep operations running smoothly.
• Participate in post-event takedown and storage (opportunities available through mid-January).

Requirements

• A friendly, outgoing attitude and passion for working with people.
• Customer service or food/beverage experience (e.g., retail, concessions, barista roles).
• Familiarity with point-of-sale systems (training provided if needed).
• Comfort working outdoors in chilly temperatures and standing for long shifts.
• Ability to lift up to 30 lbs and assist with light setup/cleanup tasks.
• Flexibility and a team-oriented mindset—Winterlights is a collaborative effort!
• Availability evenings and weekends from November 27 to January 2 (closed December 24–25; open December 21–22, 28–29, and January 1).

Schedule

Wednesday–Sunday, 3:00 PM – 9:00 PM (variable hours, up to 40 hours per week).

Pay

$16 – $18 per hour.

Benefits

• 40 hours of paid sick time upfront.
• Free and discounted admission to over 50 nearby museums and cultural institutions for staff, volunteers, and interns.
• Free entry to all Trustees properties, discounted event tickets, and merchandise discounts at our stores and inns.