April in Middleburg is a breathtaking sight, as the countryside awakens in a flourish of vibrant greens and colorful blooms. The rolling hills are dotted with blossoming trees, and the air is filled with the sweet scent of spring. The countryside comes alive with activity, as we embrace the long-awaited arrival of the spring. As the season unfolds, so does a calendar full of exciting events—from steeplechase racing to art shows, wine tastings, and community celebrations. April is packed with unforgettable experiences in the heart of Virginia’s hunt country, and we look forward to seeing you!
New events are always being added, so be sure to visit our full Events Calendar and not be left behind!
Middleburg Wellness Day and Fun Run
The Town of Middleburg invites one and all to participate and enjoy the 2025 Middleburg Wellness Day which will take place on Saturday April 12!
The Town of Middleburg invites one and all to participate and enjoy the 2025 Middleburg Wellness Day which will take place on Saturday April 12!
Wellness Day kicks off at 7:30 am with the Middleburg Wellness Day 5K & Kids Fun Run, followed by the Wellness Day Program, beginning at 10 am. This special event will highlight the numerous businesses and organizations in and around Middleburg that contribute to the many aspects of health and wellness and will be there to connect with, as well as presentations from local experts, swag, giveaways, and more!
Sip & Celebrate with the Windy Hill Foundation
Join the Windy Hill Foundation on April 17 at Salamander Middleburg for a relaxed and festive spring Soirée at Salamander Middleburg to celebrate the Windy Hill community and honor those who have shaped our mission.
Together, we will induct our newest Emeritus members, Judy Washburn and Helen Wiley, while offering a special tribute to the lasting contributions of Lang Washburn and John Levis.
Questions? Contact Eloise Repeczky at eloise@windyhillfoundation.org or call 540-687-3997.
Middleburg Spring Races
The Middleburg Spring Races return to Glenwood Park on April 19, bringing a day of thrilling steeplechase competition, rich tradition, and scenic Virginia countryside. As one of the oldest steeplechase events in the country, the races attract top horses, jockeys, and spectators for a day of high-speed action over timber and hurdle courses.
Enjoy tailgating, elegant hospitality tents, and the camaraderie of equestrian enthusiasts. Set against the rolling hills of Middleburg, this annual event offers an unforgettable experience that blends sport, history and open space.
Maclean: A Fly-fishing Family’s Literary Legacy
Join the NSLM on April 24 at 5 pm for a cocktail reception and discussion with award-winning journalist and author John N. Maclean.
John, son of Norman Maclean—author of A River Runs Through It—will discuss the new Library exhibition, The Art of the Angle, featuring original wood engravings from three classic fly-fishing books: A River Runs Through It, Home Waters, and Big Two-Hearted River: The Centennial Edition. He will explore the creation of these engravings and their connections across the works.
The exhibition highlights engravings by Barry Moser, Wesley W. Bates, and Chris Wormell, uniting and enhancing these literary landmarks.
The evening concludes with a book sale and signing.
John N. Maclean, a former Chicago Tribune correspondent, is a noted author of fire literature and an avid fly fisherman.
Middleburg Humane Foundation Denim & Diamonds Sparkle & Strut Disco Gala
Don’t miss the Middleburg Humane Foundation’s Denim & Diamonds Sparkle & Strut Disco Gala on April 26! This great evening at The Middleburg Barn, where all the support generated will support Middleburg Humane Foundation and all of the animals we care for at our 23-acre facility.Don’t miss the Middleburg Humane Foundation’s Denim & Diamonds Sparkle & Strut Disco Gala on April 26! This great evening at The Middleburg Barn, where all the support generated will support Middleburg Humane Foundation and all of the animals we care for at our 23-acre facility.
Passed hors d’oeuvres, the pescatarian buffet is catered by Susan Gage. After dinner, make sure you have your dancing shoes on to Sparkle and Strut with The DC Transit Band! And a live auction offering some items you won’t find anywhere else!
River’s Journey Exhibit at The Byrne Gallery
The Byrne Gallery announces their March show, The Poetry of Spring. This show will feature six local artists: Suzanne Lago Arthur, Miguel Diaz, Gerald Hennesy, Cathleen Lawless, Matt Tymowski and Carolyn Marshall Wright. On display from March 1-30, 2025. Come celebrate the classic beauty of still life paintings as we welcome spring!
The Byrne Gallery is open Wednesday to Saturday, 10 am to 5 pm and by appointment.
Arbor Day Celebration at the Upperville Horse Show’s Grafton Farm
Celebrate Arbor Day Under the Oaks at Historic Grafton Farm Showgrounds, an easy addition to Garden Club of Virginia’s Historic Garden Tours!
Bring a picnic, take a self-guided tour under the iconic tree canopy, explore the stream and wildlife habitat.
Admission is free. Dogs must be leashed and vaccinated. Please clean up after your pets.
Grafton Farm (the “Hunter Side”) is located at 8321 John S. Mosby Highway, Upperville, VA 20184. (South side of the Upperville Showgrounds on Route 50 in Upperville, Va.)