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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
October 2026

“Harvest: Celebrating Gatherings and Memories” Exhibit

The Byrne Gallery in Middleburg proudly presents Harvest: Celebrating Gatherings and Memories, a new exhibition in the month of October. This month, artist Sandra Iafrate will depict the beauty of the harvest season and the enduring connections between food, memory, family, and place. Iafrate’s use of collected materials and paint instills memories of gathering from […]
Oct 02 - Nov 01
All Day
The Byrne Gallery
7 W Washington St, Middleburg, VA 20117
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Movie Night: Alfred Hitchcock’s “Notorious”

Join Middleburg Library for an Alfred Hitchcock movie every Wednesday night in October. Refreshments are provided. Watch Notorious (TV-PG, 101 minutes). A romantic thriller about a government agent (Cary Grant) trying to gather evidence on a suspected Nazi gang in Brazil. He recruits Alicia Huberman (Ingrid Bergman), who agrees to marry the gang’s leader (Claude […]
Oct 21
6:00 pm - 8:00 pm
Middleburg Library
101 Reed St, Middleburg, VA 20117
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Foxcroft School Family Weekend

The Foxcroft School is looking forward to hosting families during Family Weekend 2025! Between visiting classes, cheering for FXC during the athletic competitions, enjoying the Parents’ Association’s FamilyFest and raffle, and having individual appointments with teachers, parents will get a firsthand look at their daughters’ lives at Foxcroft.
Oct 23 - 24
All Day
Foxcroft School
22407 Foxhound Lane Middleburg VA
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Cathy Zimmerman Art Exhibition, Reception & Sale

An Evening with the Artist Art Exhibition & Sale | The Hill School | Sheila Johnson Performing Arts Center | October 23–25 Some of life’s greatest journeys begin with a teacher who recognizes potential before a child recognizes it in themselves. For acclaimed Hunt Country artist Cathy Zimmerman, that journey began at The Hill School […]
Oct 23 - 25
All Day
The Hill School
130 South Madison Street, Middleburg, VA 20117
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50th Anniversary of Emmanuel Episcopal Church’s Reiger Organ

Celebrate the 50th anniversary of Emmanuel Episcopal Church’s Reiger organ. Playing will be local musicians including Jim Moon from St. James Leesburg, Marilyn Shenenberger from Winchester, Dan Miller formerly of Trinity Upperville, and Emmanuel music director Emily Mason. The event is free and open to the public. More information is here or call 540-687-6297 or […]
Oct 23
7:00 pm - 8:00 pm
Emmanuel Episcopal Church
105 East Washington Street, Middleburg, VA 20117
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Sprout 5K

The Sprout 5K supports Sprout Therapeutic Riding & Education Center in Aldie, Virginia—a nonprofit (501(c)(3)) dedicated to changing lives through partnerships with horses. Sprout provides high-quality, adaptive programming that supports the physical, cognitive, social, and emotional development of individuals with a wide range of diagnoses. Each week, Sprout serves more than 185 individuals, made possible […]
Oct 25
All Day
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Sunday Sketch

Held the last Sunday of every month. Participation in the program is free and open to the public: no sign-up is required, and all necessary materials are provided. Visitors may also enjoy free admission to the Museum on these days, regardless of participation in the program. The NSLM reserves the right to cancel or reschedule […]
Oct 25
2:00 pm - 4:00 pm
National Sporting Library & Museum
102 The Plains Rd, Middleburg, VA 20117
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Halloween Songs & Stories

All Hallow’s Eve is creeping up on us. Give your costume a test run at the Seventh Annual “Halloween Songs & Stories”! Join ghouls, goblins, superheroes, unicorns, you name it, for Halloween silliness, fun songs and spooky stories (Headless Horseman, “Monster Mash,” and so much more). Everyone in costume gets a bag of Halloween treats […]
Oct 25
3:00 pm - 4:30 pm
Emmanuel Parish House
105 E Washington St, Middleburg, VA 20117
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Movie Night: Alfred Hitchcock’s “The Birds”

Join Middleburg Library for an Alfred Hitchcock movie every Wednesday night in October. Refreshments are provided. Watch The Birds (PG-13, 120 minutes). An avian attack on a California coastal town, where fierce birds descend upon a chicken farmer, a schoolyard full of children, and a socialite.  
Oct 28
6:00 pm - 8:00 pm
Middleburg Library
101 Reed St, Middleburg, VA 20117
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Hot Dog: It’s Halloween!

Hot Dog, It’s Halloween! Calling all ghosts, goblins, and hungry little monsters! Join us for this favorite Middleburg tradition on October 31 at 5 PM at the Middleburg Community Center. Put on your costumes, round up your crew, and come enjoy hot dogs and Halloween fun with friends and neighbors. It’s a FREE family event […]
Oct 31
5:00 pm - 7:00 pm
Middleburg Community Center
300 W Washington St, Middleburg, VA 20117
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