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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
April 2024

The Happiness of Color Spring Jewelry Event

The Byrne Gallery is pleased to present The Happiness of Color Spring Jewelry Event 2024. This special exhibition will feature jewelry and accessories for the new season by five local designers: Olga Chan, Debra Fabian, Margarita Smoroda, Kathryn Stanko and Susie Lipscher of Plum Blossom Kimono. Each of their one-of-a-kind collections incorporates color and compositions […]
Apr 06 - Jul 31
All Day
The Byrne Gallery
7 W Washington St, Middleburg, VA 20117

“Honoring the Point” The Gwynne McDevitt Sporting Dog Collection

Last spring, the National Sporting Library & Museum (NSLM) was the recipient of a generous bequest from Gwynne McDevitt. This illuminating sporting dog exhibition is comprised of 86 paintings, works on paper, sculptures, and a weathervane. The collection presents a range of dog breeds and subject matter: gun dogs in the field, foxhounds, canine portraits, […]
Apr 12 - Sep 15
All Day
National Sporting Library & Museum
102 The Plains Rd, Middleburg, VA 20117
May 2024

Champagne & Flowers 2024!

The Byrne Gallery is proud to present Champagne & Flowers 2024! an exhibition for the month of May by five talented local artists: Craig Arnold, Suzanne Lago Arthur, Caroline Hottenstein, Jeffrey Kibler and Carolyn Marshall Wright. Celebrating Flowers, Gardens and Spring, this exhibition will feature a range of artistic media. The artists will present works […]
May 01 - 31
All Day
The Byrne Gallery
7 W Washington St, Middleburg, VA 20117

Enter to Win Luke Combs Concert Tickets!

Become a New Member at Northwest Federal Credit Union to Enter for a chance to win two (2) suite tickets to the Luke Combs Concert at the Commanders Field on July 27th, 2024! Stop by the Middleburg Branch at 101 W. Washington St. for additional details. Call 703-925-5037 to schedule an appointment with a member […]
May 13 - Jul 20
All Day
Northwest Federal Credit Union
101 West Washington Street, Middleburg, VA 20117

Middleburg Farmer’s Market

The Middleburg Farmers Market season begins on Saturday, May 4th at the Middleburg Town Hall. The Middleburg Farmers Market is sponsored by the Town of Middleburg to provide local agriculturalists with a retail outlet for their products. The market provides the citizens of the area with an opportunity to purchase fresh quality products from the […]
May 25
9:00 am - 12:00 pm
Middleburg Town Hall
10 West Marshall Street, Middleburg, VA 20117

65th Hunt Country Stable Tour

Make your plans now for Memorial Day Weekend and partake in the 65th Annual Hunt Country Stable Tour, a weekend filled with equestrian elegance, rural charm, and the timeless beauty of Hunt Country! Whether you’re a seasoned rider, a horse enthusiast, or simply captivated by the grace of these magnificent animals, this event promises something […]
May 25
10:00 am - 4:00 pm
Trinity Episcopal Church
9108 John S. Mosby Hwy, Upperville, VA 20184

Art Show to Celebrate 100th Anniversary of the Old Dominion Hounds

Art sale of paintings and bronze sculptures. A benefit for the Old Dominion Hounds. Proceeds from sale to suport the Old Dominion Educational and Environmental Foundation and the Musuem of Hounds and Hunting North America for Museum Members and their guests. Secure tickets in person at the Musuem at 11 W. Washington Street or online!
May 25
11:00 am - 4:00 pm
Museum of Hounds & Hunting
11 West Washington Street, Middleburg, VA 20117

Art Show to Celebrate 100th Anniversary of the Old Dominion Hounds

Art sale of paintings and bronze sculptures. A benefit for the Old Dominion Hounds. Proceeds from sale to suport the Old Dominion Educational and Environmental Foundation and the Musuem of Hounds and Hunting North America for Museum Members and their guests. Secure tickets in person at the Musuem at 11 W. Washington Street or online!
May 26
11:00 am - 4:00 pm
Museum of Hounds & Hunting
11 West Washington Street, Middleburg, VA 20117
people at library sketching

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 […]
May 26
2:30 pm - 4:00 pm
National Sporting Library & Museum
102 The Plains Rd, Middleburg, VA 20117

Buchanan Hall Farmer’s Market

The Buchanan Hall Farmer’s Market is back for the 2024 season! Every Wednesday at The Hall on Route 50 in Upperville, shop a collection of local produce, meat, dairy, bread, bagels, artisan items and more! The third Wednesday of the month is the BIG BAZAAR Day, when the Market will host additional artisan and boutique […]
May 29
4:30 pm - 7:30 pm
Buchanan Hall
8549 John S. Mosby Hwy. Upperville, VA 20184

Middleburg Day

Middleburg Day will celebrate the joy and connection of our community – consider it a community picnic – with great food, music, games, and community spirit. Food will be provided by the Town! This space provides ample room to set out a picnic blanket, toss a frisbee, gather with friends, listen to music and enjoy […]
May 31
5:00 am - 7:00 pm
Middleburg Town Hall
10 West Marshall Street, Middleburg, VA 20117

Hunt Country Inspired Designer Decoupage Plates Event

Original Designer Decoupage Plates exclusively at The Museum of Hounds and Hunting. The gorgeous designer silk scarves by Hermes, Gucci, Versace, and Cartier inspired the decoupage plate collection. In this French decorating technique fragments of the material, in this case cut-up scarves and high-end fabrics, are sealed between layers of varnishes with repeated applications to […]
May 31 - Jun 02
11:00 am - 4:00 pm
June 2024

Jack Boul: Timeless Landscapes

Since 1951, Jack Boul (American, b. 1927) has lived and worked in the Washington, DC, area. He found inspiration for his artwork in the now-disappearing Virginia and Maryland countryside. The artist painted en plein air for much of his career and then in his studio from reference photographs. Classically trained, Boul attended American Artist’s School […]
Jun 01 - Jan 12
All Day
National Sporting Library & Museum
102 The Plains Rd, Middleburg, VA 20117

“Shenandoah Summer” Exhibit

The Byrne Gallery exhibition for June showcases the iconic views of the Shenandoah Valley that everyone loves to come and enjoy. Gerald Hennesy, the Gallery’s signature artist for Plein Air landscape, is widely collected and loved; the gallery is pleased to add a new artist, Katie Flack, who was chosen Best New Plein Air Artist […]
Jun 01 - 30
All Day
The Byrne Gallery
7 W Washington St, Middleburg, VA 20117

Middleburg Farmer’s Market

The Middleburg Farmers Market season begins on Saturday, May 4th at the Middleburg Town Hall. The Middleburg Farmers Market is sponsored by the Town of Middleburg to provide local agriculturalists with a retail outlet for their products. The market provides the citizens of the area with an opportunity to purchase fresh quality products from the […]
Jun 01
9:00 am - 12:00 pm
Middleburg Town Hall
10 West Marshall Street, Middleburg, VA 20117

Vintage Market

Visit Lost Barrel Brewing in Middleburg for a day of vintage shopping, music, beverages, food and good friends! Support local small business while hunting for your treasures. Our desire is to bring together the community in a joy-filled day of shopping, music and good friends! Enjoy the hunt and support sustainability. Whether you’re a vintage […]
Jun 01
11:00 am - 4:00 pm
Lost Barrel Brewing
36138 John Mosby Hwy, Middleburg, VA 20117

Enneagram Basics

Learn about this personality assessment tool and discover which of the nine personality types you most align. Presented by Enneagram life coach and author DeeAnn Jeremiah. Brought to you by the Middleburg Library Advisory Board.
Jun 01
2:00 pm - 3:00 pm
Middleburg Library
101 Reed St, Middleburg, VA 20117

First Friday

You’re invited to Greenhill’s historic Manor House in the heart of quintessential Virginia Wine Country. Enjoy dinner from either food truck, Talk of the Mountain Seafood or Arepa Vibes, and live music from Will Shepard, while sipping on your favorite Greenhill wine! Because seating is limited, we are not taking reservations; however, we ask that […]
Jun 01
5:00 pm - 8:00 pm
Greenhill Winery
23595 Winery Ln, Middleburg, VA

Upperville Jump4Fun

Upperville Jump4Fun returns to the iconic showgrounds on June 2, 2024 and offers a fantastic opportunity to compete over professionally designed courses on world-class footing. This day of unrecognized showing is a great way for horses and riders to gain experience and have fun! Click here for the Prize List.
Jun 02
All Day
Upperville Colt & Horse Show
8300 John S. Mosby Hwy., Upperville, VA 20184

Rodney Jenkins: The Red Rider Project

A timely, major archival donation set into motion Rodney Jenkins: The Red Rider Project, an interactive exhibit that chronicles the life and achievements of show jumping’s winningest figure. Come and add to the larger conversation about Jenkins’ impact on the horse world. Library will be open every day during the first week of June. Join […]
Jun 03 - 09
12:00 pm - 4:00 pm
National Sporting Library & Museum
102 The Plains Rd, Middleburg, VA 20117

Community Paint Club

Do you love to paint, but don’t have a regular time and place to indulge your artistic pursuits? Perhaps you find yourself surrounded by unfinished canvases and are seeking some guidance and direction. Or are you new to painting and eager to learn, but unable to commit to a weekly class? Paint Club was designed […]
Jun 04
10:00 am - 1:00 pm
The Artists in Middleburg
102 W Washington St, Middleburg, VA 20117

Middleburg Books Speculative Fiction Book Club

Welcome to Middleburg Books’ Speculative Fiction Book Club! We’re thrilled to host readers at our jewel-box of a shop as we discuss a plethora of new fiction. Our novel for June is A Marvellous Light by Freya Marske, featuring an Edwardian England full of magic, contracts, and conspiracies. Click here to RSVP.
Jun 04
6:00 pm - 7:00 pm
Middleburg Books
17 South Madison Street, Middleburg, Virginia, 20117

Buchanan Hall Farmer’s Market

The Buchanan Hall Farmer’s Market is back for the 2024 season! Every Wednesday at The Hall on Route 50 in Upperville, shop a collection of local produce, meat, dairy, bread, bagels, artisan items and more! The third Wednesday of the month is the BIG BAZAAR Day, when the Market will host additional artisan and boutique […]
Jun 05
4:30 pm - 7:30 pm
Buchanan Hall
8549 John S. Mosby Hwy. Upperville, VA 20184

$25,000 Upperville USHJA International Hunter Derby

Join the excitement, tradition and pageantry of the $25,000 Upperville USHJA International Hunter Derby “Under the Oaks” on Thursday, June 6, 2024. The USHJA International Hunter Derby is a program designed to bring tradition and art of horsemanship back to the show ring. The hunter derby class aims to bring more athleticism, bravery, and brilliance […]
Jun 06
4:00 pm - 6:00 pm
Upperville Colt & Horse Show
8300 John S. Mosby Hwy., Upperville, VA 20184

Middleburg Books Presents John Ross

Join Middleburg Books on D-Day in Middleburg for a reading and signing with John Ross, featuring his novel, The Forecast for D-Day. The author will read an excerpt and participate in a Q&A which will be followed by a signing at the bookshop. Snacks and beverages will be served. Click here to RSVP.
Jun 06
5:30 pm - 7:00 pm
Middleburg Books
17 South Madison Street, Middleburg, Virginia, 20117

Hunt Country Inspired Designer Decoupage Plates Event

Original Designer Decoupage Plates exclusively at The Museum of Hounds and Hunting. The gorgeous designer silk scarves by Hermes, Gucci, Versace, and Cartier inspired the decoupage plate collection. In this French decorating technique fragments of the material, in this case cut-up scarves and high-end fabrics, are sealed between layers of varnishes with repeated applications to […]
Jun 07 - 09
11:00 am - 4:00 pm

Middleburg Farmer’s Market

The Middleburg Farmers Market season begins on Saturday, May 4th at the Middleburg Town Hall. The Middleburg Farmers Market is sponsored by the Town of Middleburg to provide local agriculturalists with a retail outlet for their products. The market provides the citizens of the area with an opportunity to purchase fresh quality products from the […]
Jun 08
9:00 am - 12:00 pm
Middleburg Town Hall
10 West Marshall Street, Middleburg, VA 20117

$226,000 FEI4* Upperville Jumper Classic

Celebrate the Nation’s Oldest Horse Show June 3-9, 2024 in Upperville, Virginia! The week-long show culminates on June 9 with the excitement of the $226,000 Upperville Jumper Classic CSI4* featuring top world-class equestrians. The day’s entertainment includes junior and amateur riders, a hat contest and the Horses & Horsepower car show. Vendors throughout the show […]
Jun 09
3:00 am - 6:00 pm
Upperville Colt & Horse Show
8300 John S. Mosby Hwy., Upperville, VA 20184

Paws, Brushes & Pet Portraiture Class

Join artist Heather Connole in our pet portraiture class, where you’ll learn to translate the unique essence of your beloved companion onto canvas. Heather will guide you through the process, helping you choose your preferred medium and unraveling techniques to accentuate every detail of your pet’s features. With personalized instruction and step-by-step guidance, you’ll develop […]
Jun 11
10:00 am - 2:00 pm
The Artists in Middleburg
102 W Washington St, Middleburg, VA 20117

Loudoun Benefit Horse Show

The Loudoun Benefit Horse Show began in 1951, running as a Junior and Pony Show for several decades. Held for many years at Glenwood Park in Middleburg it was among the many prestigious stops along the Virginia show circuit. Today’s show is held at the Upperville Show Grounds on Route 50, the week following the […]
Jun 12 - 16
All Day
Loudoun Benefit Horse Show
8300 John S. Mosby Hwy., Upperville, VA 20184

Buchanan Hall Farmer’s Market

The Buchanan Hall Farmer’s Market is back for the 2024 season! Every Wednesday at The Hall on Route 50 in Upperville, shop a collection of local produce, meat, dairy, bread, bagels, artisan items and more! The third Wednesday of the month is the BIG BAZAAR Day, when the Market will host additional artisan and boutique […]
Jun 12
4:30 pm - 7:30 pm
Buchanan Hall
8549 John S. Mosby Hwy. Upperville, VA 20184

Author Event with Brian J. Morra

Join the fun in Middleburg for a reading and signing with Brian J. Morra, featuring his new novel, The Righteous Arrows. The author will read an excerpt and participate in a Q&A which will be followed by a signing at the bookshop. Snacks and beverages will be served. Click here to RSVP!
Jun 12
5:00 pm - 7:00 pm
Middleburg Books
17 South Madison Street, Middleburg, Virginia, 20117

Oak Spring Garden Tour: Explore Bunny Mellon’s Legacy

In case you missed Historic Garden Week, or perhaps you just want to come back and see the gardens in a new state this June! The Oak Spring Garden Foundation is a legacy of the designer, horticulturist and philanthropist Rachel Lambert “Bunny” Mellon. Mrs. Mellon’s hope was that her extensive collection of rare books, artwork, […]
Jun 14
9:00 am - 4:00 pm
Oak Spring Garden Foundation
1776 Loughborough Lane, Upperville, VA 20184

Hunt Country Inspired Designer Decoupage Plates Event

Original Designer Decoupage Plates exclusively at The Museum of Hounds and Hunting. The gorgeous designer silk scarves by Hermes, Gucci, Versace, and Cartier inspired the decoupage plate collection. In this French decorating technique fragments of the material, in this case cut-up scarves and high-end fabrics, are sealed between layers of varnishes with repeated applications to […]
Jun 14 - 16
11:00 am - 4:00 pm

Middleburg Farmer’s Market

The Middleburg Farmers Market season begins on Saturday, May 4th at the Middleburg Town Hall. The Middleburg Farmers Market is sponsored by the Town of Middleburg to provide local agriculturalists with a retail outlet for their products. The market provides the citizens of the area with an opportunity to purchase fresh quality products from the […]
Jun 15
9:00 am - 12:00 pm
Middleburg Town Hall
10 West Marshall Street, Middleburg, VA 20117

Oak Spring Garden Tour: Explore Bunny Mellon’s Legacy

In case you missed Historic Garden Week, or perhaps you just want to come back and see the gardens in a new state this June! The Oak Spring Garden Foundation is a legacy of the designer, horticulturist and philanthropist Rachel Lambert “Bunny” Mellon. Mrs. Mellon’s hope was that her extensive collection of rare books, artwork, […]
Jun 15
9:00 am - 4:00 pm
Oak Spring Garden Foundation
1776 Loughborough Lane, Upperville, VA 20184

Summer Bouquet Workshop with C&S Farmstead

Join Slater Run Vineyards for an evening at the winery creating your own summer bouquet masterpiece under the guidance of local floral design master and grower, Sharla Bond of C&S Farmstead (flowers and vase included). Attendees are welcome to enjoy Slater Run’s club member night featuring live music by Boo Snider and dinner by Sexi […]
Jun 15
6:00 pm - 9:00 pm
Slater Run Vineyards
1500 Crenshaw Rd, Upperville, VA 20184

Lost Barrel Brewing Father’s Day Brunch

Join Lost Barrel Brewing for Father’s Day Brunch for live music, delicious food and drinks! We will have our full food and drink menu and some fun special brunch items. Our menu is a la carte, there is no charge to visit LBB on Father’s Day. Our full menu is available in any space that […]
Jun 16
11:00 am - 7:00 pm
Lost Barrel Brewing
36138 John Mosby Hwy, Middleburg, VA 20117

Father’s Day BBQ

Treat Dad to lunch and an upscale BBQ buffet catered by Monk’s BBQ live music in our Pavilion overlooking the lush vineyard and winery. slow-cooked, smoked meats using the best elements of the Carolinas, Texas, Memphis and Kansas City style BBQ Cornbread, Mac & smoked gouda cheese, and collard greens, plus dessert Music by Rook […]
Jun 16
11:30 am - 2:30 pm
Boxwood Estate Winery
2042 Burrland Ln, Middleburg, VA 20117

Fiction Book Club

Welcome to Middleburg Books’ Literary Fiction Book Club! We’re thrilled to host readers at our jewel-box of a shop as we discuss a plethora of new fiction. Our novel for June is James by Percival Everett, a brilliant, action-packed reimagining of The Adventures of Huckleberry Finn, both harrowing and ferociously funny, told from James’ point-of-view. […]
Jun 18
6:00 pm - 7:00 pm
Middleburg Books
17 South Madison Street, Middleburg, Virginia, 20117

Juneteenth Celebration

In honor of Juneteenth, Wendy Osborn and Chloe’s of Middleburg are hosting an afternoon of shopping followed by a specialty wine-pairing dinner at The Piedmont Club. Chef Pete Smith, in collaboration with Kindra Dionne of The Fifty Leven Collection, will curate a locally sourced menu paired harmoniously with fine wines, promising a delightful culinary experience. […]

Buchanan Hall Farmer’s Market

The Buchanan Hall Farmer’s Market is back for the 2024 season! Every Wednesday at The Hall on Route 50 in Upperville, shop a collection of local produce, meat, dairy, bread, bagels, artisan items and more! The third Wednesday of the month is the BIG BAZAAR Day, when the Market will host additional artisan and boutique […]
Jun 19
4:30 pm - 7:30 pm
Buchanan Hall
8549 John S. Mosby Hwy. Upperville, VA 20184

Hunt Country Inspired Designer Decoupage Plates Event

Original Designer Decoupage Plates exclusively at The Museum of Hounds and Hunting. The gorgeous designer silk scarves by Hermes, Gucci, Versace, and Cartier inspired the decoupage plate collection. In this French decorating technique fragments of the material, in this case cut-up scarves and high-end fabrics, are sealed between layers of varnishes with repeated applications to […]
Jun 21 - 23
11:00 am - 4:00 pm

Middleburg Farmer’s Market

The Middleburg Farmers Market season begins on Saturday, May 4th at the Middleburg Town Hall. The Middleburg Farmers Market is sponsored by the Town of Middleburg to provide local agriculturalists with a retail outlet for their products. The market provides the citizens of the area with an opportunity to purchase fresh quality products from the […]
Jun 22
9:00 am - 12:00 pm
Middleburg Town Hall
10 West Marshall Street, Middleburg, VA 20117
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