Road Trips, Small Towns

Winchester, Virginia: 7 Reasons You Should Visit

Winchester, Virginia–a quaint little town just south of the West Virginia border–is not a tourist mecca.  But for the life of me, I can’t understand why.  This little town has everything going for it, from fine dining to quaint historic buildings to a super-photogenic downtown pedestrian center, all of it located less than 80 miles outside of the nation’s capitol.  I only spent one night in Winchester, and yet I came up with seven great reasons to visit.  That’s almost one reason per hour, if you only count the hours I was awake.

The Gateway to Shenandoah

I didn’t just throw a dart at a map and decide to visit Winchester, Virginia.  I live in Pennsylvania and, like anyone else living in the Northeast with the same goal–to visit Shenandoah National Park–I passed by on my way to the mountains.  Winchester, Virginia is located less than thirty miles north of the northernmost entrance to Shenandoah; I left Winchester a little before 10 in the morning and was driving through the park gates before 10:30.

A Great Bar Scene

To be fair, I visited on one of the biggest party nights of the year–the night before Thanksgiving.  Seriously–I think it is even bigger than New Year’s Eve.  But still, the bar scene in Winchester was alive and well.  We first checked out Union Jack, where my husband enjoyed far too many pints of cider (which, to his delight, were on tap); Union Jack was warm, inviting, and quite crowded at 5:00 on the Wednesday before Thanksgiving.

Even in the somewhat deserted pedestrian area, the ars filled up with people of all sorts.  Sitting on a stool at Brewbakers, I at once observed an older townie man sitting alone, two college-aged guys with gauges in their ears, a woman wearing an expensive looking, fur-lined pea coat and scarf, and us–two out of town guests observing it all.  And everyone seemed to get along.  Even the bartender–a mid-30’s woman with a cute southern-ish accent and a cheerful disposition–fit the evening.  Because in life as in interior design, if nothing matches, everything matches.

Fine Dining at Violino

I hate to admit it, but I did very little research on Winchester restaurants before arriving.  We were in town on the night before Thanksgiving and I honestly wasn’t planning on having a huge meal.  But you know what they say about the best laid plans…

We chose Violino because it looked cute from the outside, it was on the pedestrian mall where we were bar hopping, and it was open.  A surprising number of restaurants close down the day before Thanksgiving, presumably getting ready for all of the stuffing, baking, and roasting to come.  I have never had such an amazing meal completely by accident.

I made a reservation for 8pm–at 6pm that same night–and as soon as we walked in I could tell we were the last table of the evening; I immediately began to feel badly.  However, the bad feeling was all my own doing.  The wait staff could not have been more kind or attentive, and our meals could not have been more expertly prepared.  Truly, if there was a time for cutting corners, that would have been the time.  Yet our server took his time to explain the menu–and the specials–and the chef clearly put everything he had into our meal.

Because my husband is an unstoppable force of nature when it comes to food–especially after a few pints of cider–he insisted on an appetizer.  I can hardly blame him, as they were offering one of his favorite things in the world–a platter of cured meats.  He enjoyed cured ham, duck, venison, boar, and beef; the ham–prosciutto–was served traditionally with melon and a tad untraditionally with pineapple.  Have you ever had pineapple wrapped in prosciutto?  If not, I truly feel badly for you.  It was a revelation.  Hawaiian pizza has nothing on this much classier combo.

For our entree, we both ordered off the specials list; my husband had the osso bucco and I chose the seafood ‘risotto’.  I put risotto in quotes because the plate that was presented to me was not merely risotto.  It as a seafood feast, piled high with anything that ever swam, crawled, or stuck to the bottom of the ocean floor–with some pretty awesome risotto to boot.  I said it over and over again as I enjoyed my family-sized portion:  this may be the best thing I’ve ever eaten.  And I eat a lot.   I feel like I can’t do this meal justice by simply talking about it, so I’ll include a photo:

Everything was cooked separately–the scallops were seared, the prawns were grilled, and the oysters were Rockafeller-ed (yes, I just made that a verb).  It was a personal seafood buffet all for me–on the night before Thanksgiving.  I took a moment to be extremely thankful for the fact that I had a day of hiking planned between that meal and my four-course turkey dinner the following night (I still maintain that I gained at least five pounds in as many days on this trip.)  To put this meal in perspective, I have been married to my husband for six years.  He asked to taste one of the oysters.  I thought for a long, long time before–extremely reluctantly–I said yes.

And I still regret sharing that oyster.

Classy Lodging

Remember all those pints of cider my husband enjoyed at Union Jack?  They were all responsibly consumed less than a five minute walk from our hotel, The George Washington Hotel Winchester.

It would be unfair of me to say that The George Washington Hotel is the nicest hotel in Winchester, as I’ve only ever stayed at the George Washington; however, I can’t imagine what a better option would look like; the George Washington had it all.  As soon as we entered the lobby, my husband–dressed for travel–looked down at himself and said ‘yeah, I’m not fancy enough to be here’.

The George Washignton lobby features a beautiful bar area (pictured just beyond the focal-color flowers in the photo, left) complete with baby grand piano and full walls of multi-pane windows.   There’s also a pool and jaccuzzi area as well–on the ground floor–decked out with roman columns and absolutely spotless.

Our room was huge, with a full-sized sofa and ample office area; the shower was a giant, marble-and-glass marvel.   Honestly, I’ve not had the pleasure of staying in a nicer hotel.  And all of this mere steps from the historic downtown core and the restaurant-and-shop-lined pedestrian mall.

I was–and still am–truly sad that we were only staying for a night.  I would have loved to enjoy a long weekend at The George Washington, enjoying more of what the hotel–and the town–has to offer.

Main Street Shopping

I actually shopped during my time in Winchester, which is very unlike me.  But I was in need of something specific–namely black leather knee-high boots–and so I stopped in to a shoe shop on the pedestrian mall, lured by the display in the full-size glass storefront.  And that’s the thing about the pedestrian mall area–all of the stores have storefronts, with beautiful displays intended to entice you inside.  And trust me, had more shops been open on that cold, dark, day-before-a-holiday night, I would have done some damage.  As it was, my poor husband was forced to stand around and watch me press my nose against the glass of several shops and listen to me bemoan the fact that we’d be gone by the time they opened in the morning.

Reasonable Prices

Speaking of everything I’ve said above, there’s yet another reason to love Winchester.  After all, lots of places have great food, shopping, and proximity to national parks.  But not many of them are as budget friendly as this charming Virgina town. The valet parking at The George Washington Hotel was five dollars.  That’s US dollars.  Five of them.  Not thirty, not forty.  Five.  While window shopping, I discovered a beautiful hand-thrown piece of pottery in a store window, and peered closer to read the price tag: $45.  Our meal at Violino was less than $100 for two people, including alcoholic beverages–which is impressive given the fact that I was served half of the contents of the Atlantic ocean and possibly a fraction of the Pacific, too.

Charming People

From the woman who checked us into our hotel, to bartenders number one and two to, to the kindly waiter who humored my a-little-drunk-on-wine husband, everyone I encountered in Winchester was warm and welcoming.  And that, more than anything, makes a town worth visiting.

I’d jump at the chance to return to Winchester and spend a bit more time.  I’m sure I could find even more things–and people to love.

Disclosure:  I was hosted by The George Washington Hotel Winchester; however, all opinions are, as always, my own.  Please see my disclosure statement page for more information.

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