May brings a new burst of color to Middleburg — gardens in bloom and that exciting spring rhythm that makes the whole town feel especially alive. It’s the time of year when familiar traditions return, new ones take root, and every corner of town seems to offer something worth stepping outside for. From equestrian favorites and outdoor concerts to spring markets, local fundraisers, and community gatherings, the month is packed with moments that show why Middleburg shines in every season. Explore what’s ahead and make the most of May in our teeny tiny town!
As always, be sure to visit our full Events Calendar for the latest updates. We are always adding more!
Loudoun Lyric Opera Mahler’s Das Lied von Der Erde
On May 2 at 7 pm, Loudoun Lyric Opera concludes its season with an intimate concert featuring Myanmari‑American tenor Ye Lynn Han and mezzo‑soprano Amanda Zoe Vest, in a program curated with Artistic Director Mark Irchai. The performance centers on Mahler’s Das Lied von der Erde, presented in the composer’s own piano edition, offering a reflective musical journey through the landscapes of life.The event also includes a special collaboration with Loudoun County visual artist Terri Parent. Her acclaimed work Through the Fog will be exhibited in the lobby, enriching the audience’s experience with visual interpretations that echo Mahler’s themes.
Matter of Balance Program at Windy Hill Foundation
The Matter of Balance Program at Windy Hill’s Levis House is designed to help older adults reduce their fear of falling, build confidence, and stay active in daily life. Through guided discussions, gentle exercises, and practical problem‑solving activities, participants learn to recognize and manage fall risks, set realistic goals for increasing movement, and adopt proven fall‑prevention strategies. The program also fosters social connection and support, helping participants build confidence and independence.
The Matter of Balance is an 8-week session program designed to manage the risk of falls and increase activity. This program is free, with a suggested donation of $10 and registration is limited to 12 participants.
To register, please call 540-687-3997 or click the button below to register!
Art in the Burg & America 250 Celebration May 9
Middleburg’s beloved Art in the Burg returns this spring with an expanded celebration in honor of America’s 250 Celebration of American Culture & Arts. This annual festival transforms South Madison and Federal Streets into an open‑air gallery, showcasing the creativity and craftsmanship of local and regional artists. Visitors can explore an eclectic mix of paintings, pottery, jewelry, sculpture, photography, woodworking, leather goods, candles, soaps, and more—each piece reflecting the rich artistic spirit of our community.
Throughout the day, enjoy live music and artistic performances, sip craft wine, beer, or cider, and savor food from on‑site vendors.
Admission is free!
The Hill School Centennial Auction and Gala
The Hill School, celebrating a century of education, character, and connection, invites the entire community back to campus for a Centennial Spring Weekend filled with energy, nostalgia, and plenty of Hill spirit. This special milestone honors the memories formed, lessons learned, and bonds that have shaped generations of students. Throughout the weekend, guests can enjoy campus gatherings, class meet‑ups, family‑friendly activities, and moments that bring Hill’s past and present together in the best possible way.
The celebration culminates in the Centennial Gala on May 9, a lively evening of music, dinner, dancing, and toasts to the next 100 years. It’s a chance to reconnect with old friends, make new ones, and celebrate the school’s enduring legacy with gratitude, joy, and anticipation for all that’s ahead.
Celebrate Mother’s Day in Middleburg
Middleburg offers plenty of ways to make Mother’s Day feel special, whether you’re planning a relaxed afternoon or an elegant outing. Treat Mom to a memorable supper at The Red Fox Inn & Tavern, where historic charm meets seasonal cuisine, or enjoy yoga and tea or brunch at Salamander Middleburg. For something more laid‑back, Lost Barrel Brewing offers great food, music, and wide‑open views perfect for a family gathering. And if she loves wine country, Boxwood Estate Winery provides a beautiful setting for a tasting flight and a slow, sunny afternoon.
However you celebrate, Middleburg has the perfect spot to make Mom feel appreciated!
Loudoun Therapeutic Riding Barn Dance
Loudoun Therapeutic Riding invites the community to the Boots Bridles & Bling Barn Dance on May 16th! In the Year of the Horse, this lively gathering brings friends, supporters, and neighbors together for a night filled with purpose, partnership, and plenty of fun.
Guests will enjoy a hearty dinner from Mission BBQ, along with local wine and beer. Throughout the evening, attendees can take part in a spirited live and silent auction, try their luck with cash games and a 50/50 raffle, and then head to the dance floor for a boot‑stomping night of music and dancing. Surrounded by LTR’s wonderful herd and the dedicated community that makes their mission possible, this event is more than just a barn dance—it’s a celebration of the life‑changing impact happening every day at LTR.
Land Trust of Virginia’s Garden Party
On May 17, you’re invited to the Land Trust of Virginia’s annual Garden Party—an afternoon dedicated to celebrating the people and partnerships that help protect Virginia’s open spaces, working farms, and historic landscapes. Each year, this gathering brings supporters together at a beautifully conserved private property for an elegant mix of fine food, drinks, live music, and easy conversation. It’s a chance to enjoy the season, connect with neighbors, and honor the ongoing work that keeps Virginia’s countryside thriving.
The Paradise Antiques Spring Open House
The Paradise Antiques invites the community to a special Two‑Day Open House celebrating the grand reveal of its newly expanded shop and the arrival of its latest collections from France. Guests are welcome to explore beautifully curated European antiques, browse new pieces sourced from recent buying trips, and enjoy the charm of a thoughtfully reimagined space designed to inspire collectors, decorators, and design enthusiasts.
This milestone weekend offers a chance for local residents, longtime supporters, and professional partners to experience the expanded shop, discover fresh finds, and share in the excitement of this new chapter for The Paradise Antiques.
Upperville Jump4Fun
Upperville Jump4Fun returns to the iconic Upperville showgrounds on May 30 and 31!
Jump4Fun offers riders a fantastic opportunity to compete over professionally designed courses on world‑class footing. This unrecognized show is ideal for riders of all levels, whether they’re bringing along a young horse, polishing their skills, or simply looking for a fun, low‑pressure day in the ring.
Saturday, May 30 will feature the Jump4Fun Hunter divisions and Sunday will feature the Jump4Fun Jumper classes. Entries open on May 1 and must be made through HorseShowsOnline.
Click below for the Prize List!