Winchester gets a lot of honors.
It’s already been named, by various authorities, “the Best place to Retire in Virginia;” one of the country’s “Best Small Places for Business and Career;” and one of the “25 Best Places to Visit in Virginia.” Last month, it was nominated as a “top adventure town” by Blue Ridge Outdoors.
What keeps Winchester on virtually everybody’s list of “Best Something” is perhaps the variety of experience it offers. History, museums, shopping and dining, performance art and diverse outdoor recreation are all easily accessible here.
Renee Bayliss of the Winchester-Frederick County Convention & Visitors Bureau, told us, “Our history stretches back over 275 years, and it has been preserved in our museums and historic district. We have museums for children and families, history buffs, and art lovers. Outdoor recreation opportunities include horseback riding and kayaking, hiking to scenic vistas, off-road ATV tours, or birdwatching at our wetlands preserve. Old Town is buzzing with activity, but in just a few minutes you can be enjoying a scenic drive and visiting our locally owned farms.”
Bayliss added, “I would say that September is a great time to visit because the apples are ripe for picking at the farm markets. The ones that offer “pick your own” are Rinker’s and Marker-Miller.
“We also have the outdoor exhibit, “Big Bugs,” at the Museum of the Shenandoah Valley,” Bayliss added. (Another exhibit at the MSV that just opened late in 
Augusts is “An Adventure in the Arts”–paintings, sculptures, drawings, prints, photographs, and mixed-media works by some of America’s most celebrated artists, including Thomas Moran, Childe Hassam, Jackson Pollock, Andy Warhol, Elaine de Kooning, and others.)
Bayliss continued, “Of course the weather cools down a bit in September so it is a more comfortable time to enjoy that. Also, it’s a good time to enjoy fall treats like apple cider donuts and Rinker’s apple cider.”
Visiting with the kids in tow? Make sure to stop by the Shenandoah Valley Discovery Museum. While they are operating at a reduced capacity, they are open. Make reservations online and treat your kids to a variety of educational fun and games.
Like many towns in the Shenandoah Valley, Winchester has had to cancel or postpone some events and festivals due to COVID-19 concerns. But one in Winchester that is still scheduled to be held is the Shenandoah Valley Apple Harvest Festival, September 19 – 20 at the Frederick County Fairgrounds in Clear Brook. The long list of activities includes: craftsmen and artisans, a classic car and hot rod show, local craft beers and ciders, live music, food concessions with everything from apple pie to BBQ, plus plenty of kids’ games and pony rides. Presented by the Rotary Club of Winchester, with proceeds going to local nonprofits.
Besides all that you can see in Winchester, how you see it can be rewarding, too. In September, it is gratifying to simply tour the area by car. With orchards, mountain views, pastoral farmland and quiet back roads all beckoning travelers, car trips are a can’t-miss option. And Winchester has a number of planned itineraries for you. Drive the “Shenandoah Valley Hop,” for instance, a three-day jaunt starting in Winchester, then to Harpers Ferry, then to Shenandoah National Park and finally to Luray. Suggested routes and stopping points guarantee you’ll see some of the most memorable sights the Valley offers. Other trip ideas such as the Retro Road Trip and the Girlfriend Getaway may be found here. https://visitwinchesterva.com/trip-ideas/
Make your first stop the Winchester-Frederick County Visitors Center and Civil War Orientation Center located at 1400 S. Pleasant Valley Road, Winchester.
Banner photo courtesy Robert Harris/Virginia Tourism Corporation