The winner of this exclusive experience will join Krista as Head of School for a Day! Does your child dream of calling the shots? Now’s their chance! Bid on this once-in-a-lifetime opportunity for your student to step into the role of Head of School for a Day — a VIP experience like no other! 🔹 Lead the School: Your child will shadow the Head of School, make important "executive decisions," and experience what it’s like to run the show. 🔹 Special Perks: Enjoy a behind-the-scenes tour, lunch with Krista, and even a personalized “official” announcement. 🔹 Bragging Rights: Their name on the door, a special feature in the school newsletter, and a day filled with unforgettable memories! This is an exclusive experience—so bid early and often, and give your student the chance to be in charge for a day! Approximate Value: PRICELESS

Did you know that Tremont's Language Specialist and Cultural Coordinator Ed Rocha is also a professional artist when he's not working at Tremont School? It's true! He has generously donated his painting titled Blue Depth to our silent auction! Blue Depth is a 30x40 inch acrylic on canvas. Approximate Value: $250

Tremont student artist Zavier Hillis will work with you to bring your custom denim design imagination to life, just as he did for our HOS Krista! You supply your favorite pair of jeans or other denim item, share your ideas, and Zavier will create sartorial magic (and a gorgeous custom painted design) just for you! Approximate Value: priceless

Come hit the links with Tremont’s very own Rodney Dangerfield! Get ready to channel your inner Happy Gilmore with this incredible silent auction prize—because nothing says “charity” like a few questionable swings and a whole lot of mulligans! Three guests will enjoy a round of golf with parent Dane Callow at Weston Golf Club, where the fairways are lush, the greens are fast, and the only thing lower than your score will be your self-esteem after a few bad shots. Whether you're a seasoned pro or just interested in joyriding the golf carts, this is your chance to swing (slice) and sink some putts in style. Bid big—this is a hole-in-one opportunity! Approximate value: $400.

Ready to climb to the top- wherever that top may be? In the gym, in the trees, or on the trail? Then this is the bundle for you! Passes to Treetop Adventures (2 passes), Rock Spot Indoor Rock Gym (2 passes), and a Trustees of the Reservation membership. Total Value: $240

Spend a day in Boston, sometimes called "Bean Town" due to its association with the molasses trade and Boston baked beans. Explore two classic Bean Town favorites with these passes to Institute of Contemporary Art Boston (4 museum passes), and to the iconic Swan Boats (4 passes). Total Value: $58

Tired of all the hustle and bustle of 2025? Leave the fast paced world behind as you slow things down with a day in Old Sturbridge Village, where they show you what life was like before computers and iPhones with this family pass. Total Value: $78

Everyone needs a little bit of luck on the golf course. With this Good Game Golf Gnome, your games at Button Hole golf course will be nothing but Aces. This package includes golf for 4 plus 4 buckets of balls at Button Hole golf, and your new best golfing friend, Good Game Golf Gnome. Total Value: $124

Are you crazy? Do you love heights? How about jumping out of perfectly good airplanes while they are flying? Then this package is for you! This package is for One Skydive Pepperell Skydiving Tandem dive pass. Total Value: $285

Take a personal virtual cooking class with a professional chef in the comfort of your own kitchen! Learn to make a gourmet meal at home with step-by-step coaching from a professional chef! Receive a shopping list and fire away with all your questions in a lively, hour-long interactive virtual class.   Enhance your culinary skills and techniques or discover new ones with top Los Angeles-based chef. Total Value: $655

Columbus Blue Jackets left winger James Van Riemsdyk played for the Boston Bruins for only one season (2023), and we have a signed Bruins puck to prove it. Total Value: $75

With 4 tickets to selected North Shore Music Theatre performances, you and 3 friends can attend the children's musical of your choice: How I Became a Pirate (April 12-13) Beetlejuice Jr (April 12-13) Finding Nemo (July 24-25) Footloose Youth Edition (August 22) Total Value: $100

Christopher Cross sang it best. If sailing takes you away, or you want to learn how, then this Community Boating membership for the summer of 2025 is for you. Total Value: $375

This Italian Cheese Tasting Includes: 5 types of artisanal Italian cheese shipped to your home. Descriptive notes for each. Balsamic vinegar, assorted jams, Chianti wine jelly. Total Value: $485

The town of Lincoln has wonderful surprises in store for you. This package has a gift basket with 3 Codman Community Farms t-shirts, uncured meat sticks (snacks), dozen eggs and $25 gift card to Codman Farms Store, plus a $50 gift certificate to The Twisted Tree Cafe located in the famous deCordova Museum and Sculpture Park. Total Value: $155

Live the fairy tales of your dreams in the magic land of the family-friendly rides and attractions that parents and children can enjoy together with these passes to Storyland in New Hampshire (admission for 2). Total Value: $120

Scrub scrub scrub all the road salt, bugs, and dirt off your car. Your car is an investment. When it looks good, you look good. Keep that “new car” look with a visit to ScrubaDub Car Wash with this 5 pack of Scrub A Dub car washes. Total Value: $44

We have three peaks on our logo, so ski at three mountains! With passes to Bromley, Pats Peak, and Ragged Mountain you and a friend can turn that logo into a 3-D experience of snow, speed, and fun! Total Value: $438

Puzzles, escape rooms, and Laser tag will stretch your body as well as your brain. Make sure to take your friends with you with these passes to Boda Borg (4 passes), Xtreme Craze (for up to 5 people), and Level 99 (2 four hour passes), teamwork makes the dreamwork if you want to solve these games. Total Value: $500

Escape to the ocean and enjoy 2 nights at the Bayside Resort Hotel on Cape Cod. This property overlooks Lewis Bay, features 2 swimming pools and a poolside cabana bar, and both the beach and the ferry to Nantucket are within a 1.9 mi radius of the property. Total Value: $350