The 3 Best Annual Festivals Around Winchester

Winchester’s calendar wouldn’t be complete without its signature annual gatherings, drawing residents and visitors for music, rides and twinkling lights. Together, these festivals—from spring blossoms to glowing winter pathways—pump millions into the local economy while fostering community pride. Here are this year’s Star Awards finalists in the Annual Festival category.

Shenandoah Apple Blossom Festival

Celebrating its 101st year in spring 2025, the Shenandoah Apple Blossom Festival stretches across ten days and more than 50 events—parades, concerts, breakfasts and a midway carnival. It routinely attracts over 250,000 attendees, making it one of Virginia’s largest civic celebrations. Behind the scenes, a network of 2,000 volunteers and local sponsors fuels everything from the Coronation of Queen Shenandoah to the beloved Firefighters’ Parade. The festival’s economic impact tops $10 million annually, benefiting schools, nonprofits and small businesses across the region.

Clarke County Fair

Held each August at the Clarke County Fairgrounds, this fair blends classic midway rides and agricultural showcases with live music and food vendors. Exhibitors compete in livestock judging, bake-offs and craft displays, reflecting the county’s rural heritage. Special attractions include demolition derbies; tractor pulls and nightly concerts featuring regional acts. With daily admission under $10 and family passes available, the fair remains affordable fun, supporting FFA and 4‑H youth programs through entry fees and sponsorships.

Walking in a Winter Wonderland at Clearbrook Park

From late November through New Year’s Day, Clearbrook Park transforms into a half‑mile illuminated trail. Visitors stroll amid synchronized light displays set to festive music, with timed entry blocks ensuring a smooth experience. Admission runs $8 for ages 3 and up (free for toddlers), rising to $15 at the gate. Special themed nights—Fur‑Legged Day for dogs and Photo Booth Wednesdays—add variety, while hot cocoa and trolley rides offer cozy upgrades. Proceeds benefit local recreation programs and park maintenance.

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