Search

The Middleburg Business & Professional Association

Main Menu

Local Events in Middleburg

Come & Join the Fun!

Renowned as the Nation’s Horse & Hunt Capital, Middleburg offers a variety of equestrian events throughout the year, including the Middleburg Spring Races and the Virginia Fall Races. It’s also a well-known destination for the arts with events like the Middleburg Film Festival and Art in the Burg.

Christmas in Middleburg draws thousands of visitors, who line the streets on the first Saturday in December to watch the parade and the Middleburg Hunt Revue.

Check the calendar below to find out what’s happening around town.

Audience in lawn chairs clapping in front of National Sporting Library and Museum
Monthly Weekly Daily List
May 2026

Places in My Heart

This May, The Byrne Gallery will showcase five artists—Craig Arnold, Laura Bollettino, Katie Flack, Tobin Karicher, and Anne Stine—as they present their most cherished interpretations of the landscapes that inspire them. Their paintings invite viewers on a journey through the season of renewal. Additionally, an artists’ reception will be held on May 16 from 4–7 pm, […]
May 06 - 31
8:00 am - 6:00 pm
The Byrne Gallery
7 W Washington St, Middleburg, VA 20117
View Detail

Hill School Spring Weekend & Centennial Gala

The Hill School, celebrating a century of education, character, and connection, invites the community to return for a Spring Weekend honoring the memories formed, lessons learned, and bonds that endure. This Centennial gathering pays tribute to the past, embraces the joy of the present, and looks ahead with gratitude and anticipation to the next 100 […]
May 08 - 09
8:00 am - 6:00 pm
View Detail

“The Animal in Art: Highlight the Horse, Fox and Hound” Exhibit

The Artists in Middleburg annual Animals in Art: Highlighting the Horse, Fox and Hound exhibition celebrates the beauty, spirit, and tradition of the horse, fox, and hound. This show honors the animals that are central to our region’s landscape and heritage. It represents 50 local artists with all new work.
May 09 - Jun 14
All Day
The Artists in Middleburg
102 W Washington St, Middleburg, VA 20117
View Detail

Live Music Series with Dennis Wayland

Join Cana Vineyards for their live music series! Dennis Wayland is a singer/songwriter from Manassas, Virginia who has a five song EP that was recorded in Nashville called Between Love and Rock N’ Roll as well as two solo albums to his credit. The music he writes is heavily influenced by classic country ballads, southern […]
May 09
12:00 pm - 4:00 pm
Cana Vineyards & Winery
38600 Little River Turnpike, Middleburg, VA 20117
View Detail

Mother’s Day Supper

Treat Mom to an unforgettable Mother’s Day at The Red Fox Inn & Tavern. Enjoy a refined three-course supper featuring seasonal flavors and time-honored culinary techniques in an elegant, welcoming setting. It’s the perfect way to celebrate and spend meaningful time together. Click here for reservations! 
May 10
11:00 am - 3:30 pm
Red Fox Inn & Tavern
2 East Washington St, Middleburg, Va 20117
View Detail

Mother’s Day Brunch

Bring the whole family to Boxwood this Mother’s Day and feel right at home. Menu: Individual basket of handmade pastries, tender prime rib drizzled with red wine demi-glace and horseradish crema, golden hash brown casserole, a custom omelet station with gourmet toppings, crisp Caesar wedge salad, and decadent handmade chocolate truffles. Each ticket includes a […]
May 10
11:00 am - 12:30 pm
Boxwood Estate Winery
2042 Burrland Ln, Middleburg, VA 20117
View Detail

Mother’s Day Brunch

Bring the whole family to Boxwood this Mother’s Day and feel right at home. Menu: Individual basket of handmade pastries, tender prime rib drizzled with red wine demi-glace and horseradish crema, golden hash brown casserole, a custom omelet station with gourmet toppings, crisp Caesar wedge salad, and decadent handmade chocolate truffles. Each ticket includes a […]
May 10
1:00 pm - 2:30 pm
Boxwood Estate Winery
2042 Burrland Ln, Middleburg, VA 20117
View Detail
No event found!

Want to submit your event?

Anyone in the local Middleburg area can easily submit an event online!

Submit Event