As April unfolds in Middleburg, the landscape seems to take a long, deep breath. Soft greens have returned to our fields, horses flick their ears toward warmer breezes, and Middleburg is humming with activity. April unfurls, inviting you to notice the shift in light, the renewed energy in familiar places, and the subtle beauty that only our little corner of the world reveals when the seasons turn. There’s a sense of awakening everywhere, not loud or showy, but steady and full of promise. This April, let Middleburg’s gentle momentum carry you into what’s next! We will see you soon!
As always, be sure to visit our full Events Calendar for the latest updates. We are always adding more!
The Hill School Spring Celebrations
The Hill School has an exciting season ahead, filled with moments you won’t want to miss. On April 12, the Hill School Sporting Clays Invitational returns to Oak Spring Farm in Upperville— an opportunity to enjoy a premier sporting clays course set against sweeping countryside views, all in support of The Hill School. Registration and sponsorship opportunities are now open for this standout event.
Then, on May 8–9, Hill’s Centennial Spring Weekend invites alumni, parents, faculty, and friends back to campus for a celebration a century in the making. It’s a chance to reconnect, honor the past, celebrate the present, and look confidently toward the next 100 years of Hill.
Upperville Garden Club Daffodil Show
The Upperville Garden Club will host the 61st Annual Daffodil Show at Trinity Church in Upperville on April 7 from 2-5 pm. This is a beloved tradition that celebrates the charm and diversity of these bright spring blooms. Local exhibitors and flower enthusiasts are encouraged to take part and enjoy an impressive display of daffodil varieties, from classic favorites to more unusual cultivars. The event is free to attend, and complimentary food and beverages will be available for all exhibitors and guests, creating a relaxed, welcoming atmosphere for anyone who appreciates the beauty of the season!
Middleburg Spring Races
Virginia’s oldest steeplechase tradition returns as the Middleburg Spring Races make their way back to Glenwood Park on Saturday, April 18. Post time is 1 pm.
This celebrated event blends the thrill of world‑class racing with the unmistakable charm of Middleburg’s countryside, drawing longtime racegoers and newcomers alike to one of the region’s most iconic settings. From the athleticism on the course to the vibrant community spirit around it, the day captures everything that makes spring in hunt country feel electric.
Passes are now on sale, offering your chance to be part of a legacy that has delighted spectators for generations!
Middleburg Humane Havana Nights Gala
Get ready for an unforgettable evening at the Middleburg Humane Foundation’s Havana Nights Gala at The Middleburg Manor on April 25th!
Guests will be swept into a night bursting with color, rhythm, and incredible company, all in celebration of a great cause. Expect a flavorful pescatarian buffet, elegant passed hors d’oeuvres, seamless valet service, a DJ who knows how to keep the energy high, and a photo booth ready to capture every spontaneous, joy‑filled moment.
But the magic goes beyond the music and the menu. Havana Nights brings the community together to make a real difference for animals in need. Each ticket helps provide care, compassion, and the second chances every animal deserves. It’s a party with heart, and you’ll feel it from the moment you arrive.
Middleburg Wellness Day, 5k, 10k, and Kids Fun Run
Middleburg Wellness Day returns on Saturday, April 25, bringing a full morning of movement and a full afternoon of inspiration. The day kicks off early with the 10K, 5K, and Kids Fun Run. Registration and check‑in open at 7:00 am, and the 10K gets underway at 7:45 am; the perfect way to get those hearts pumping and set the tone for a feel‑good day.
The activities continue at the Wellness Day Fair, held in the Ballroom and Terrace Room of the Middleburg Community Center from 10:00 am to 2:00 pm. The fair showcases the many businesses and organizations that support health and wellness throughout the Middleburg area.
Throughout the day, you’ll find engaging presentations, hands‑on demos, and fantastic giveaways curated by our vendors to help you take the next step in your wellness journey. It’s a day designed to energize, educate, and inspire.
Middleburg Hunt Point-to-Point
The Middleburg Hunt Point‑to‑Point Races return to Glenwood Park on Sunday, April 26, and the excitement is palpable! This beloved spring tradition delivers everything you love about a day in Virginia horse country: heart‑pounding races, lively tailgates, and that unmistakable springtime buzz.
Gates open at 10:00 am, giving you plenty of time to set up your perfect tailgate spread, catch up with friends, and soak in the views before the action begins. The first race goes off at 1:00 pm, kicking off an afternoon of thrilling competition as riders and horses take on the rolling course with speed and style.
Whether you’re there for the sport, the social scene, or simply the joy of a spring day outdoors, Point‑to‑Point offers a little something for everyone. Mark your calendar, gather your crew, and get ready for one of Middleburg’s most festive days of the season.