Traditional Activities

Christmas celebrations kick off the first Saturday in December, rain or shine. Celebrations make for a Christmas experience like no other, featuring:

• Breakfast with Santa
• Christmas Parade
• Craft Fair
• Middleburg Hunt Review
• Spirits of Middleburg

Also, don't miss the Annual Christmas Tree Lighting Ceremony is held the Friday evening before Christmas in Middleburg! Learn more about Christmas in Middleburg.

The Town of Middleburg is excited that the 1000 Miglia Warm-Up USA will be returning in October 2022!! Visit our main page on the 1000 Miglia for more details what to expect and for an awesome video from 2019. We can't wait to share more details with you.

Join the Middleburg Arts Council during their annual celebration, featuring artwork from more than 20 local and regional artists. Art lovers will get the opportunity to purchase original works without gallery fees. While you're here, visit Middleburg's many restaurants and quaint shops. This event occurs on the second Saturday in May and is held in downtown Middleburg.

Learn more about Art in the Burg from the Art Council page.

Join us at the Middleburg Community Center for our annual Fourth of July celebration! Children’s parade, music, swimming, food, events & fireworks.

Learn more about the annual Fourth of July Celebration.

The Middleburg Film Festival is four days of fantastic films in a spectacular setting!  Films include:

• Academy Award Contenders
• Festival favorites
• First-class foreign films
• World premiers

Learn more about the Middleburg Film Festival.

The Middleburg Hunt Point-to-Point is held annually the last Saturday in April at Glenwood Park. Enjoy the exciting sport of steeplechase racing at one of the most beautiful race courses in the nation!

Learn more about the Middleburg Hunt Point-to-Point.

NOTE FOR 2022:  The Middleburg Spring Races will be held on April 23, 2022. 

Held annually on the 3rd Saturday In April at Glenwood Park, the Middleburg spring races are Virginia's oldest steeplechase! Come see the nation's most athletic thoroughbreds compete at high speeds over hedges and timbers - tailgating at its best.

Learn more about the Middleburg Spring Races.

Held annually the first Tuesday in August, join the Middleburg Police Department in their annual community-building campaign to promote strong police-community partnerships and build neighborhood camaraderie. Features include:

• Bounce house
• Dunk tank
• Free food and beverages
• Rock climbing wall

Learn more about the annual National Night Out.

Winter Sidewalk Sale

The Middleburg Business and Professional Association plays host to an annual Winter Sidewalk Sale held during the Presidents Day weekend in February (Friday, Saturday and Sunday). Look for the blue and white balloons at local businesses who participate in this event. Find wonderful items at great prices!

Summer Sidewalk Sale

The Summer Sidewalk Sale is held during the first weekend in August (Friday, Saturday and Sunday)

The Middleburg Business and Professional Association hosts an annual Summer Sidewalk Sale each year to coincide with the Virginia Tax Relief Weekend. Look for the blue and white balloons at participating local businesses!

Additional Information

For more information about either sale, visit the Visit Middleburg website.

The Upperville Horse Show is held annually the first full week in June - more than a horse show - a fixture on the equestrian calendar!  The show is the oldest horse show in America, and features the nation's top ranking hunters and jumpers competing alongside local ponies, sidesaddle ladies and racing Jack Russell Terriers.

Learn more about the Upperville Horse Show.

The Virginia Fall Races happen the second Saturday in October at Glenwood Park. Experience the annual fall tradition in Middleburg's hunt country. Watch steeplechase action at the oldest continuous race course in Virginia.