Executive Retreats
& Peer Advisory Gatherings
At Willowood Washington, we understand the unique challenges facing today’s executive leaders. Our private estate offers an exclusive retreat space where leadership organizations, peer advisory groups, and executive teams can gather, strategize, and lead with intention. Whether you’re part of YPO, EOS, EO, Vistage, or any executive leadership community, you’ll find the space to think boldly, connect deeply, and create lasting impact.
Surrounded by 200+ years of history and 66 acres of natural beauty, Willowood provides the perfect environment for confidential discussions, strategic planning, and meaningful leadership development – all within just 90 minutes from Washington, D.C.
Designed by Leaders, for Leaders
As active members of both YPO (Young President’s Organization) and EOS (Entrepreneurial Operating System), Willowood’s owners have personally experienced the transformative power of peer advisory groups and leadership forums. Drawing from this experience, they’ve thoughtfully designed every aspect of the estate to support the unique needs of executive leadership gatherings.
Whether hosting YPO Forum Retreats, EOS Quaterly Planning Sessions, Vistage CEO Groups, or custom executive team offsites, Willowood provides the ideal setting for confidential discussions, strategic breakthroughs, and leadership development that drives both personal and organizational growth.
Leadership Gatherings with Impact
Create transformative leadership experiences with curated retreats designed to foster deep connections, strategic thinking, and meaningful growth. Our comprehensive approach supports every aspect of executive development, from morning visioning sessions to evening reflection and relationship building.
Below is one example of how you might structure a leadership retreat at Willowood Washington. Our team will work with you to create a fully customized experience that aligns with your organization’s specific methodology, whether you follow EOS principles, YPO learning frameworks, Vistage accountability models, or your own leadership development approach.
MORNING
Refresh & Strategize: Wake to coffee and a chef-prepared breakfast on the patio before hosting a guided meditation session or morning workshop.
MIDDAY
Engage & Collaborate: Break for a gourmet lunch in the Schlosser barn, then participate in a team-building activity such as horseback riding, outdoor challenges, or a cooking class.
AFTERNOON
Inspire & Unwind: Host a brainstorming session under the Oaktree Glen before heading out on a winery tour or enjoying a massage to recharge for the evening.
EVENING
Connect & Celebrate: Gather for an elevated private dining experience, then finish the night with stargazing and fireside conversations to strengthen bonds.
Available for Overnight YPO, EOS, & Corporate Retreats
See what’s available for overnight retreat bookings here, and scroll down for a menu of premium enhancements also available to compliment your stay.
COMPLETE ESTATE PRIVACY
Your leadership team will have exclusive access to the entire 66-acre estate for sensitive strategic discussions, peer advisory sessions, and events that foster meaningful connections. The historic farmhouse, event spaces, and expansive grounds are exclusively yours.
- 2 Nights Included
EXECUTIVE ACCOMMODATIONS
Five luxury king suites with ensuite baths provide comfortable lodging for overnight leadership retreats, with additional on-site capacity available for larger executive groups and forums.
- 2 Guests per Room
STRATEGIC PLANNING SPACES
Multiple indoor and outdoor venues perfect for breakout sessions, group discussions, one-on-one coaching conversations, and confidential peer advisory forums.
- 2 Guests per Room
DAILY HOUSEKEEPING
Ensuring a comfortable and seamless experience.
- Professional Service
LEADERSHIP DEVELOPMENT DINING
All meals are crafted on-site by our private chef, with menus designed to support your retreat schedule and accommodate working meals, celebration dinners, and informal networking opportunities.
- Menu Planning With Private Chef
WINE & SPIRITS SELECTION
Unwind after a productive day with a thoughtfully selected assortment of house wines and spirits available for your enjoyment.
- House Wine & Spirts
TEAM BUILDING & RECREATIONAL ACTIVITIES
Choose from various nature-driven and experiential offerings.
- Connection & Collaborating
BEVERAGE STATION & OPEN PANTRY
Keep the energy flowing with all-day access to fresh coffee, tea, soft drinks, and an open pantry stocked with snacks and refreshments.
- Stocked Pantry
Premium Enhancements
Looking for a little more? Customize your overnight corporate retreat at Willowood Washington to match your goals. Below are some of our most popular premium experiences to choose from. Looking for something else? Get in touch with our team, and we’ll help you tailor something totally your own.
Reserve Your Date
Willowood Washington is available exclusively for private buyout. Make a reservation, and we’ll get to work crafting a customized experience tailored to your every desire.
@WILLOWOODWASHINGTON
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