Annual Events

Loudoun is home to many annual events that attract visitors from all over the country. Experience regional culinary offerings, enjoy the beautiful backdrop of the Blue Ridge Mountains and learn more about Loudoun’s history and culture that is celebrated throughout our towns and villages.

Be sure to check our events calendar for updated dates and information!

• Leesburg Flower & Garden Festival – April. Fragrant spring flower show in downtown Leesburg featuring floral designers, landscapers, garden suppliers and vendors.
• Hillsboro Gardens in the Gap – April.  Arts, crafts, native plants, public speakers, live music and more at this festival in the Old Stone School.
• Middleburg Spring Races – April. Glenwood Park hosts this premier steeplechase event that attracts race aficionados and designer clad socialites.
• Spring Farm Tours – May. Visit some 40 Loudoun farms, meet local families, pet farm animals and buy incredible fresh produce on this annual spring tour.
• Western Loudoun Artists Studio Tour – June. Visit and buy work from painters, potters, photographers, fiber artists and artisans living and working in Western Loudoun.
• Purcellville Wine and Food Festival – July. Day-long summer festival at Fireman’s Field where local wineries, breweries, restaurants and food trucks sell tasty treats.
• Loudoun County Fair – July/August. Annual summer fair loved for its carnival rides, magic acts, demolition derby, gator show, food trucks and 4-H competition.
• Middleburg Summer Sidewalk Sale – August. A weekend of bargain shopping as Middleburg’s boutiques set out items for sale on the town’s sidewalks.
• TASTE Leesburg – August. Day-long culinary fest where scores of local restaurants, food trucks, breweries, wineries and farm markets offer “tastes” of their best fare.
• Bluemont Fair – September. Fun family-friendly festival from the 1970s featuring live music, arts, crafts, pony rides, a petting zoo and a beer and wine garden.
• Lovettsville Oktoberfest – September. Three-day celebration of beer, music, lederhosen and sizzling bratwurst channeling the German roots of the town. 
• Leesburg Air Show – September. Spectacular aviation festival featuring acrobatic feats, skydivers, vintage aircraft and more at Leesburg Executive Airport.
• Waterford Fair – October. Extraordinary three-day festival featuring traditional arts, craft, reenactments, magic acts, music and intimate tours of historic homes.
• Fall Farm Tour – October. A chance to visit and purchase produce and products from some 40 Loudoun family farms.
• Loudoun Wine Awards – October. Glittering grand tasting reception and gala dinner honoring the year’s best wines, winemakers and wine growers.
• Middleburg Film Festival – October. Start-studded horse country film festival that has become a major stop on the Academy Awards trail.
• Christmas in Middleburg Parade – December. Century-old tradition of tree lighting, carol singing, twinkling lights and horse and hound-filled street parades.