Fall doesn’t just arrive in Middleburg, it rolls in with misty mornings, hoofbeats in the distance, and the unmistakable scent of a new season. As always, October breathes life into a calendar full of local traditions. Whether you’re raising a glass at the Boxwood Vintner’s Pairing, taking a swing at the Hill School Golf Tournament, or catching up with neighbors at the VIVA Community Dinner, this month is about connection and rhythm.
Don’t miss the Cana Harvest Festival, Halloween Songs and Stories at Emmanuel, or the free Bryan Fox & Friends concert at the Community Center! Be sure to visit our full Events Calendar and not be left behind!
Virginia Piedmont Heritage Association Civil War Conference
Have you registered for the Virginia Piedmont Heritage Association’s 27th Annual Conference on the Art of Command in the Civil War? This amazing event is October 3-5, 2025 at Middleburg Community Center.
Bring a friend and receive 50% off their ticket! Email info@piedmontheritage.org or call 540-687-6681 with questions.
VPHA has assembled a panel of nationally renowned Civil War scholars to explore the momentous events that took place during the 1862 Valley Campaign. Learn about the decision making and personalities involved that led to the tumultuous battles in the Valley of Virginia.
Bring a friend and receive 50% off their ticket! Email info@piedmontheritage.org or call 540-687-6681 with questions.
VPHA has assembled a panel of nationally renowned Civil War scholars to explore the momentous events that took place during the 1862 Valley Campaign. Learn about the decision making and personalities involved that led to the tumultuous battles in the Valley of Virginia.
Floating Sound Bath at Salamander Middleburg
Come float with Salamander and enjoy a magical sound bath experience. Imagine lying on a comfortable air mattress, as a symphony of sounds envelops you. Floating sound baths are a meditative experience where participants float weightlessly in water while being immersed in the calming vibrations of crystal singing bowls, and other instruments, promoting relaxation and rejuvenation.
Discover a new way of relaxing and rejuvenation while floating under the stars with warm blankets and eye masks. (You may also participate on land).
Choose from three dates or attend multiple times!
71st Virginia Fall Races at Glenwood Park
Celebrate one of Virginia’s most cherished sporting traditions at the Virginia Fall Races, returning to Glenwood Park on Saturday, October 11, 2025. Set against the beautiful backdrop of protected countryside, the Virginia Fall Races offer an exciting day of steeplechase competition paired with family-friendly activities for all ages.
In addition to exciting races, enjoy local food trucks, a lively Kids’ Fun Fair, and Stick Horse Races! It’s the perfect way to spend a fall day outdoors.
While Reserved Spaces are sold out, General Admission passes are available online now! Purchase in advance or pay $50 (cash only) at the gate and make the most of race day!
Middleburg Film Festival, October 16-19
Since 2013, the Middleburg Film Festival has delivered four incredible days of film, conversation, and unforgettable scenery!
Enjoy a curated selection of narrative and documentary films, including festival favorites, Oscar contenders, and world premieres, all shown in intimate theaters nestled in the heart of Middleburg.
Stick around for Q&As and conversations with acclaimed filmmakers, actors, and special guests. It’s a must-attend event for film lovers and storytellers alike!
Land Trust of Virginia’s Sunset in the Field, October 19
The Land Trust of Virginia’s Sunset in the Field at Farmer’s Delight on October 19th is the perfect fall outing!
Bring the whole family, pull on your boots, and join LTV for Bluegrass and BBQ against the breathtaking backdrop of the Blue Ridge Mountains, the very views we work to protect.
Enjoy live music from the renowned Lonesome River Band, delicious local BBQ, and fun for the kids, including a scavenger hunt, face painting, and more.
It’s a celebration of community, conservation, and the beauty of the land we love.
Hot Dog! It’s Halloween and MBPA/Middleburg Police Department Parade
Attention Middleburg ghosts, goblins and witches! The MBPA and Middleburg Police Department Halloween Parade is coming your way!
Gather at Middleburg Community Center at 4:45 pm on Friday, October 31 in your best costumes and parade through Town, trick or treating at local businesses along the way with Police Chief Shaun Jones.
After the parade, bring your appetites to Hot Dog! It’s Halloween at the Middleburg Community Center. This event is free of charge, so bring your family and friends and get ready to have a spooktacular time!