A Sanctuary for Leadership: Executive Retreats at Willowood Washington
September 22, 2025
Discover Willowood Washington, a private estate near DC for executive retreats, YPO gatherings, and board meetings with true privacy.
There are few places left where the noise of everyday business truly falls away. Where vision is sharpened, and the kind of conversations that shape tomorrow can unfold without distraction. Willowood Washington was created to be one of those rare sanctuaries.
Just ninety minutes from Washington, D.C., our 200-year-old estate offers more than a setting—it offers a shift in perspective. For executive teams, board retreats, peer advisory groups like YPO and EOS, and entrepreneurial circles of every kind, Willowood provides the space and seclusion to step away from the constant demands of modern leadership. Here, time slows. Priorities come into focus. And clarity becomes possible.
A Private Retreat
At the heart of the estate, restored gathering spaces invite both productivity and pause. Morning sessions flow naturally in the heritage library, where original woodwork and thoughtful design create an atmosphere equal parts inspiring and grounding. Afternoons might be spent walking the private woodland trails or taking in the stillness of the meadow crests, where ideas often take unexpected shape. By evening, conversations continue by the fire or under a sky unspoiled by city light—a reminder that sometimes the most important breakthroughs come not in the boardroom, but in moments of genuine connection.
Deeper Connections
Every detail at Willowood reflects an understanding of what leaders need most: privacy, comfort, and inspiration. With five heritage suites in the farmhouse and optional enhancements ranging from chef-driven culinary experiences to wellness offerings like guided meditation and yoga, each retreat is designed with both focus and renewal in mind. Groups find themselves not simply meeting, but transforming—returning to their organizations with renewed clarity, stronger bonds, and actionable vision.
Designed for Connection
In a world where stepping away can feel impossible, Willowood exists to prove that stepping away is often the most powerful step forward.
An Invitation for the Season
The doors are open, the fires are lit, and the countryside awaits. Willowood is premiering this fall, and select bookings are available for the Holiday season.
About Willowood
Willowood Washington is a historic 66-acre estate in Boonsboro, Maryland, offering luxury accommodations and event spaces for weddings, retreats, and gatherings near Washington, DC.