— May is a month of enjoyment, celebration and regeneration, with bright weather, blossoming flowers and singing birds, all of which is exemplified in our little corner of the world.

With Foxes on the Fence, Art in the Burg, Mother’s Day brunches galore as well as new and exciting exhibits and events, there is no shortage of ways to enjoy the “Merry Month of May” in Middleburg!

Foxes on the Fence: Bid on Your Favorite Critter

Foxes and hounds and hares, oh my!

The Town of Middleburg transforms into a walking art exhibit with painted foxes, hounds and hares from April 1- May 13, 2023.

Bid on your favorite critter masterpieces in the online auction from April 2 at Noon until May 13. Winners may pick up their critters after 4 pm at Art in the ‘Burg on May 13. All proceeds support Middleburg Beautification and Preservation and the Middleburg Arts Council.

Windy Hill at 40! Celebrate on May 4th

Windy Hill is proud to have entered their 40th year of Making a Difference in our neighborhood. All are welcomed to celebrate this incredible milestone with the community!

Thursday, May 4, 2023
6-8 pm
Salamander Resort & Spa
500 North Pendleton St

The entire Windy Hill Family – past and present- will be honored. Raise a toast to our beloved volunteers, devoted staff, Board members and treasured partner organizations.

Art in the Burg is Back

=Art in the Burg is Middleburg’s annual celebration of the arts, Saturday, May 13!

The day begins with The Art of the 5k Run/Walk at the Community Center at 8 am and Art in the Burg is open from 10 am to 6 pm on South Madison and Federal Streets. Enjoy a variety of local and regional artists, activities, food and fun, at the festival held along South Madison and Federal Streets.

Other highlights include Foxes on the Fence, fashion show, live music, cooking demonstrations with local chefs and street theater performances!

DocWeek Middleburg

Doc Week Middleburg is back at the Middleburg Community Center May 16-20, 2023!

DocWeek Middleburg Film Festival (formerly Doc5) is one of the area’s most intriguing and enjoyable cultural events. Showing 5 films in 5 days in the beautiful Shenandoah Springtime, the festival is a chance for documentary film lovers to be informed, be delighted, or both.

This year, DocWeek will present a variety of films with subjects varying from the Dalai Lama to the sale of North Korean nuclear warheads to an evening of superb jazz.

American Craft Beer Week at Lost Barrel Brewing

Join Lost Barrel Brewing May 18-21 in celebration of American Craft Beer Week!

American Craft Beer Week is celebrated to give independent breweries and local beer makers a chance to make a mark on the global market. In the U.S. alone, there are more than 500 independent breweries, which look forward to this week to compete with their global competitors.

What better way to celebrate than at your favorite local brewery?

Lost Barrel is open Thursday to Sunday. Questions? Email contact@lostbarrel.com.

Virginia Piedmont Heritage Association Trail Ride

Join Virginia Piedmont Heritage Association and enjoy an exclusive trail ride through the National Register listed “Little River Rural Historic District” which will explore the history of the most pristine territory of the Orange County Hounds.

The ride will begin at the early 19th-century Westbourne and continue across the legendary estates of Oakendale and Stonehedge.

The entire ride will take place on properties permanently protected by conservation easements.

Additional Events

Did we miss something? Email us at info@visitmiddleburgva.com or DM us on social media to let us know!