When the leaves turn gold and the air grows crisp, Winchester, Virginia, transforms into a hub of harvest celebrations, cultural events, and community gatherings. From apple-picking to art walks, there’s something for everyone this fall. Here’s your guide to the best autumn festivals in and around Winchester for 2025—complete with dates, highlights, and links for planning your perfect day out.
ShenArtsFest
Date: September 6, 2025
Art takes center stage during ShenArtsFest, where Old Town Winchester becomes an open-air gallery. Visitors can browse the works of painters, sculptors, and mixed-media artists from across the Shenandoah Valley and beyond. In addition to visual arts, the festival often includes live music performances, art demonstrations, and hands-on activities for kids. It’s a relaxed yet vibrant weekend perfect for pairing with a stroll through the pedestrian mall and stops at Winchester’s charming cafés and shops.
Blessing of the Harvest
Date: September 13, 2025
A heartfelt tradition, the Blessing of the Harvest is a celebration of community and gratitude for the season’s bounty at James Charles Winery. Guests can expect a mix of local music performances, artisan booths, and food vendors serving farm-fresh dishes. Families often attend together, making it a perfect way to introduce children to the region’s agricultural roots. The event typically features a ceremonial blessing, honoring local farmers and producers who keep Winchester’s food traditions alive.
Harvest Hoedown
Date: September 27, 2025
The Harvest Hoedown is a Shenandoah Apple Blossom Festival fall tradition that offers an evening of high-energy fun, complete with live country and bluegrass music, line dancing, and hearty seasonal fare. Picture hay bales for seating, string lights illuminating the dance floor, and neighbors gathering over plates of barbecue and fresh apple cider. It’s a quintessential small-town celebration that welcomes newcomers and regulars alike.
Apple Harvest Festival – Graves Mountain Farm
Date: October 4–5, 11–12, and 18–19, 2025
Held over three consecutive weekends, the Apple Harvest Festival at Graves Mountain Farm is a time-honored Virginia tradition. Guests can pick apples straight from the orchard, take scenic hayrides, and enjoy toe-tapping bluegrass music. More than 70 craft and food vendors line the grounds, offering everything from homemade pies to handwoven baskets. For families, the petting zoo and hay maze are perennial favorites, and the surrounding Blue Ridge scenery makes this festival as beautiful as it is fun.
West Oaks Apple Harvest Festival
Date: October 5, 2025, 11 AM–5 PM
Known for its picture-perfect farm setting, the West Oaks Apple Harvest Festival offers a full day of autumn delights. Guests can wander the pumpkin patch, explore the corn maze, and sample seasonal treats like hot apple cider and fresh donuts. Live music sets the soundtrack for the day, while kids enjoy hayrides, games, and hands-on farm experiences. Local artisans and food vendors round out the experience, making it a one-stop celebration of all things fall.
Festival of Leaves – Front Royal
Date: October 11–12, 2025
Just a short drive from Winchester, the Festival of Leaves transforms downtown Front Royal into a bustling autumn marketplace. This two-day event features dozens of craft booths, regional food vendors, and live entertainment. Visitors can enjoy an Oktoberfest beer garden, a car and bike show, and historic walking tours that highlight the town’s rich past. The combination of small-town charm, fall foliage, and lively street activity makes this festival a must-visit.
West Oaks Fall Harvest Festival
Date: October 19, 2025, 11 AM–5 PM
Rounding out the season, the West Oaks Fall Harvest Festival offers many of the same beloved activities as its apple-themed counterpart, with a stronger focus on pumpkins, gourds, and late-season produce. Expect hayrides, live music, food trucks, and a bustling farm market. Families often use this event to pick out the perfect carving pumpkin or stock up on fall décor before Halloween.
Plan Your Autumn Adventure in Winchester
Whether you’re savoring a caramel apple at West Oaks, exploring fine art in Old Town, or dancing at the Harvest Hoedown, Winchester’s fall festivals offer unforgettable experiences for every age and interest.
About Shenandoah Valley Westminster-Canterbury (SVWC)
Located in Winchester, Virginia, Shenandoah Valley Westminster-Canterbury is a not-for-profit Life Plan community offering independent living, assisted living, skilled nursing, and specialized memory care. Known for exceptional service, compassionate staff, and a vibrant lifestyle, SVWC supports residents in living fully at every stage of life. This fall, discover not just the festivals of Winchester, but the welcoming community at SVWC. Contact us today to learn more.
