Jumpstart June in Middleburg

Jumpstart your summer in Middleburg this June and create memories to last a lifetime in our teeny, tiny town! Longer days, brighter weather and a virtually endless amount of fun await you, whether indoors or outdoors.

The Town of Middleburg Farmers Market (Saturdays 9 am to Noon) and the Buchanan Hall Farmers Market (Wednesdays 4:30-7:30 pm) are in full swing, bringing you a cornucopia of locally produced, fresh goods and artisan gifts.

The Upperville Colt & Horse Show, the Oldest Horse Show in the Nation, returns the first week of June and offers free parking and admission, exciting competition, fabulous shopping and delicious food vendors. The Middleburg Community Center Pool opens for its 75th season of keeping Middleburg cool, while the AiM Gallery offers art education for everyone. Oak Spring Garden Foundation’s Summer Plant Camp offers exciting outdoor education and fun for children ages 6-12 years.

Be sure to celebrate Dad this Father’s Day, June 16! Treat him to a day of relaxation, food and fun here in Middleburg, or, if he’s a history buff, give him tickets to VPHA’s “Chasing Jeb Stuart and John Mosby” event!

As always, be sure to visit our full Events Calendar to see what else may strike your fancy.

171st Upperville Colt & Horse Show presented by MARS Equestrian™

The Upperville Colt & Horse Show is June 3-9, 2024 at Grafton and Salem Showgrounds on Route 50 in Upperville. Admission and parking are free all week!

The show begins daily at 7:30 am and signature classes include the International Hunter Derby, Leadline, and the $226,000 FEI4* Upperville Jumper Classic. Experience this beloved 171-year-old tradition “Under the Oaks”!

Middleburg Community Center Pool is Open!

The Middleburg Community Center pool is open and will remain open on weekends until Friday June 14th for the end of school year pool party 5-8pm.

Beginning June 15th, the pool will be open daily 11am – 6pm through Labor Day.

Pool Memberships are available, but not required to swim. Dive in and spend the summer with the Community Center this summer!

Paws, Brushes & Pet Portraiture Class

Artist Heather Connole will lead AiM’s pet portraiture class, where you’ll learn to translate the unique essence of your beloved companion onto canvas.

Heather will guide you through the process, helping you choose your preferred medium and unraveling techniques to accentuate every detail of your pet’s features. With personalized instruction and step-by-step guidance, you’ll develop the skills needed to portray your cherished animal friend.

Oak Spring Garden Foundation Summer Plant Camp

Come to Oak Spring Garden Foundation this summer for Plant Camp! Where green thumbs and creative minds blossoms!

Plant-tastic activities are planned, including wild adventures filled with farm education, nature-based learning, engaging farm-to-table projects and story time in the garden for ages 6-9 and 10-12 years.

Father’s Day Festivities in Middleburg

What do you call an illegally parked frog?


Why did the scarecrow win an award?

Because he was outstanding in his field

Why don’t skeletons fight each other?

They don’t have the guts.

Dad jokes aside, we hope that you and your dad, father figure, fellow dads and dad friends take advantage of the Father’s Day Festivities in Middleburg on Sunday, June 16.

Click the button below for Father’s Day activities in which to partake!

VPHA Presents “Chasing Jeb Stuart and John Mosby”

Join author and renowned historian Bob O’Neill at Buchanan Hall as he returns to the Heritage Area to discuss his book “Chasing Jeb Stuart and John Mosby: The Union Cavalry in Northern Virginia from Second Manassas to Gettysburg”.

The program will be followed by a beer & wine reception.