6 Totally Unexpected Finds in and around Winchester

There’s a certain advantage to being the new guy in town (in addition to being able to say “oops, sorry, I’m new here” when I mess something up).  I’m on a mission to discover things, and pretty much everything is new and exciting.  My wife and I have definitely stumbled across some pretty cool stuff, and a number of things have been so unexpected I felt compelled to do a whole blog post about them.  I’m still finding new stuff, so this is in no way an exhaustive list, and I’ll be adding to it in the future.  I encourage you to get out there and find something even more unexpected and let us know about it!  Never stop exploring, even especially in your own backyard.

A Virginia Oyster Trail Restaurant  

So we’re a few hours from the Eastern Shore here in Winchester – didn’t stop us from getting the first inland location on the internationally recognized Virginia Oyster Trail. George’s Food and Spirits Restaurant (attached to the beautiful George Washington Hotel in Old Town Winchester) proudly serves Rappahannock oysters, and just recently got the trail designation. See, we just saved you a trip to get some great oysters.  You’re welcome.   103 E. Piccadilly Street, Winchester, VA 22601

A Japanese-Inspired B&B  

Even a lot of the locals I speak to aren’t aware of this gem located out near Star Tannery, a beautiful 25-30 minute drive SW of Winchester.  Pembroke Springs Retreat is idyllically situated in a small valley with gorgeous sweeping views of the Great North Mountain.  Traditional spring-fed baths, outstanding food, surprising hiking trails, and truly unique rooms featuring different levels of Japanese style can be found here.  This is a pretty grown-up destination, though, so you’ve got a good excuse to leave the kids at home with the grandparents when you visit (“Sorry Mom & Dad, they don’t allow kids under 4 – here they are.  See you in a few days!”).  6238 Wardensville Grade, Star Tannery, VA 22654

Hiking, Vistas and a Waterfall  

No, seriously, this is right here in Frederick County.  Haven’t heard of the Tuscarora Trail?  Well, this is the Appalachian Trail’s cooler, tougher brother.  Under constant development by the Potomac Appalachian Trail Club (PATC), this 252-mile bypass route (and official side trail) for the Appalachian Trail goes just west of Winchester.  A lot of this is ridgeline on or near the Virginia/West Virginia border, and a bunch also goes through the George Washington National Forest.  Well marked but way less busy than the AT with arguably much better vistas in this region (and a small waterfall near Pinnacle Ridge), you’ll definitely be able to one-up all your buddies who think they’ve done all of Virginia’s AT.  Check out PATC Map F and L (available locally at Mountain Trails in Old Town) for more detail, including shelters, access points, and POI’s.  We’re also working to get all of these trails on Google Maps (a pretty time consuming project – it’s in the works!).  Access points in the George Washington National Forest here, Shawnee Land here, and Gore here.

A Yoga Healing Trail  

Bust out your crunchy granola and head on over to this free trail, hidden right here in the city.  A surprisingly quiet, relaxing and meandering spur from the city’s Green Circle Trail, this is located just steps from the Visitor Center.  We saw (and heard) a ton of birds in the tall, healthy canopy of mature trees that make for a great sunny-day hike, making this a relaxing and enjoyable jaunt for anyone (even if you don’t do yoga).  And yes, there are even signs saying its okay to go ahead and hug the trees. Parking lot near 1313 Opequon Ave, Winchester VA 22601

Free Mountain Spring Water  

No, please don’t take your prized Corkcicle tumbler that you just picked up at Simply Charming down to Abrams Creek in the city and start sipping.  We’re talking about underground fed, crystal clear, amazing mountain spring water, tapped and running 24 hours a day in at least two locations we’ve found.  Just to be clear, this is ‘drink at your own risk’ water as it’s not regulated by anyone.  Good, now we can tell you where to find it.  One is on Hwy 48/55 (aka Wardensville Pike) right here, and one is at the entrance to Pembroke Springs Retreat on Wardensville Grade, right here.


A Jazz Café 

Another great spot that a lot of locals I speak to don’t know about.  Stephen’s Jazz Café is a really cool spot with great food located in Winchester right next door to John Kirby’s house.  John Kirby, if you didn’t know, was a big band era jazz musician from Winchester.  Stephen’s has regular live performances, many of which tap into the amazingly talented Shenandoah University Conservatory students musicians.  See, we just saved you another trip into Northern Virginia.  You’ve got a great jazz experience right here!  440 N Kent St, Winchester, VA 22601

Side note, I know there’s an incredible and deep history here in the Winchester area (that includes but is so much larger than the Civil War), but that’s such a big and different topic that we’ll do a whole different post along those lines…

*Disclaimer – no businesses paid us or gave us anything to be on this list – we just love making all these discoveries, as we hope you do when you visit!