Town of Middleburg, VA

HEALth Expo & 5K - Spring Event - Learn about Healthy Eating, Active Living! Free health screenings, classes, healthy eating options, presentations.  Compete in the HEALTHY PASSPORT TREASURE HUNT for the chance to receive gifts and win prizes!  Local food, health & fitness vendors.

SUMMER SIDEWALK SALE - First weekend in August (Friday, Saturday & Sunday) - The Middleburg Business & Professional Association hosts an annual Summer Sidewalk Sale each year to coincide with the Virginia Tax Relief Weekend.  Look for the red balloons at participating local businesses!

SPECIAL EVENTS

SHAKESPEARE IN THE BURG - Held in the spring, this festival brings the plays of William Shakespeare alive in our bucolic countryside.  Workshops in stagecraft and acting are also avialable, as well as a one-act playwriting competition with public readings/performances of the winners.

FALL ART IN THE BURG -  Annually the 3rd Saturday in September - Join the Middleburg Arts Council during their biannual celebration, featuring artwork from more than 20 local and regional artists.  Art lovers will get the opportunity to purchase original works without gallery fees.  While you're here, visit Middleburg's many restaurants and quaint shops.  Held on South Madison Street.

MIDDLEBURG FILM FESTIVAL - Fall Event - Four days of fantastic films in a spectacular setting!  Films include festival favorites, world premiers, first-class foreign films and Academy Award Contenders.  

FOURTH OF JULY CELEBRATION - Middleburg Community Center

CHRISTMAS IN MIDDLEBURG - 1st Saturday in December - Rain or Shine.  A Christmas experience like no other!  Featuring the Middleburg Hunt Review, Christmas Parade, Breakfast with Santa, Craft Fair, Spirits of Middleburg and much more.  Also, don't miss the Annual Christmas Tree Lighting Ceremony is held the Friday evening before Christmas in Middleburg!

Winter Sidewalk Sale - The Middleburg Business & Professional Association plays host to an annual Winter Sidewalk Sale held during the Presidents Day weekend in February (Friday, Saturday & Sunday).  Look for the red balloons at local businesses who participate in this event.  Find wonderful items at great prices!  

Middleburg is the home to a variety of special events and activities.  We invite you to join us for.....


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National Night Out - Annually first Tuesday in August - Join the Middleburg Police Department in their annual community-building campaign to promote strong police-community partnerships and build neighborhood camaraderie.  Rock climbing wall, bounce house, dunk tank, free food and beverages and more!!!

SPRING ART IN THE BURG - Join the Middleburg Arts Council during their biannual celebration, featuring artwork from more than 20 local and regional artists.  Art lovers will get the opportunity to purchase original works without gallery fees.  While you're here, visit Middleburg's many restaurants and quaint shops.  Held on South Madison Street.

Middleburg Hunt Point-to-Point - Annually the last Saturday in April at Glenwood Park - Enjoy the exciting sport of steeplechase racing at one of the most beautiful race courses in the nation! 

Photo courtesy:  Visit Loudoun/Joy Asico/Asico Photo

Photo:  Upperville Horse Show

VIRGINIA FALL RACES - Second Saturday in October @ Glenwood Park - Experience the annual fall tradition in MIddleburg's hunt country. Watch steeplechase action at the oldest continuous race course in Virginia. 

Upperville Horse Show - Annually the first full week in June - More than a horse show - a fixture on the equestrian calendar!  The oldest horse show in America, featuring the nation's top ranking hunters and jumpers competing alongside local ponnies, sidesaddle ladies and racing Jack Russell Terriers.  

MIDDLEBURG SPRING RACES -  Annually the 3rd Saturday In April at Glenwood Park - Virginia's oldest steeplechase!  Come see the nation's most athletic thoroughbreds compete at high speeds over hedges and timbers.  Tailgating at its best!