September is on its way, and Middleburg is anything but quiet. The month brings familiar faces, favorite local spots, and plenty of reasons to make a trip into town. There are gatherings to catch up with friends, events to put on the calendar, and a few things you won’t want to miss. It’s the time of year when summer starts giving way to fall, but there’s still plenty of life happening around the Burg. Whether you’re a longtime local or just passing through, September is a good month to get out and see what’s happening! Here’s a look at what’s ahead!
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!
Middleburg Library’s Adult Book Club at Lost Barrel
Join the Middleburg Library’s monthly book group at Lost Barrel Brewing for a lively discussion of Trampoline by Robert Gipe, an award-winning author from Appalachia. The novel follows 15-year-old Dawn Jewell, a sharp, restless teenager who finds herself drawn into her grandmother’s fight against mountaintop removal mining.
The Appalachian Book Group explores works by authors from the region, offering readers a chance to discover new voices and discuss the stories, culture, and experiences that shape Appalachia. Pick up a copy of Trampoline at Middleburg Library and join the conversation. This group is open to ages 21 and older.
Book Signing with Marion Parsons at Federal & Black
Join Federal & Black on Saturday, September 12, from 2–5 pm for a special book signing with Marion Parsons, known to her longtime followers as Miss Mustard Seed. A paint enthusiast, artist, author, and champion of creativity, Parsons has built a career inspiring people to bring more creativity and character into their homes. She is the author of Feels Like Home, Inspired You, and her newest book, Move Slow & Make Things. Stop by to meet Marian, hear more about her creative journey, and get a signed copy of her latest book.
2026 Gallop Gala at Sprout Therapeutic Riding & Education Center
he Sprout Gala is Sprout Therapeutic Riding & Education Center’s annual celebration of service will be unforgettable!
The barn will be transformed into an enchanted, untamed jungle, creating a lush backdrop for cocktails, dinner, auctions and dancing.
Guests will enjoy signature drinks, a delicious dinner and exciting silent and live auctions, along with the chance to tour the barn, meet the horses and see Sprout’s programs in action during the premiere of the annual Impact Video. After dinner, the celebration continues with dancing to the lively sounds of Virginia’s favorite dance bands!
NSLM Polo Classic Presented by MARS EQUESTRIAN™
The 2026 NSLM Polo Classic presented by MARS EQUESTRIAN™ will take place on Sunday, September 13, at Great Meadow Foundation in The Plains, VA. Ticket sales are now open!
As the National Sporting Library & Museum’s sole fundraising event each year, the proceeds from the Polo Classic support the NSLM’s mission to preserve, promote, and share the literature, art, and culture, of equestrian, angling and field sports as well as advocate for the conservation of open space and waterways crucial to these sports. Funds raised from the event allow the Library & Museum to host dynamic public programs and fine-art exhibitions, as well as care for its world-renowned collection of nearly 22,000 works covering 500 years of history—all located in the heart of Middleburg.
The Polo Classic is a fun and festive day of polo and wonderful way to experience the NSLM’s mission first-hand. The event includes two top-tier polo matches, seated lunch in the Founders’ Pavilion, champagne divot stomp, traditional parade of the hounds, and much more!
Middleburg Oktoberfest Returns September 19th
Prost! Join the Middleburg Oktoberfest Celebration on September 19, 2026!
Festivities will take place on South Madison St. and Federal St., which will be closed to vehicular traffic. We’ll have multiple biergartens, traditional German food, live music, and festival games. Local beer, wine, cider, and traditional Oktoberfest foods will be available for purchase from local vendors.
We are also excited to bring back Artist’s Alley. Coordinated by the Middleburg Arts Council, artwork from local and regional artists will be available for purchase. Regional artisans will also be present throughout the day with exhibits of fine art, pottery, jewelry, wearable art and more!
Rokeby Community Festival Returns to Oak Spring Garden Foundation
The Oak Spring Garden Foundation invites you to the third annual Rokeby Community Festival, a celebration of agriculture, art, learning, and community in the heart of Virginia’s beautiful Piedmont. Bring the whole family for a fun-filled day featuring live music, local food trucks, beer and wine from Powers Brewery and Slater Run Vineyard, kids’ activities, educational talks and field walks, craft vendors, display exhibitions, and booths highlighting Oak Spring and other local environmental organizations.
Please note the festival takes place exclusively on the Rokeby property and does not include access to Little Oak Spring. For the safety of guests and the working farm, pets are not permitted. ADA-compliant service animals are welcome.