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Local Events in Middleburg

Come & Join the Fun!

Renowned as the Nation’s Horse & Hunt Capital, Middleburg offers a variety of equestrian events throughout the year, including the Middleburg Spring Races and the Virginia Fall Races. It’s also a well-known destination for the arts with events like the Middleburg Film Festival and Art in the Burg.

Christmas in Middleburg draws thousands of visitors, who line the streets on the first Saturday in December to watch the parade and the Middleburg Hunt Revue.

Check the calendar below to find out what’s happening around town.

Audience in lawn chairs clapping in front of National Sporting Library and Museum
September 2026

“Horizons: Where Earth Meets Sky” Exhibit

The Byrne Gallery proudly presents Horizons: Where Earth Meets Sky, the new exhibition for the month of September. Local artists Laura Bollettino, Katie Flack, and Gerald Hennesy will explore the timeless beauty of the landscape and the quiet wonder found where land and sky converge. Through scenes of coastlines, fields, marshes, and mountains, the exhibition […]
Sep 02 - 27
All Day
The Byrne Gallery
7 W Washington St, Middleburg, VA 20117
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Caroline Jean Gray Exhibit at the Castle Gallery

Join Caroline Jean Gray Photography for a fine art photography pop-up at Castle Gallery featuring her conservation artwork featuring scenes from Hunt Country, Nantucket, and the wild horses in Utah. Proceeds go to support the Piedmont Environmental Council, Nantucket Conservation Foundation, and Saving Gracie’s Healing Equine Foundation.
Sep 04
11:00 am - 5:00 pm
Castle Gallery
10 East Federal Street, Middleburg, Va 20117
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“A Midsummer Night’s Dream” at Middleburg Community Center

Jupiter Theater Company brings Shakespeare’s beloved comedy outdoors at Middleburg Community Center! When unlucky lovers, feuding fairies and an earnest troupe of amateur actors collide in an enchanted Athenian forest, romance, mischief, illusion and laughter follow. Bring a picnic blanket or lawn chairs and enjoy an evening of classical theater under the open sky. Snacks, […]
Sep 05
5:00 pm - 7:00 pm
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“A Midsummer Night’s Dream” at Middleburg Community Center

Jupiter Theater Company brings Shakespeare’s beloved comedy outdoors at Middleburg Community Center! When unlucky lovers, feuding fairies and an earnest troupe of amateur actors collide in an enchanted Athenian forest, romance, mischief, illusion and laughter follow. Bring a picnic blanket or lawn chairs and enjoy an evening of classical theater under the open sky. Snacks, […]
Sep 06
5:00 pm - 7:00 pm
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Revive Clinic and IV Therapy Grand Opening and Ribbon Cutting

Revive Clinic and IV Therapy Med Spa & Wellness Center is opening its doors for an exciting Open House and Ribbon Cutting! Come celebrate this new addition to the community, tour the space, meet the team, and discover all that Revive has to offer. Join in the celebration and be among the first to experience […]
Sep 10
3:00 pm - 7:00 pm
Revive Clinic and IV Therapy
200 East Washington Street, Middleburg, VA 20117
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9/11 Remembrance Ceremony

Join the Town of Middleburg and gather to remember and honor the lives lost on September 11, 2001. On the 25th anniversary of 9/11, our community will come together in reflection, remembrance, and gratitude for the courage and service shown that day and in the years since. The ceremony will take place at Town Hall, […]
Sep 11
5:00 pm - 6:00 pm
Middleburg Town Hall
10 West Marshall Street, Middleburg, VA 20117
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Granted Wellbeing Grand Opening

Middleburg’s newest destination for self-care is celebrating its grand opening, and everyone is invited to come see what Granted Wellbeing is all about! Stop by for tours of the center, indulgent treats to sample, giveaways throughout the day, and a first look at the treatments and infrared sauna experiences designed to nourish mind and body. […]
Sep 12
11:00 am - 5:00 pm
Granted Wellbeing
11 South Madison Street, Middleburg, VA 20117
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Bridgerton Wine Tasting

Dearest gentle reader, Please join Boxwood Estate Winery for an afternoon most divine amidst the verdant splendor of our vineyard, where the vines themselves seem to whisper secrets of romance and revelry. Come promenade through the rows, flights of wine in hand, as the golden sun casts its gentle glow upon the gathering. Do ready […]
Sep 12
1:00 pm - 4:00 pm
Boxwood Estate Winery
2042 Burrland Ln, Middleburg, VA 20117
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2026 Gallop Gala

The Sprout Gala is Sprout Therapeutic Riding & Education Center’s annual celebration of service. This black-tie event begins with valet parking upon your arrival and includes an elegant cocktail hour with signature drinks, a delicious dinner and a robust silent and live auctions. Guests have the opportunity to tour the barn, meet the horses and […]
Sep 12
6:00 pm - 10:00 pm
Sprout Therapeutic Riding & Education Center
40685 Little River Turnpike Aldie, VA 20105
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