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2026 Heads Retreat
Thursday, November 12, 2026, 12:30 AM to Friday, November 13, 2026, 12:00 PM EDT
Category: AISGW Events

     
Thriving in Flux: Building Resilient Schools for the Future

The theme for this year’s Retreat is Thriving in Flux: Building Resilient Schools for the Future. During our time together we will consider how external trends may create both opportunities and challenges and ask strategic questions to help navigate what comes next. We are pleased to welcome keynote speakers Rebecca Winthrop of the Brookings Institute and Amol Tripathi of Focal Point Coaching, along with Grace Lee of Venable LLP. They’ll share insights on the impact of AI on schools and learning, suggest ways to think differently about organizational resilience and stability, and offer an update on pressing legal issues. We’ll also engage in group problem-solving about sticky challenges and connect with each other based on head tenure.

In an effort to be responsive to the feedback AISGW receives each year, we continue to fine-tune the structure and format of the Retreat while retaining features that we know our heads count on during their time in Middleburg. One change this year includes the location of Thursday night’s dinner which will be hosted on the beautiful campus of Foxcroft School. Also, we have brought back our tenure cohorts, with opportunities for early, mid- and late-career heads to gather for conversation during the retreat.

Retreat attendees must make their own overnight hotel reservations at the resort. Click here for instructions on reserving a room under the AISGW reservation block.
Please reserve your room by October 10th.

Although we are no longer offering a one-day registration option, if you find you can only join us for part of the conference, please reach out to Lynn Maloney



CLICK HERE TO REGISTER FOR THE CONFERENCE PROGRAM