Does your child dream of calling the shots? Now’s their chance! 

The winner of this exclusive experience will join Krista as Head of School for a Day!

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!

Market Value: PRICELESS

Unsurprisingly, Tremont science teacher Kate Charles is multi-talented and great at combining her interests in unexpected and illuminating ways, such as her watercolor paintings.

In The Age of the Ammonites, Kate draws from genetic and fossil evidence to create a beautiful and inspired representation of the predatory marine mollusk that became extinct approximately 66 million years ago. 

This artistic rendering draws inspiration from fossils Kate has collected, and she notes similarities between the ammonite and the vampire squid found throughout temperate and tropical oceans.

11” x 14” watercolor, matted and framed 

Market Value: $175

Do you have plans for Columbus Day weekend, 2026? No? 

Well, you do now if you win this item! You’re going to Provincetown, MA!

This exclusive weekend getaway donated by the French-Daniele family, current Tremont parents, is right in the middle of Provincetown. Steps from some of the best restaurants on the Cape, plus lots of local activities such as: bike riding through the beach dunes, whale watch or harbor cruises, art galleries, kayaking, hiking the trails around Cape Cod National Seashore, and much, much more.

The house offers a fully stocked kitchen, sleeping for 8, in four bedrooms (1 king, 2 queens and a double), plus a single pull-out couch, and three full baths. Large backyard with dining area and seating area with fire table. On top of all that, there is also parking for 3 to 4 cars!

It will be a Columbus Day to remember for the winner of this vacation rental!

Market Value: $4500

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!

"Sueños de Color" (dreams of color) explores dreams as felt experiences rather than fixed narratives, where layers of color drift and collide like fleeting images that never fully settle. Color becomes the primary language—bold passages pulse with energy while softer transitions create moments of pause and reflection—allowing the composition to resist a single focal point and instead invite wandering. There is a quiet sense of movement throughout, as if something is always unfolding just beyond reach, capturing the essence of dreams as vivid, fragmented, and deeply personal.

36" x 48", Acrylic on canvas. 

Market Value: $750

Enjoy a private chef–curated taco in-home dinner experience for 6 to 8 guests that celebrates bold flavor, craftsmanship, and fresh, seasonal ingredients with Chef Brian Miller of Miller PCS, Personal Chef Services!

Each course is built around hand-pressed, fresh masa tortillas, layered with thoughtfully prepared meats and vibrant vegetables. From creative proteins to bright, herb-forward accompaniments, every bite is designed to elevate the humble taco into a multi-course culinary journey. 

The evening is complemented by a tequila paired with each course, selected to complement your meal and enhance the depth, spice, and character of the menu. 

An immersive, elevated dining experience from start to finish. 

Market Value: $1200

Set sail from beautiful Mystic, Connecticut for a 4 hour private sailing adventure designed just for you and 3 friends with Julie and Dave Purrington, Tremont Alumni parents (and Julie is a board trustee). 

Whether you’re in the mood for a relaxed coastal cruise, an exhilarating sail with the wind in your hair, or even a little fishing, your experienced captains will tailor the experience to your interests. Included is a delicious lunch and refreshments customized to your preferences as you take in the stunning shoreline and classic New England maritime charm. Depending on your chosen route, you might sail past the famous Watch Hill shoreline (home to Taylor Swift’s seaside estate) or drop anchor near Fisher’s Island for a refreshing swim. 

Perfect for couples, families, or a small group of friends looking for a memorable day on the water.

Market Value: $750.

Deb Abrahams-Dematte isn’t just the Director of Development at Tremont, she’s also an avid muffin maker and whole foods cook, known to her friends as the Kitchen Witch.

This package entitles the winner to weekly delivery of 1 dozen muffins, for four weeks in a row! (Pick up at Tremont School on dates to be determined with the winner.)

Taking your food restrictions and preferences into account (vegan, gluten free, savory, sweet, fruity, etc.), she will create a month of muffin experiences to tickle your taste buds and fill your stomach.

Market Value: $200

Roll the dice, determine your fate. Heed the warning: if Eric smiles, it is already too late. 

Join up to 5 of your friends in a private, custom, 3-4 hour Dungeons & Dragons one shot game led by Dungeon Master extraordinaire and current Tremont parent, Eric Feltz. All levels welcome.

Date and location to be mutually determined.

Market Value: $300

Score big with this ultimate New England Patriots fan experience! 

Enjoy four tickets to a Patriots home game of your choice, complete with a parking pass and exclusive access to the GP Atrium, where you’ll indulge in complimentary food and non-alcoholic drinks. Plus, Super Fan swag package including mini helmet signed by Christian Gonzales, Patriots Foundation mini football, logo hat and official mug.

Game day doesn’t get better than this!

Market Value: $2300

Give your child a summer they’ll never forget at Camp Waziata, for children ages 6-16, in Waterford, Maine— one of the highest-rated camps in Maine and among the Top 50 summer camps in the U.S. 

Set on 130 beautiful acres along a pristine 3.5-mile lake, “Wazi” offers a welcoming, close-knit community where kids are celebrated for exactly who they are — with no cliques and no technology to distract from real connection and fun. Campers can explore 30+ exciting activities, from water skiing and high ropes to theater, sports, and creative arts. Every day brings new friendships, confidence-building challenges, and joyful outdoor adventure.

Winning bidder receives a 4-week session, giving their child the chance to grow, play, and belong in a truly special summer environment. 

(Session dates subject to availability.) 

Market Value: $8,450

Complement any outfit with this collection of artisan-crafted limited edition jewelry. 

Three beautiful pieces: fabulous red crystal earrings with matching necklace; and a handcrafted pink pendant suspended from a necklace of freshwater pearls. 

Market value: $150

Gift certificate for $300 in art of your choice from the Downsize for Diversity program. 

Generous artists across Massachusetts donate original art and sculpture to the Downsize for Diversity program, and all funds raised from the sale of these art pieces support the Boston Bridges Initiative, a 501(c)(3) based in MA, that supports programs such as Friends of METCO, METCO, and similar diversity and inclusion focused organizations. 

View the complete collection of available artwork here: https://bostonbridgesinitiative.org/downsize-for-diversity

or in person at the Schmergel family household, a current Tremont family!

Market Value: $300

Does your kid want to try sleep-away summer camp, but needs more scaffolded social and executive function support from adults? This Camp Akeela and Beyond Akeela item is for YOU!

Winning bidder receives $1000 off the Akeela program of their choice. 

This is a great experience for middle or high school students who are looking to grow in independence over the summer, challenge themselves outside of their comfort zone, and make new friends. Seems just like Tremont School, but summertime in Vermont or Milton.

Beyond Akeela: Socially immersive college readiness summer camp (non-academic) on the campus of Curry College in Milton, MA for ages 16-19.

Camp Akeela: Traditional overnight summer camp set on 400 acres in the picturesque Green Mountains of Vermont for ages 9-17.

Market Value: $1000

Spend a day in Boston, sometimes called "Bean Town" due to its association with the molasses trade and Boston baked beans.  

Explore classic Bean Town favorites with these passes to Institute of Contemporary Art Boston (2 museum passes), Isabella Stewart Museum (4 passes), and to the iconic Swan Boats (4 passes) plus Peabody Essex Museum in Salem (4 passes).

Market Value: $246

Do you know a kid that loves to STEAM it up? Bring your kids (grades K through 10) to explore and create at Einstein's Workshop in Lexington, with all their Science, Technology, Engineering, Art, and Math classes!

Drop in to the workshop and try out some Lego Robotics, play a new boardgame, or give a go at Minecraft or NASA's Kerbal. 

Drop in vouchers for 5 single days and 2 one-month memberships to Einstein’s Workshop. 

Market value: $315

Come hike with Tremont Alumni and Summer Program staffer Ryan Little leading the way! 

You never know what you will get when you head out on the trail with Ryan, but it's always an adventure that includes climbing all the things, unexpected wildlife, and beautiful views. 

Ryan’s mom, Jen (Tremont Alumni parent and Tremont Board Trustee) will work with the winner of this item and plan a custom hike that fits your group's fitness levels, interests, and time limitations. Lunch and snacks will be provided to be enjoyed at a scenic viewpoint along the hike.

Market Value: $120

Enjoy three classes at CFE Fitness (in Burlington, MA) and take home a tote filled with towels, chalk, and bubbles—a playful twist that proves wellness should always include a little joy.

Market Value: $100

Puzzles and escape rooms and high ropes courses will stretch your body as well as your brain, and teamwork makes the dream work if you want to navigate these challenges, so bring your friends.

Passes to Boda Borg ($150 gift card), Level 99 (4 passes), and Treetop Adventures (2 passes)

Market Value: $500

Enjoy a full year of unforgettable visits with a Friends & Family membership to the New England Aquarium. With admission for 4 each day, priority entry, and other member perks, you’ll explore everything from playful penguins to sea turtles again and again. Perfect for easy family outings and spontaneous adventures all year long.

Market Value: $147

Photographer John Scott is offering a 90-minute photography session at an agreed-upon time and location. 

Whether you need professional headshots, a family portrait session, or you missed out on your true calling as a model, John has you covered. Shoot will include 10 fully edited digital prints. Check out johnscott3.com for more examples of his work. 

Market Value: $1000