26-27 G2G (1)

2026-27

100 Days of Giving

Participate with Purpose

Program Enhancements Innovating for a Dynamic Future

GIVING

2026–27 Planned Program Enhancements Elevating the Arts

Thanks to the extraordinary generosity of our community, Windward School continues to stand as a leading independent institution — now celebrating more than 50 years of academic excellence and growing stronger every year.

The Windward Fund is at the heart of that momentum. Fueled each year by our 100 Days of Giving campaign, it brings together parents and guardians, alumni, grandparents,

The Innovation and Arts Center will reach bold new heights — literally — with the addition of a state-of-the-art scissor lift, empowering our Performing Arts and Visual Media Arts programs to bring even the most ambitious productions to life. From dynamic stage designs and creative possibility across multiple disciplines.

Reimagining the Learning Environment Every gift — at every level — supports the three pillars that define our philanthropic mission: PROGRAM ENHANCEMENTS — expanding the richness of the student experience FINANCIAL AID — ensuring Windward is accessible to the students who need it most RESEARCH & DEVELOPMENT — equipping our educators with the tools and training to lead To drive Windward forward, we need your support this academic year. Your immediate gift is the catalyst that shapes real student outcomes today, energizes our campus right now, and secures our bold strategic vision for the future.

Now is the moment to make your mark. Join the Windward community for our 100 Days of Giving—and help us ensure that every student walking through our doors this year has the immediate opportunity to truly thrive, lead, and shine!

Our academic classrooms will be transformed with ergonomically designed desks, chairs, and whiteboards that foster collaboration, sharpen instructional clarity, and place student comfort at the heart of every lesson. The Science Department will advance its capacity for rigorous inquiry with a new deep freezer and acid cabinet, while the IDEA Lab gains cutting-edge laptops purpose-built to power CAD design and robotics innovation.

Honoring Legacy, Building Strength The Lewis Jackson Memorial Sports Center will proudly celebrate our storied athletic tradition through a stunning new digital Wall of Champions — a living tribute to the dedication and excellence of those who came before. Our student-athletes will also train at the highest level with new foldable wall racks, Rogue weight plates, dumbbell sets, and workout benches, ensuring every athlete has the tools to compete and excel.

$

Financial Aid

Research & Development

Expanding Opportunities

Investing in Excellence

The success of the Windward Fund directly impacts our ability to expand financial assistance for students within our community. Windward School is proud to provide financial aid to 104 students in the 2026-27 school year, ensuring they have access to essential resources that enrich their educational experience.

This support covers vital expenses such as textbooks, technology, athletic gear, uniforms, trips, participation in the Windward bus program, monthly campus food stipends, global study opportunities, field trips, and school events. By removing financial barriers, we empower students to engage in all that Windward School offers. Financial aid strengthens our diverse community and upholds our mission of providing an inclusive and transformative education.

$

5,195,598

2026-27 Financial Aid Budget $ Allowing

104 Students to receive tuition assistance

Representing

15%

8.59%

of students on Financial Aid

Increase from 2025-26 *As of 7/15/26

Professional Development The 2026–27 academic year set a new standard for Faculty & Staff engagement, with record-breaking attendance at conferences, specialized training, workshops, and certifications. With a dedicated $450,000 budget, the Windward Fund ensures our educators have access to top-tier professional development — keeping them at the forefront of their fields, deepening their commitment to Windward, and directly enhancing the student experience.

Alumni Network Beyond engagement, the Windward Fund actively builds an alumni network that creates real-world value. Through professional networking events and collaborative opportunities, current and past students connect, support one another, and thrive — carrying the Windward spirit into every stage of their lives and careers.

Alumni Engagement The Windward Fund cultivates meaningful connections between our school and its graduates through curated events, reunions, and initiatives designed to keep alumni close to the community that shaped them. These touchpoints strengthen loyalty, celebrate shared history, and remind every alumnus that Windward's impact doesn't end at graduation.

$100,000+

100 Days of Giving

Participate with Purpose