07/06/2026
☀️ Summer is officially here, and the Wi******er area is buzzing with incredible things to do! 🍦✨ From historic Old Town to the rolling hills of Middletown, our local community has an amazing lineup of traditions, music, and festivals coming up this season.
Whether you’re planning out your summer calendar or looking to fall in love with the Shenandoah Valley lifestyle, here are 4 can’t-miss annual events to add to your list:
🎨 Old Town First Fridays
Stroll the historic Loudoun Street pedestrian mall on the first Friday of the month (like tomorrow, July 3rd!). Enjoy live music, local artisan pop-ups, and extended shopping hours. (Free family fun!)
Old Town Wi******er, VA
https://www.winchesterva.gov/News-Happenings/Events
🎭 Shenandoah Summer Music Theatre
No need to drive to the city for Broadway-caliber magic. Head to Shenandoah University this summer to catch incredible live productions, including "She Loves Me" and "Beautiful: The Carole King Musical". Shenandoah Summer Music Theatre
https://www.ssmtva.org/
🎡 The Frederick County Fair (July 27 - August 1)
A true cornerstone of local summer heritage! Bring the family out for classic carnival rides, demolition derbies, live music, and local 4-H agricultural exhibits. Frederick County Fair, Virginia
https://www.frederickcountyfair.com/
🍷 Shenandoah Sips @ Belle Grove (Saturday, August 29th)
Unwind at the end of the summer with panoramic Blue Ridge Mountain views in Middletown. Sample exceptional Virginia wines, crisp hard ciders, and craft spirits from local distilleries on the historic plantation grounds. Belle Grove Plantation
https://bellegrove.org/calendar/shenandoahsips
🏡 Thinking about making a move to the area this summer? We know these neighborhoods inside and out—from the best local festival spots to the latest market trends. Reach out today, and let's find a home that fits your lifestyle perfectly!