All Day

National Finals – Sheepdog Trials

Belle Grove Plantation 336 Belle Grove Rd., Middletown

The National Sheepdog Finals are the North American championship of working dogs and their handlers from across the United States. One hundred and fifty competitors have earned the right to compete in Finals through their success at local sheepdog trials throughout the year. The event will be on the large front field at Belle Grove ... Read more

Haunted Nightmares

Hill High Farm 933 Barley Lane, Winchester

Haunted Nightmares Haunted House Step inside and experience horror like never before! Haunted Nightmares is an intense attraction that features professional sets with theatrical lighting and special effects. (Our attraction is open during daylight hours on Saturdays and Sundays with a less aggressive show for a younger audience.) Escape Rooms Come Try Our New Escape ... Read more

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Apple Harvest Festival

Marker-Miller Orchards 3035 Cedar Creek Grade, Winchester

Saturday, Oct. 9 (9am-5pm) & Sunday, Oct. 10 (10am-5pm) Everything apples! Multiple varieties of apples to choose from, with pick your own available. Apple cobbler and apple cider slushees can be enjoyed while sitting on the front porch or listening to the music each day from 1-3 P.M. For the kids we have a playground ... Read more

Master Gardener’s FallFest

Richard’s Fruit Market 6410 Middle Road, Middletown

When the garden slows down in the fall, get a head start on next year with VCE Master Gardeners at the FREE FallFest. Sponsored by the Northern Shenandoah Valley Master Gardener Association, this event includes talks from Master Gardeners, as well as demos, crafts, and giveaways. All talks, demos, and crafts are free to the ... Read more

West Oaks Fall Festival

Come on out to West Oaks Farm Market's 4th Annual Fall Harvest Festival for a full day of Fall fun on the farm! Corn Mazes, Pumpkin Picking, Hayrides, Apple Picking, Live Music, Kids Activities, BBQ Chicken Dinners, tons of Fall Craft Beers, and so much more!


Broken Window Brewing Co. 14 W. Boscawen Street, Winchester

Please join us for our second annual Dogtoberfest! Boscawen street will be closed down and lined with tents for you to meet adoptable dogs and enjoy wine, craft beer, live music, local food trucks, vendors, and MORE in this block party-style event! FREE ADMISSION $6 DRINK TICKETS (beer, wine, mimosas) Live Music: 90 Proof Band ... Read more

Apples and Hard Cider: A History

Winchester Ciderworks 2502 North Frederick Pike, Winchester

This history program will provide a general background on apple cultivation and cider production worldwide, in particular, Frederick County. Join us at Winchester Ciderworks, for this special event, in collaboration with the Winchester-Frederick County Historical Society. Founded in 2012, Winchester Ciderworks makes handcrafted Virginia hard cider with apples from their own orchard. Come visit their ... Read more

Free Fireworks Spectacular

Middletown Community Park Senseney Avenue and Second Street, Middletown

Please join us on October 9th as we celebrate the 225th anniversary of our beloved town, Middletown, AND the 40th anniversary of our friends at the nonprofit Blue Ridge Hospice. We are holding a free fireworks show for the public that will be displayed to music. You don't want to miss this!

Click here to view more upcoming events on our Winchester VA Events Calendar.