Written by: Madison Filson
In addition to providing safe and affordable housing, Windy Hill’s Resident Services team works every day to foster meaningful experiences, encourage community engagement, and support the overall well-being of our residents. This December, the holiday season brought with it a special opportunity to strengthen those connections through festive gatherings and cherished traditions. Our residents, staff, volunteers, and community partners came together in ways that reminded us of all of what this season is truly about: joy, togetherness, and belonging.
The month began with one of our most beloved traditions, our annual tree decorating at Levis Hill House. Residents gathered with ornaments, lights, and plenty of holiday spirit to transform the community room into a warm and welcoming space. Our wonderful volunteers baked brownies and brought a variety of cookies for residents to enjoy while decorating, adding an extra layer of comfort and togetherness. Many residents shared how meaningful it felt to come together in this tradition, noting how the experience brought back happy memories and made the building feel alive with joy. The shared laughter, stories, music, and holiday treats created an atmosphere that set a beautiful tone for the celebrations that would follow.
This year’s tree decorating held special meaning thanks to the involvement of someone who remains deeply rooted in Windy Hill’s mission, our former Executive Director, Bob Dale. Bob returned to support the community he led for so many years, personally helping secure and deliver the Levis Hill House Christmas tree. His continued dedication exemplifies his longstanding commitment to the residents he has served and supported.
Later in the month, Bob extended his generosity once again by volunteering as the special guest bus driver for the resident trip to the Festival of Lights. His warmth, familiarity, and genuine care brought an extra sense of comfort and excitement to the outing, an embodiment of his belief that, “I am passionate about making a difference in people’s lives and sometimes that can be as simple as doing something that fills them with joy.” Bob’s presence this season reminds us of the lasting impact of leadership grounded in compassion and community.
Another special highlight of December was Windy Hill Foundation’s first-ever participation in Christmas in Middleburg Parade. Staff, Board members, and residents proudly represented Windy Hill as they walked through the center of town during one of the region’s most cherished holiday traditions. The energy was electric, with children waving, families cheering, and participants feeling genuinely seen and celebrated by the wider community. This meaningful moment marked an important milestone in Windy Hill’s growing visibility and connection within Middleburg and is a tradition we hope to continue for years to come. Caylee Kwon, who has been a part of the Windy Hill Foundation community, shared, “It felt really good to be part of the parade, and I especially enjoyed being a part of the float. Handing out candy was one of my favorite parts, and seeing people say they love WHF and that people support us was a big moment that stood out for me. The entire parade was amazing.”
To close the month, residents boarded the bus, once again driven by Bob Dale, for a magical trip to the Festival of Lights in Centreville. The evening was filled with brilliant displays, glowing tunnels, animated scenes, and excitement at every turn. Beyond the beauty of the lights, the outing offered residents a meaningful opportunity to relax, bond with neighbors, and experience the joy of the season together. Many shared that the sense of connection made the evening especially memorable. The ride home was filled with conversation, laughter, and gratitude for a night that will undoubtedly be remembered.
As we reflected on the season, the impact of Windy Hill’s care and generosity was perhaps best captured in the words of one resident: “I just wanted to give you a huge Thank you to you, Michelle, and the whole Windy Hill Foundation team for taking the time to get my children’s gifts and wrapping them. I couldn’t help but peak in one bag and my oldest kids’ shoes are in there. He’s going to be so excited, you have no idea! I am forever grateful for you all. Thank you so so so much.”
Together, these holiday festivities embody the spirit of Windy Hill Foundation’s mission. By nurturing traditions, encouraging shared experiences, and strengthening community ties, we can create moments that bring joy, build connections, and remind residents that they are part of a caring and supportive community. This December was a beautiful reflection of what can happen when staff, partners, volunteers, and residents come together with intention and heart.
As we reflect on these celebrations, we offer our heartfelt thanks to everyone who made this month so special; their continued dedication to Windy Hill remains a treasured gift. The community’s generosity and involvement this season has helped create holiday magic that residents will carry with them long after the decorations come down.
