5 things to do in Winchester, VA — Thursday, August 27, 2026

Picked each day from verified Winchester-area event calendars. Every listing links back to the organizer.

This story was assembled using AI and public data sources.

1. Thursday On The Farm

   Community at The Homestead Farm at Fruit Hill Orchard, starting 6 p.m.

   Join us for an evening of Bluegrass on the Farm. Dinner is served from 6-7pm, followed by live music from 7-9pm. Bring a lawn chair and enjoy a relaxing night on the farm with family and friends. Dinner menu is posted m…

   Details from the organizer