by Sigourney Pierson | Oct 1, 2026 | Annual Events, Upcoming Events
Each year, at the end of October, Old Town Winchester transforms into a haunted destination, offering guided ghost tours that blend history and legend. Guests walk through historic streets and alleys, hearing chilling tales of colonial spirits, Civil War soldiers, and...
by Meghan Nicholson | Aug 17, 2026 | Annual Events, Upcoming Events
Experience the Fall Pumpkin Harvest Festival at Great Country Farms in Northern Virginia! Pick your perfect pumpkin directly from the patch, get lost in a corn maze, and enjoy freshly made cider donuts. Weekends feature pig races, live music, and P-Rex the...
by Meghan Nicholson | Aug 17, 2026 | Annual Events, Upcoming Events
Head to West Oaks Farm Market in Winchester, VA, for hayrides, a corn maze, and a pumpkin patch. Enjoy apple picking, live music, delicious food vendors, and attractions for children in a lively and enjoyable farm atmosphere.
by Meghan Nicholson | Aug 17, 2026 | Annual Events
Get ready for aviation and automotive fun at Wings & Wheels at Winchester Regional Airport! This family-friendly event features stunning aircraft displays, classic car show, local vendors and businesses, delicious food trucks, and activities for all ages.
by Sigourney Pierson | Mar 1, 2026 | Annual Events
On the First Friday of every month, Old Town Winchester Celebrates the Arts! Downtown Winchester plays host to artists with special gallery events, musicians playing in restaurants and cafes, and many shops stay open late. Every month is something a little...
