Gathering in Style: Holiday Retreats at Willowood Washington
September 5, 2025
PLAN YOUR HOLIDAY GATHERING AT WILLOWOOD WASHINGTON, A HISTORIC ESTATE NEAR D.C. WITH TIMELESS CHARM & MODERN ELEGANCE.
There’s something about the holidays that calls us back to the table. As the year winds down, we crave not only celebration but reflection — a chance to pause, connect, and step into the season with intention. At Willowood Washington, this spirit of gathering finds its perfect setting.
Set among 66 rolling acres in Maryland’s countryside, Willowood is both historic and timeless. Its story stretches back to the 1850s, yet today it offers a fresh vision of hospitality: intimate, elevated, and designed to make every moment feel meaningful. The estate is now welcoming groups for holiday retreats and winter gatherings in 2025, and the possibilities are as inspiring as the season itself.
A Retreat for Leaders & Visionaries
For companies, the close of the year is often a time for clarity. Strategic planning sessions, financial reviews, and board retreats require focus — and Willowood was designed to provide exactly that. With its serene landscape and thoughtfully restored interiors, the estate offers an environment where ideas can breathe and conversations unfold without distraction. Evenings transition naturally from fireside discussions to elegant seasonal dining, creating a rhythm of both productivity and renewal.
Celebrations That Feel Like Home
Beyond the corporate calendar, Willowood is also a place for joy. Families, friends, and social circles can gather for weekends that combine the ease of a private home with the polish of a destination venue. Picture a long winter’s table beneath twinkling lights in the barn, laughter echoing in the great hall, or quiet mornings spent walking the grounds. Every space has been restored with intention, balancing heritage with modern comfort, so celebrations feel both festive and effortless.
Designed for Connection
The beauty of Willowood lies not only in its architecture, but in the experience it makes possible. Curated enhancements — from wellness sessions and outdoor excursions to bespoke culinary menus — can be woven into each gathering, ensuring no two are alike. Guests can stay overnight in beautifully appointed accommodations, turning a single evening into a multi-day retreat.
An Invitation for the Season
Willowood is more than a venue. It is a place to pause, to plan, to celebrate, and to savor the richness of the season. Whether you are envisioning a corporate strategy retreat or a holiday gathering with loved ones, the estate offers a canvas upon which memorable experiences are created.
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.