5 Things to Do In and Around Winchester This Weekend

Here is a quick, scenic guide to the best things to do around the beautiful Shenandoah Valley this weekend:

  • Sip Wine with a View at James Charles Winery: Relax on the expansive outdoor patio with a tasting flight and take in stunning panoramic views of the rolling hills and distant mountain ridges.

  • Relax at the MSV "Gardens at Night" Concert: Bring a lawn chair on Friday night to enjoy live music, food trucks, and a sunset stroll through seven acres of breathtaking, formal gardens.

  • Pick Fresh Treats at Marker-Miller Orchards: Head into the hills of this 325-acre family farm to pick seasonal fruit, take in mountain vistas, and grab a box of their famous apple cider donuts.

  • Stroll and Dine on the Old Town Pedestrian Mall: Walk the charming, tree-lined brick pathways of historic downtown and grab a patio table for outdoor dining framed by beautiful 19th-century architecture.

  • Visit the Cider Room at Mackintosh Fruit Farm: Take a scenic drive to Berryville to enjoy fresh farm-to-table lunch specials and craft hard ciders overlooking peaceful, rustic orchards.