Experience Middleburg

Middleburg and the surrounding Piedmont is home to some of the most unique activities and small businesses in the nation. Our established relationships with this hand selected list of local businesses will help you make the most of your time while staying with us. Read on to learn more about the many spectacular annual events and festivities that our region hosts, and please feel free to contact or visit our Inn Desk for additional advice and recommendations.

SPRING EVENTS

Historic Garden Week

Historic Garden Week

April 26-May 3, 2025
Historic Garden Week is the oldest and largest statewide house and garden tour event in the nation. Local tour is hosted by Fauquier and Loudoun Garden Club and the Leesburg Garden Club.

Middleburg Spring Races

Middleburg Spring Races

April 19, 2025
The quintessential event to welcome spring to Virginia.
36800 Glenwood Park Lane, Middleburg, VA 20117

Middleburg Spring Races

Virginia Gold Cup

May 3, 2025
The “Crown Jewel of American Steeplechasing.” Join us for the 99th Running of the Virginia Gold Cup.
Great Meadow
5089 Old Tavern Road, The Plains, VA 20198

Middleburg Spring Races

Art in the Burg

May 10, 2025
Celebrate the Arts with local vendors who sell homemade crafts and food – candles, jewelry, wearables, gourmet chocolates and nuts and more!
South Madison St. & Federal St., Middleburg, VA 20117

Middleburg Spring Races

DocWeek Middleburg Film Festival

May 13-17, 2025
One of the area’s most intriguing and enjoyable cultural events. Showing 5 films in 5 days.
300 W Washington St, Middleburg, VA 20117

Middleburg Spring Races

Hunt Country Stable Tour

May 24-25, 2025
A self driven tour of horse farms and facilities in Upperville, Middleburg and The Plains.
9108 John S Mosby Highway, Upperville, VA, 20184

SUMMER EVENTS

Twilight Polo

Twilight Polo

Starting in May 2025
Great Meadow
5089 Old Tavern Road, The Plains, VA 20198

Twilight Polo

Twilight Jumpers

Starting May 2024
Great Meadow
5089 Old Tavern Road, The Plains, VA 20198
540-253-9845

Buchanan Hall Farmers Market

Buchanan Hall Farmers Market

Wednesdays, 4:30-7:30PM · May 21 through September, 2025
Shop a collection of local produce, meat, dairy, bread, bagels, artisan items, and more!
8549 John S Mosby Hwy, Upperville, VA 20184

Buchanan Hall Farmers Market

Tarara Summer Concert Series

Saturdays, 6:00 PM · May 24 – September 27, 2025
Nineteen weeks of live music under the stars for the 25th year in a row!
Tarara Winery
13648 Tarara Lane, Leesburg, VA 20176

Buchanan Hall Farmers Market

Polo in the Park

Saturdays, 6:00-10:00PM · June  2025 
Get ready for the #BestPartyInLoudon with Polo in the Park, an exhilarating arena polo experience. Morven Park International Equestrian Center.
17195 Southern Planter Lane, Leesburg, VA 20176

Upperville Horse Show

The Upperville Colt & Horse Show

June 2-8, 2025
The Oldest Horse Show In The United States.
Grafton and Salem Showgrounds
8300 John S Mosby Hwy, Upperville, VA 20184

Upperville Horse Show

Middleburg Horse Trials

June 2025
Join us for our annual Middleburg Horse Trials to benefit the MOC Pony Club!
Great Meadow
5089 Old Tavern Road, The Plains, VA 20198

Upperville Horse Show

Fourth of July at Great Meadow

July 4, 2025
The 36th annual fireworks show from Great Meadow’s internationally acclaimed steeplechase course. The show begins at dusk, lasts 25 minutes, and is accompanied by a musical score.
Great Meadow
5089 Old Tavern Road, The Plains, VA 20198

Upperville Horse Show

Loudoun County Fair

July 22-26, 2025
Featuring live music, a demolition derby, a petting zoo and thrilling shows like the Gator Boys road show and the wild west showdown.
Loudoun County Fairgrounds
17558 Dry Mill Road, Leesburg, VA 20175

Great Meadow International

Virginia Scottish Games

August 30 – 31, 2025
High-performance eventing with numerous tailgating options, food trucks, and vendor village.
Great Meadow
5089 Old Tavern Road, The Plains, VA 20198

AUTUMN EVENTS

Great Meadow International

Middleburg Oktoberfest

September 20, 2025
Join us for Middleburg’s 5th Oktoberfest! Enjoy artwork from local artists, including fine art, pottery, jewelry, and more, available for purchase.
Middleburg
S. Madison and Federal Streets

Great Meadow International

NSLM Polo Classic

September 2025
Proceeds from this Polo Classic benefit the National Sporting Library & Museum in its mission to preserve, promote, and share the literature, art, and culture of equestrian, angling, and field sports as well as advocate for the conservation of open space and waterways crucial to these sports.
Great Meadow
5089 Old Tavern Road, The Plains, VA 20198

Great Meadow International

Piedmont Jumper Classic

September 2025
Enjoy the excitement of the competition amidst the beauty of Upperville. This event brings together top riders and horses, showcasing the skill and precision of show jumping in Virginia’s horse country.
Salem Showgrounds
8300 Little River Tpke, Upperville, VA 20184

Middleburg Spring Races

Virginia Fall Races

October 2025
Experience the annual fall tradition in the lovely Middleburg hunt country at The Virginia Fall Race.
36787 Glenwood Park Lane, Middleburg, VA, 20117

Middleburg Film Fest

Middleburg Film Festival

October 16-19, 2025
Four days of fantastic films in a spectacular setting.
Middleburg, Virginia

Middleburg Film Fest

1000 Miglia Warm Up

October 2025
Specialized training, competitive time trials, unique scenery and historic locations. All this in the fifth edition of the 1000 Miglia Warm Up USA 2025.
Middleburg, Virginia

Middleburg Film Fest

The Virginia Gold Cup Races

October 25, 2025
Celebrate the timeless tradition of steeplechase racing at the Virginia Gold Cup. Enjoy a thrilling day of competitive horse racing, tailgating, and fall festivities in the heart of Virginia’s countryside. Perfect for a day of outdoor fun and elegant gatherings.
Glenwood Park in Middleburg, Va

Cathy Zimmerman Art Exhibit

November 2025
Immerse yourself in vivid equestrian scenes & Virginia landscapes, open through December
11 W Washington St, Middleburg, VA 20117

Smithsonian Trees of North America

November 2025
Join an engaging conversation about the spectacular trees of North America
Oak Spring Garden Foundation
1776 Loughborough Lane, Upperville, VA 20184

Veteran’s Day

November 11, 2025
In honor of those who serve or have served, we’re offering a complimentary cocktail or dessert
2 E Washington St, Middleburg, VA 20117

Virginia Cider Week

November 2025
Celebrate local cider with tastings and events showcasing Virginia’s best blends
Virginia Cideries

5th Annual Celebrating the Harvest

November 2025
Join the Oak Spring Garden Foundation (OSGF) for a special evening as we gather around the table and celebrate the harvest through the seasons with a menu curated and created by Chef Jason Neve. Dishes will highlight a medley of heirloom crops grown at Oak Spring’s Biocultural Conservation Farm.
The Schoolhouse
8555 Mill Reef RoadMiddleburg, VA, 20117

Holiday Season Carriage Rides

November 2025
It’s going to be a Dickens of a Christmas in Middleburg!! Celebrate the season with a carriage ride through Town every weekend (except Parade Day, December 7) through December 29.
Middleburg, VA

Small Business Saturday

November 29, 2025
Shop over 100 unique boutiques in historic Middleburg for one of a kind holiday gifts
Middleburg, VA

WINTER EVENTS

Christmas in Middleburg

Christmas in Middleburg

December 6, 2025
A full day of family festival activities. One more marvelous way that this community comes together, celebrates a spiritually moving holy season, and individuates itself eccentrically and endearingly in doing so.

Christmas in Middleburg

Town of Middleburg Tree Lighting

December 5, 2025 
Gather with your friends, family and neighbors at The Middleburg Museum’s Pink Box for the Town of Middleburg Tree Lighting!
The Middleburg Museum
8 North Madison Street, Middleburg, VA 20117

Christmas in Middleburg

Jingle Jam Open Late Holiday Shopping

December 2025
Experience the magic of Middleburg this holiday season at Jingle Jam! Enjoy festive tunes, twinkling lights, and late-night shopping as you support local businesses in the most enchanting holiday town around.
Middleburg, VA

Christmas in Middleburg

A Dickens of a Christmas

December 13, 2025
Enjoy performances of A Christmas Carol, St. George and the Dragon, Holiday Vendors and Storytime at Middleburg Books. Bring your dancing shoes and groove with the Dickens Dancers!
Middleburg, VA
South Madison Street

Christmas in Middleburg

A Dickens of a Dog Parade

December 13, 2025
Dress your pup in festive holiday attire and join the fun at Middleburg’s Dickens of a Dog Parade, where furry friends and their humans can strut their stuff and win exciting prizes!
National Sporting Library & Museum
102 The Plains Rd, Middleburg, VA 20117

More Resources

Curious to learn more? You can also go to the Visit Middleburg and Visit Loudoun websites for more events and happenings in the area!