June in Middleburg always has a little extra spark to it, especially as the fields green up, the barns get busier, and the equestrian heartbeat of the area settles into its summer stride. The month ahead brings a mix of long‑standing traditions, outdoor gatherings, and the easy flow that comes with summer days and lightning‑bug‑filled nights. The mornings start earlier, the days feel bigger, and the whole area takes on that unmistakable early‑season energy — the kind that moves almost unnoticed until you look up and realize summer has arrived!
As always, be sure to visit our full Events Calendar for the latest updates. There is never a shortage of activity in our little corner of the world!
173rd Upperville Colt & Horse Show
The 173rd Upperville Colt & Horse Show, the Nation’s Oldest Horse Show, returns June 1–7, 2026, to the Grafton and Salem showgrounds! Highlights include the $25,000 Thoroughbred Hunter Derby, the $25,000 International Hunter Derby, elegant Sidesaddle, beloved Leadline and walk‑trot classes for kids, and four days of FEI/CSI 4* show jumping.
Visitors can explore Vendor Village’s mix of local makers and returning show staples and stop by Art Under the Oaks, where local artists bring creativity to life for kids throughout the week. The Horses & Horsepower Car Show is also on site for those who want to swing through on Sunday.
Parking and admission are free all week long, making it easier than ever to spend your days ringside!
Sprout on the Green Golf Tournament
Round up your friends, neighbors, colleagues, and business partners and tee off for a cause at the 2026 Sprout on the Green Charity Golf Tournament. Enjoy 18 holes along the Potomac River, an open beverage cart, great food, exciting prizes, and a full raffle table — everything you need for an incredible day on the course.
What makes it even better is knowing your participation helps provide life‑changing equine‑assisted services to hundreds of individuals with disabilities. Your day of golf becomes something more, a chance to create opportunities, empower riders, and strengthen the community. A great round is always fun, but making an impact while you play is unforgettable.
Imagine Life Coaching Middleburg Retreat
Imagine Life Coaching hosts a restorative day on June 14 at 22865 Foxcroft Rd, centered on reflection, renewal, and personal alignment. Guests will move through mindful practices, creative exploration, and time in nature, including an Enneagram session, purpose‑alignment work, a farm‑animal stroll, journaling, group conversation, Tai Chi with sound healing, and floral arranging with Etten’s Eden. A private chef will prepare farm‑to‑table meals, creating a thoughtful pause in the middle of June and rounding out a peaceful day designed to support well‑being during this season of transition.
Tour Tuesdays at Foxcroft June 16-August 11
Foxcroft School welcomes friends and prospective families to Tour Tuesdays, an in‑person look at daily life on campus every Tuesday from June 16-August 11, 2026. Guests will enjoy a student‑guided walk across the 500‑acre grounds, meet community leaders and educators, and share a relaxed “summer camp” lunch in the dining hall. The visit offers time to see classrooms in action, hear about academic and residential life, and get a sense of the traditions that shape the Foxcroft experience.
Visitors may also explore the equestrian facilities, take part in an optional interview, and head home with a gift card to a local Middleburg coffee house.
It’s an easy way to experience the rhythm of campus and meet the people who shape it!
Middleburg Juneteenth Celebrations
Middleburg marks Juneteenth with two days of celebration, history, and community gatherings.
On June 19 from 11 am to 2 pm, The Middleburg Museum hosts 1776 to Juneteenth: Expanding Freedom, a look at the holiday’s origins and its place in the American story. The celebration continues on June 20 from 12-4 pm with a Juneteenth Block Party at the Middleburg Community Center with the Town of Middleburg and the Middleburg Police Department. The afternoon includes a free concert with Bryan Fox & Friends, plenty of food including pizza and ice cream, free face painting, and free swimming at the MCC pool. A Juneteenth Celebration and book signing with author Kevin Grigsby follows at 7 pm, along with special guest speakers and Black‑owned vendors, rounding out a day centered on community and reflection.
Father’s Day Festivities in the Burg
Middleburg is rolling out two great ways to celebrate the dads, granddads, and father‑figures who make life a little steadier, funnier, and better every day.
At Boxwood Estate Winery, Father’s Day brings a relaxed Surf & Turf afternoon with perfectly paired wine and an elevated menu. Adults can enjoy the Surf & Turf offering, while kids (12 and under) have chicken nuggets, mac and cheese, fresh fruit, and soft beverages. Enjoy a warm, vineyard‑side way to treat the guy who deserves a great meal and a slow afternoon.
At Lost Barrel Brewing, the celebration continues with live music, great food, and a laid‑back setting. Live music begins at 11 with Juliet Lloyd and continues until 5 pm with Two of the Four. The full menu runs all day, with brunch from 11:00 am to 2:00 pm and is ideal for dads who love good food and good music.