Autumn is on her way to Middleburg! Come experience the change of season in our teeny, tiny town and take advantage of all we have to offer. The featured events below are just a small sampling of what Middleburg has in store for you this month, as we can’t wait to see you early and often!
As always, be sure to visit our full Events Calendar to keep up with additions!
Grafton Hunter Show at the Upperville Showgrounds
The Upperville Colt & Horse Show invites the community to show “Under the Oaks” at the Grafton Hunter Show on Saturday, September 7, 2024!
This unrecognized horse show will be held in the main “Parker” Hunter ring with open seating for spectators in the Grandstand.
Classes will start at Hilltopper and progress through 2’3″-2’9″, ending with the 3′ $2,000 Grafton Derby, and will offer high point awards for Amateur rider, Junior rider, Professional rider and Grand Champion horse, as well as a $500 cash prize for the hunt accumulating the most points from its members competing.
Proceeds will benefit the UCHS Jump In! Capital Campaign.
Silhouette Artist at the PLAYroom
PLAYroom will be hosting silhouette artist, Erik Johnson!! Erik is a highly skilled, third generation silhouette artist, who learned the craft from his father.
Within minutes, Erik hand cuts each silhouette by just looking at the subject’s profile. When he’s done, you’ll have an amazing keepsake silhouette of you, your child, significant other, etc. Silhouettes make great gifts!
Signups are FREE!
Silhouettes are $30 each, duplicate of the same person is $15.
Framing is available. Cash and credit cards accepted.
National Sporting Library & Museum Polo Classic
The 2024 National Sporting Library & Museum Polo Classic presented by MARS EQUESTRIAN™ will take place on Sunday, September 15th, at Great Meadow in The Plains, Va.
Proceeds from the NSLM Polo Classic presented by MARS EQUESTRIAN™ benefit the NSLM in its 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 help support dynamic exhibitions, programs, and community events throughout the year.
Middleburg Oktoberfest
The Middleburg Oktoberfest Celebration is on Saturday, September 21st! Festivities will take place on South Madison St. and Federal St., which will be closed to vehicular traffic.
Oktoberfest will feature two 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, and Artists’ Alley returns exhibiting work of local and regional creators!
Save the Date: Land Trust of Virginia’s Sunset in the Field
Looking for a spectacular fall event? Grab the family, polish your boots, dust off your “goin’ to the farm” hat, and join us for LTV’s 4th annual Sunset in the Field Party!
Come chill with us and enjoy Bluegrass and BBQ while watching the sunset behind the Blue Ridge Mountains. After all, isn’t the preservation of that spectacular landscape what it is all about?
This year’s event will feature Lonesome River Band, one of the most respected names in bluegrass music.
First Annual Rokeby Community Festival
OSGF is thrilled to invite you to the Rokeby Community Festival, where guests of all ages can get into the fall spirit with friends and family, featuring:
-A pickleball tournament on the Rokeby Airstrip
-Plant Sale
-Live music from local artists
-Food trucks and local libations
-Family fun activities such as: scavenger hunts, relay races, mazes, face painting, food demos, and more!
-Educational plant talks and field walks.