- Visitors & Events
- Signature Events
Middleburg is the home to a variety of special events and activities. See below for the Town's Signature Events, as well as other nearby events.
For the latest listing of ALL events in and around the Town, please visit the Visit Middleburg website at http://www.visitmiddleburgva.com
- View Special Events
- Christmas in Middleburg
- May - Art in the Burg
- JuIy - Independence Day
- August - National Night Out
- September - Oktoberfest
- October - 1000 Miglia Rally
- Sidewalk Sales
- Middleburg Spring Races
- Middleburg Hunt Point-to-Point
- Middleburg Film Festival
- Upperville Horse Show
- Virginia Fall Races
- Middleburg Wellness Day
Christmas celebrations kick off the first Saturday in December, rain or shine.
Read more about all of our Christmas and Holiday activities at this link!
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 - held the Friday evening before Christmas in Middleburg!
Learn more about Christmas in Middleburg.
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.
The Town of Middleburg will host Independence Day celebrations at the new Town Hall Village Green on July 4, 2023.
Stay tuned for more details!
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.
Middleburg Oktoberfest continues to be an amazing event - and 2022 was the best yet!
THIS YEAR we had two biergartens, traditional German food, live music, and festival games.
Mark your calendar for September 16, 2023 for this year's Oktoberfest!
This event has something for everyone including, authentic Oktoberfest games (feats of strength!). All the details are available at our dedicated webpage: middleburgva.gov/oktoberfest - and the latest updates are available by "Liking" our Facebook Page: facebook.com/middleburgoktoberfest .
The Town of Middleburg once again hosted the 1000 Miglia Warm-Up USA in October 2022!! Visit our main page on the 1000 Miglia for more details about the event and to find photos and a recap video. We can't wait to see you in October 2023 (dates TBD)!
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!
For more information about either sale, visit the Visit Middleburg website.
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.
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.
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 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.
The Town looks forward to bringing back a Wellness Day in the near future. Stay tuned!