Long days, warm evenings, and plenty of reasons to get out and explore—summer isn’t over yet in Middleburg! From the Sidewalk Sale to live music and community celebrations to winery events, and more, August is filled with opportunities to enjoy everything Middleburg has to offer. Take a look at what’s happening this month and start planning your next visit.
As always, be sure to visit our full Events Calendar for the latest updates. There is never a shortage of activity in our little corner of the world!
Middleburg’s 20th Annual Summer Sidewalk Sale!
The 20th Annual Summer Sidewalk Sale returns July 31 through August 2. Throughout the weekend, boutiques, galleries, specialty shops, and local businesses will bring their best bargains outdoors, offering incredible discounts on everything from fashion and home décor to gifts, artwork, and equestrian favorites. It’s the perfect opportunity to discover great deals from the businesses that make Middleburg unique.
Whether you’re searching for end-of-season savings, a one-of-a-kind treasure, or simply looking for a fun summer outing, the Summer Sidewalk Sale has something for everyone. Enjoy shopping at your own pace, stop into local restaurants and cafés for a bite to eat, and experience the welcoming atmosphere that has made this annual event a favorite for residents and visitors alike for two decades.
National Night Out is August 4th
Neighbors, friends, and families are invited to join the Middleburg Police Department for National Night Out 2026 on Tuesday, August 4, from 6:00 to 8:00 pm at the Middleburg Community Center Ballfield!
National Night Out is an annual tradition that brings the community together to strengthen relationships between residents and local law enforcement while celebrating the spirit that makes Middleburg such a special place to call home. The evening will include free food, snow cones, a moon bounce, a rock wall, giveaways, and plenty of opportunities to meet the officers who serve the community every day.
Bring the whole family, catch up with friends and neighbors, and enjoy a fun summer evening together at the Middleburg Community Center Ballfield, located at 300 W. Washington St., Middleburg, Va.
One town, one team, one community.
Second Annual Conservation Cup Golf Tournament
Tee off for a cause! Register today ready for the PFH Conservation Fund’s Conservation Cup Golf Tournament on Friday, August 14, 2026 at the Blue Ridge Shadows Golf Club in Front Royal!
8:00 am Check In
9:00 am Shotgun Start
Entry Fee: $125 per player or $500 per team of four
Sponsorships are Available
Join the fun to support PFHCF’S conservation efforts, protecting open countryside, wildlife habitat and our sporting traditions for future generations.
Questions? Contact Tournament Chairman Jerry Dabrowski at 703-309-9535 or dabrowsj@yahoo.com.
Click the button below for details and to register!
Slater Run Vineyards 10th Annual CrabFest
Slater Run Vineyards will host its annual CrabFest on the lawn, bringing the community together for an all-you-can-eat crab feast in support of the Churches of the Upperville Outreach Program!
The Outreach Program provides food and essential assistance to local families in need throughout the year. Around Thanksgiving, Christmas, Valentine’s Day, and Easter, volunteers deliver food parcels and holiday meals to families across the Upperville area, helping ensure neighbors have the support they need during the holiday seasons.
Funded through community donations, special holiday services, and local fundraising events like CrabFest, the program continues to make a meaningful difference in the lives of local families. Guests can enjoy a delicious meal while supporting a cause that strengthens the Upperville community.
Bryan Fox & Friends Concert at Middleburg Community Center
Pack a picnic, gather your family and friends, and head to the Middleburg Community Center Amphitheater for a relaxing summer evening of live music with one of the area’s favorite bands, Bryan Fox & Friends!
This free community concert is the perfect opportunity to spend time with neighbors while listening to great live music in the heart of Middleburg. Whether you’re a longtime local or visiting for the weekend, everyone is welcome to enjoy this fun and family-friendly evening.
Beer, wine, and other beverages will be available for purchase for guests ages 21 and older with a valid ID. Bring your picnic, your lawn chairs or blankets, and settle in for a memorable night of music, community, and summer fun!
Moonlight Zipline Tour at Salamander Middleburg
Experience the woods like never before with a full moon zipline adventure! Once a month, during the enchanting full moon, Salamander Adventures takes you into the treetops at night, where trained guides lead you through moonlit skies for a thrilling and unforgettable zipline tour.
Reservations are required. Ages 9 and up only.
For additional information or inquiries please call the Recreation Department 540-326-4060 or email recreation@salamanderresort.com.