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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
May 2026

“The Animal in Art: Highlight the Horse, Fox and Hound” Exhibit

The Artists in Middleburg annual Animals in Art: Highlighting the Horse, Fox and Hound exhibition celebrates the beauty, spirit, and tradition of the horse, fox, and hound. This show honors the animals that are central to our region’s landscape and heritage. It represents 50 local artists with all new work.
May 09 - Jun 14
All Day
The Artists in Middleburg
102 W Washington St, Middleburg, VA 20117
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June 2026

Fourth Annual Feast in the Field at Oak Spring Garden Foundation

The Oak Spring Garden Foundation invites you to an evening at the Biocultural Conservation Farm to welcome the summer season. Enjoy a stroll through the vegetable fields with light bites, refreshments, and a summer-inspired cocktail, followed by a family-style dinner by Chef Jason Neve featuring crops grown on-site. Proceeds support OSGF’s Education and Outreach programs. […]
Jun 05
5:30 pm - 8:30 pm
Oak Spring Garden Foundation Walled Garden
8616 Mill Reef Road, Upperville, VA 20184
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Beer Release: Cream Ale

Join Lost Barrel Brewing for the release of its latest brew, a bright and refreshing Cream Ale. Smooth, crisp, and easy to drink, this new addition balances light malt sweetness with a clean, refreshing finish. It is crafted for warm days, relaxed afternoons, and anyone who enjoys a beer that goes down effortlessly.
Jun 11
12:00 pm - 8:00 pm
Lost Barrel Brewing
36138 John Mosby Hwy, Middleburg, VA 20117
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Inaugural Crémant Release Party

Celebrate history, craftsmanship, and bubbles at Boxwood Estate Winery’s Inaugural Crémant Release Party. Join Boxwood Estate Winery in the pavilion for an unforgettable afternoon marking three milestones: 20 years of Boxwood Estate Winery, 200 years of Boxwood Farm, and 250 years of our country. Be there as our winemaker, Steven Rigby, pops the very first […]
Jun 11
1:00 pm - 4:00 pm
Boxwood Estate Winery
2042 Burrland Ln, Middleburg, VA 20117
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“The Gardens of Bunny Mellon” with Author Linda Jane Holden

Join NSLM for an evening that includes a cocktail reception followed by an author discussion, Q&A, and book signing. Linda Jane Holden will discuss her book, The Gardens of Bunny Mellon, which celebrates the life and work of renowned garden designer Rachel “Bunny” Mellon, featuring her private gardens at estates like Oak Spring and public […]
Jun 11
5:00 pm - 7:00 pm
National Sporting Library & Museum
102 The Plains Rd, Middleburg, VA 20117
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Garden Dialogues

Discover three exceptional, rural retreats, where the pastoral landscape of the greater Washington, D.C., metropolitan area—historically farmland—meets innovative, modern design in Leesburg, VA. Curated by Jennifer Horn, founding Principal of Jennifer Horn & Company, this exclusive tour stops at three separate sites, each designed by a different, leading D.C.-based firm, including Moody Graham Landscape Architecture […]
Jun 13
11:00 am - 2:00 pm
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Imagine Life Coaching Middleburg Retreat

Imagine Life Coaching invites you to a restorative day focused on reflection, renewal, and personal alignment. This gathering at 22865 Foxcroft Rd offers a peaceful setting for connection and growth. Through mindful practices, creative exploration, and time in nature, attendees will support their well‑being during this season of transition. The day includes an Enneagram discovery […]
Jun 14
9:00 am - 3:30 pm
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