The 5 Best Community Events/Festivals Around Loudoun

From seasonal celebrations to longstanding traditions, community events and festivals in Loudoun County, VA, offer more than just entertainment—they bring people together. These gatherings support local artisans, showcase regional heritage, and provide family-friendly fun. Whether it’s a weekend full of flowers or a dance-filled evening, there’s something special about events that spark joy and connection. Here are the winners from the 2025 Best of Loudoun contest.

Leesburg Flower And Garden Show

Each spring, the historic streets of downtown Leesburg transform into a botanist’s dream. The Leesburg Flower and Garden Show draws tens of thousands of visitors who stroll among garden displays, shop for plants and décor, and get inspired by horticultural creativity. Hosted by the Town of Leesburg, this two-day festival has been a mainstay for more than 30 years, featuring landscape professionals, educational opportunities, and food vendors. It’s more than a flower show—it’s a celebration of outdoor living, design, and local pride.

Loudoun County Fair

What began in 1936 as a humble agricultural event has blossomed into a weeklong tradition showcasing Loudoun County’s rural roots. The Loudoun County Fair blends classic fair fun with 4-H exhibits, live music, rodeos, and homegrown competitions. The fair is organized by a volunteer board and deeply tied to the region’s farming culture, emphasizing education, livestock, and community connection. It’s the kind of event where blue ribbons matter, pie-eating contests draw a crowd, and every generation finds something to love.

The Ladies Board Annual Rummage Sale

For more than 80 years, The Ladies Board Annual Rummage Sale has brought bargain hunters, collectors, and treasure seekers together for a two-day shopping experience like no other. With proceeds supporting scholarships and patient care at Inova Loudoun Hospital, this massive community sale combines feel-good giving with unbeatable deals. Volunteers work year-round to prepare for the sale, which features thousands of donated items from furniture and clothing to electronics and antiques. It’s part fundraiser, part tradition, and 100% community spirit.

Lovettsville Oktoberfest

Small town, big celebration. That’s the vibe at Lovettsville Oktoberfest, where German heritage takes center stage each September. The weekend-long festival features live music, a traditional beer garden, authentic food, and cultural performances. Hosted by the Town of Lovettsville, the event also includes a Kinderfest for children and a bustling street market filled with crafts and local vendors. It’s a tribute to the town’s German roots, and a reason locals and visitors alike mark their calendars every fall.

Saturday Line Dancing - LineDance4You

There’s a certain kind of magic in synchronized boots and country beats. LineDance4You offers just that with its Saturday Line Dancing events, where people of all levels are welcome to learn, laugh, and let loose. Based in Leesburg, the group’s motto is “Dance first. Think later.” They host regular dance nights with beginner-friendly instruction and a high-energy social atmosphere. It’s a modern twist on community gathering—less potluck, more playlist.

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