Go Outside and Play Guide: Winchester, Virginia

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The perfect base camp awaits for your next Shenandoah Valley adventure. Winchester has a thriving Old Town walking mall with 20+ local restaurants, 4 walkable craft breweries, and an up and coming art scene, not to mention a great outdoor outfitter, surrounded by 275 years of history. All of this within easy reach of hiking, biking, and kayaking for every skill level.

DAY ONE

MORNING

Morning in Old Town warrants a walk to breakfast at the quirky but tasty Steamy’s Café or laid-back Hideaway Café. A short drive gets you to the local favorite Bonnie Blue Southern Market & Bakery. Stop by Mountain Trails Outfitters on the Old Town Walking Mall for any last-minute equipment or supplies, then head west to the Eagle Rock Trailhead on the Tuscarora Trail. You can take a short 15-minute hike to the namesake overlook, or continue on for more beautiful views. This is a 252-mile bypass route of the AT, so you can hike as far or as short as you’d like. You can grab a great to-go lunch from Shaffer’s BBQ and Market or West Oaks Farm Market, both on the way.

AFTERNOON

Afternoon brings you back down the mountain. As you descend, drop by Richard’s Fruit Market for a refreshing homemade peach milkshake or Marker-Miller Orchards for some famous apple cider donuts, baked on-site daily. Then detour to Winchester Ciderworks for fresh UK-style hard cider fashioned in a century-old barn out of apples grown on site. Head back into town to check into the George Washington, A Wyndham Grand Hotel, in the heart of Old Town Winchester, which puts you just feet from a variety of local restaurant options. Or, if you’d like to truly get away, stay at the luxury Inn at Vaucluse Spring or Japanese-themed Pembroke Springs Retreat, both outside of town. 

EVENING

Make sure to check out the showtimes at the popular Family Drive-In Theatre in nearby Stephens City and catch a flick under the stars. Get there a little early on Saturdays as the cars line up!

LOCAL TIP: Outstanding mineral water abounds in our mountains – free always-running spouts can be found off Rt 55 near Eagle Rock or off Wardensville Grade near Pembroke Springs.

DAY TWO

MORNING

Sleep in on your second morning and have brunch at Region’s 117, Oak Stone Pizza, or the Village Square Restaurant in Old Town.

AFTERNOON

Head out to kayak on the nearby Shenandoah River or Potomac River in Harper’s Ferry, stay local and hike the Third Battle of Winchester trails, or go on a guided biking adventure arranged by Element Sports.

EVENING

If you didn’t spend the previous evening exploring in Old Town, this is a must-do today. Stop by Winchester Brew Works for one of their hiking-themed beers and check the showtimes at the Bright Box Theatre for live music, comedy, and more. Or for a paranormal experience, book an Apparition Trail ghost tour, available nightly in Old Town. Save time for a nightcap and live jazz at the Half Note Bar in the George Washington Hotel.

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