Middleburg stays in motion this June, where warm days bring a full calendar of outdoor adventures and celebrations of small-town life. From lively festivals and historic Juneteenth commemorations to toe-tapping music and mouthwatering local fare, the town is alive with community spirit and family-friendly fun. Local farms, wineries, and markets are bursting with the fresh flavors of the Virginia Piedmont, ready to be savored. Whether you’re wandering down charming streets, enjoying live performances, or simply relaxing in the scenic countryside, Middleburg invites you to slow down, soak it all in, and make the most of summer’s magic.
New events are always being added, so be sure to visit our full Events Calendar and not be left behind!
The 172nd Upperville Colt & Horse Show
Get ready for a timeless tradition as the 172nd Upperville Colt & Horse Show returns in 2025, bringing equestrian excellence and historic charm to Virginia’s countryside. Founded in 1853, it’s the oldest horse show in the United States and continues to draw top riders, trainers, and horse lovers from around the world.
Set beneath the towering oaks of Grafton Farm and the protected open space of Salem Farm, this week-long celebration features world-class competition, family-friendly events, boutique shopping, and local food and wine. Whether you’re a lifelong equestrian enthusiast or simply seeking a uniquely Virginia experience, the Upperville Show is a can’t-miss summer highlight filled with grace, tradition, and community spirit.
Parking and General Admission are FREE all week long!
Juneteenth Celebrations, June 19 and 21
Join Chloe’s of Middleburg on June 19 for a charming shopping experience and a special gift with purchase. Then head to the Piedmont Club in Haymarket for a unique wine pairing dinner with Chef Pete Smith and Kindra Dionne! Click here for more information!
The Middleburg Museum will host a day long Juneteenth Celebration beginning with a reading by Mrs. Marilyn Dillion at 11:30 a.m. A Walking Tour of African American Sites in Middleburg on June 19 will follow at noon and the day will conclude with a film screening at Mickey Gordon Park at 2:00 p.m. Click here for more information!
The Town Juneteenth Celebration will be Saturday, June 21 from 1-5 pm at Middleburg Community Center.
Bluegrass at the Barn
Attention Bluegrass fans of all ages!
Mt. Defiance Cidery & Distillery invites guests to enjoy Bluegrass at the Barn, a free, family-friendly event featuring live music by Shade Tree Collective and a selection of handcrafted hard ciders.
Visitors are encouraged to bring blankets, lawn chairs, and the whole family—or arrive early to grab an outdoor table.
Seasonal favorites like their refreshing Strawberry Cider and other specialty summer drinks will also be available, making it the perfect way to spend a laid-back afternoon in Middleburg.
Open Late Concert at National Sporting Library & Museum
On June 27th, the National Sporting Library & Museum (NSLM) welcomes The Silver Tones Swing Band to its Open Late Concert stage for an evening of lively music and community fun.
From 6:00 to 8:00 p.m., guests are invited to bring chairs or blankets and enjoy a free concert on the museum’s scenic lawn.
Both the performance and museum admission are free and open to the public.
Picnics are encouraged (no glass containers, please) and leashed pets are welcome.
See you there!
Once-Upon-A-Time Magic Show at Middleburg Library
The Middleburg Library invites families to experience a spellbinding blend of fairy tales and magic with the Once-Upon-A-Time Magic Show, presented by Dean Alan, the Wizard of Reading.
This enchanting performance brings beloved stories to life through whimsical illusions and magical surprises, creating a world where imagination knows no bounds. Perfect for children and families, the show promises a delightful journey filled with wonder and a touch of happily-ever-after.
Stuff the Cruiser for Seven Loaves
On June 27, the Middleburg Police Department will host its Stuff the Cruiser Food Drive at the Middleburg Safeway, supporting Seven Loaves Services in their mission to fight local food insecurity.
Community members are encouraged to stop by, say hello to the officers, and help fill a police cruiser with non-perishable food donations.
It’s a simple but meaningful way to give back and support neighbors in need. Every donation—big or small—makes a difference!
Oak Spring Garden Foundation Tours
Discover the beauty and legacy of Rachel “Bunny” Mellon at the Oak Spring Garden Foundation in Upperville June 27 & 28. Enjoy a self-guided tour through the formal walled garden and explore the Fantastic Flora exhibit.
Inside the Gallery, view “The Final Resting Place of President John F. Kennedy: The Untold Story of a Lost Memorial,” featuring a little-known design by Jean Schlumberger with support from Mellon, and artwork by Oak Spring alumna Sara Lindsay.