Middleburg, Virginia, established in 1787 by Revolutionary War Lieutenant Colonel and Virginia Statesman Levin Powell, has a rich history that dates to its early days as a staging point for weary travelers along the Ashby Gap trading route. Originally called “Chinn’s Crossroads,” Powell chose the name “Middleburg” due to its location midway between Alexandria and Winchester. Over the years, Middleburg has earned a reputation as the “Nation’s Horse and Hunt Capital,” attracting visitors for its foxhunting, steeple chasing, and large estates.
The holiday season in the quaint one-stop-light town of Middleburg, VA, is a time of joy, reflection, and togetherness. Nestled among horse farms, this charming locale transforms into a festive wonderland every year, as its residents gather to celebrate traditions that have been passed down through generations. Christmas in Middleburg is particularly magical, with the morning Hunt Parade featuring hounds, horses, and riders, plus an afternoon community parade, complete with miniature horses, dogs, and firetrucks galore!
One of my favorite holiday traditions is A Place to Be’s Old-Fashioned Holiday Variety Show, where performances highlight clients of music therapy, which can include neurodiverse, disabled, and stroke survivors. This year the event takes place on December 22nd, at Salamander Resort. There is nothing like an ‘A Place to Be’ experience to start your holiday season feeling grateful and connected to your community.
Our family then takes advantage of the proximity with an annual trip to Washington, D.C., for a dose of culture and fine dining. We will either catch A Christmas Story, the latest Star Wars movie, or this year, the Hip Hop Nutcracker! Once back home for Christmas, we enjoy the simple pleasures of family gatherings, fresh air, and long walks. These customs are designed to foster meaningful connections and promote mental wellness.

The Strays Gathering

One of my most cherished traditions in Middleburg is a “strays gathering.” Many versions exist, and often multiple are hosted throughout the season. A heartwarming event brings together core families and their “strays” friends and family members who, for various reasons, find themselves without a place to celebrate the holidays. These gatherings are a testament to the town’s inclusive spirit and commitment to ensuring that nobody feels alone during this special time of year.
The festivities often begin with appetizers by the fire, followed by a grand potluck dinner, where tables are laden with an array of homemade dishes, from savory casseroles to decadent desserts. The air is filled with laughter and the aroma of delicious food as people share their favorite recipes and stories from years past. Board games, storytelling sessions, and watching classic holiday sports are just a few of the activities that bring people closer together, reinforcing the sense of belonging and togetherness. These casual yet deeply meaningful celebrations set the tone for the holiday season, reminding everyone of the importance of community and connection.
Friends, too, play a vital role in the holiday celebrations. From impromptu get-togethers to more elaborate parties, these social interactions offer a chance to unwind and have fun. The town’s close-knit community ensures that everyone feels included, with neighbors often dropping by with homemade treats or invitations to join in the festivities. These acts of kindness and generosity epitomize the town’s spirit, making the holiday season a truly magical time.

Embracing Nature: Fresh Air and Long Walks

Back in Middleburg, the holiday season is also an ideal time to reconnect with nature. The town is surrounded by scenic trails and Sky Meadows State Park, perfect for leisurely walks and outdoor adventures. These excursions provide a much-needed respite from the hustle and bustle of daily life, inviting residents to breathe in the crisp winter air and marvel at the beauty of their surroundings.
Another favorite spot to visit is the National Sporting Library and Museum (NSLM). Founded in 1954, the inviting 6-acre campus, world-class research Library, and fine art Museum highlight the rich heritage and tradition of country pursuits. Angling, horsemanship, shooting, steeple chasing, foxhunting, flat racing, polo, coaching, and wildlife are among the subjects one can explore in the institution’s general stacks, rare book holdings, archives, and art collections. The NSLM offers a wide variety of educational programs, exhibitions, and family activities throughout the year. For example, the last Sunday of every month features a Sunday Sketch, which I’ve personally participated in, and I can attest that they’re tolerant of participants of all skill levels!

Resetting Mental Wellness: A Season of Renewal

Amidst the joy and celebration, I remind my family to remain keenly aware of the importance of mental wellness. The holiday traditions they uphold are not just about merriment; they are also about resetting and rejuvenating the mind and spirit. The “strays gathering,” the cultural trip, and the time spent in nature all contribute to a well-rounded approach to mental health.
By fostering a supportive community, engaging in enriching cultural experiences, and embracing the healing power of nature, Middleburg’s holiday traditions offer a holistic way to reset and recharge. This thoughtful approach ensures that the holiday season is not only a time of joy but also a period of reflection and renewal, setting the stage for a positive start to the new year.
In conclusion, holiday traditions can be a beautiful blend of communal joy, cultural enrichment, and natural beauty. They exemplify the town’s commitment to fostering deep connections, celebrating diversity, and promoting mental wellness. As the residents come together to celebrate, they are reminded that the true essence of the holidays lies in the love and support of family and friends, and the simple pleasures that bring us all closer together. ❦

About the Author

Shannon Crocker has over 10 years of experience supporting the Department of Homeland Security. She has recently expanded her work to include the Department of Justice and US Courts, creating optimal synergies. Shannon is passionate about empowering her customers in both mission space and IT, enabling greater success, and helping to solve tough challenges. By facilitating cross-collaboration and leveraging Microsoft’s resources, she has found new ways to impact her customers and help them achieve their goals. With the use of modern technology such as Azure Open AI, machine learning, and cognitive services, Shannon is enabling customers to build real mission solutions in weeks, where it used to take years.

Shannon’s previous experience includes working on dynamic flight controls and navigation systems for UAVs, and working with aviation companies supporting the Army. She has also helped facilitate neuroscience research with observational and behavioral software.

Board Memberships and Affiliations: Shannon is currently a board member of three organizations: the Homeland Security and Defense Business Council (HSDBC), A Place to Be (a music therapy organization), and the Middleburg Tennis Club. She is also affiliated with the Homeland Security Dialogue Forum (HSDF), ACT-IAC, and AFCEA.

Education and Personal Life: Shannon earned a Bachelor of Science in Engineering from the University of Virginia. She is married to Sean and has one son, Brodie, who is 15 years old. They reside in Middleburg, VA. In her spare time, Shannon enjoys hiking, playing tennis, practicing yoga, and traveling.

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