August is the perfect time to revel in everything Middleburg has to offer, including sunshine, shopping, and unforgettable events. Start the month with the beloved Summer Sidewalk Sale, where an array of items spill out onto the storefronts with colorful balloons, unbeatable deals, and summer finds you didn’t know you needed! Next, come together with friends and neighbors for National Night Out, an evening of community spirit filled with games, music, food, and fun for all ages. The Family Reunion at Salamander Middleburg returns for its fifth year! This high-energy weekend celebrates food, culture, and connection, featuring celebrity chefs, tastings, and unforgettable conversations. From front-porch chats to five-star feasts, there’s no better place to soak up the summer than right here in Middleburg.
New events are always being added, so be sure to visit our full Events Calendar and not be left behind!
Nineteenth Annual Summer Sidewalk Sale
Join the Town of Middleburg and the Middleburg Business & Professional Association for one of the most anticipated shopping weekends of the year! Stroll through charming downtown Middleburg and discover unbeatable deals from your favorite local boutiques and stores.
Sale Hours:
- Friday & Saturday: 10 AM – 5 PM
- Sunday: Hours vary by shop
Don’t miss this fun-filled summer tradition!
National Night Out
Join the Middleburg Police Department for National Night Out, a fun-filled evening that brings our community together with local law enforcement, first responders, and neighbors!
Enjoy family-friendly activities, meet your local police and learn how we can all help keep our community safe. There will be games, giveaways, and plenty of fun for all ages.
New this year: Help decide which Middleburg Police Officer kisses Sylvester the Ram!
Cast your vote by dropping money into the donation jar of your favorite officer. The officer with the most donations by 7 PM will earn the honor of puckering up and kissing our beloved Sylvester the Ram — all for a great cause!
All proceeds go to Seven Loaves Services, helping those in need right here in our community.
Join us for an evening of fun, games, and community spirit — and maybe a little sheepish smooching.
The PLAYroom Welcomes Music with Mowgli on August 10th
Looking for a playful, enriching activity to enjoy with your little one? Come connect with other parents and children at the PLAYroom during an engaging music session led by Mowgli.
Through interactive, play-based music activities, Mowgli will support key developmental milestones in areas such as communication, social skills, motor development, and emotional regulation.
Activities include singing, movement, instrument play, floor time (with chairs available for those who prefer), imaginative play, and more. A joyful, supportive space for you and your child to grow and bond!
Fifth Annual Family Reunion at Salamander Middleburg
Get ready for the fifth annual Family Reunion, an immersive experience celebrating diversity in the hospitality industry, which returns to Salamander Middleburg August 14–17, 2025.
Presented by renowned chef and author Kwame Onwuachi, in collaboration with Dotdash Meredith’s FOOD & WINE and Sheila Johnson’s Salamander Collection, this dynamic, multi-day event will once again impress. Attendees will experience thought-provoking panel discussions, hands-on cooking demonstrations, uplifting recreational activities, and meaningful “family” meals shared with celebrity chefs and industry leaders.
Don’t miss your chance to be part of this inspiring celebration of culture, cuisine, and community.
Dinner & Dive In Movie at Middleburg Community Center
Middleburg Community Center’s legendary Dinner & Dive In Movie returns Friday, August 15th from 5-8 pm!
Bring your swimsuit, towel, sunscreen and appetite for FUN to this beloved community event that includes dinner, swim time and a family film for all ages.
Check the Middleburg Community Center’s website for upcoming details!
Virginia Piedmont Heritage Association Presents The Wanzer-Grigsby Escape
On Christmas Eve, 1855 six men and women escaped from several local plantations, risking everything for a chance at freedom. Join the Virginia Piedmont Heritage Area to explore the remarkable true story of their death-defying journey.
Historians and educators Lori Kimball and Donna Bohanon of Oatlands and the Friends of Thomas Balch Library Black History Committee will provide an in-depth look at the history and legacy of one of the most famous episodes in the history of the Underground Railroad.
The event will be held August 28th at Slater Run Vineyards in Upperville.