9 Ways to Pass a Rainy Day in Winchester

Rainy Day in Winchester by Aaron Riddle
Image courtesy Aaron Riddle Photography

We don’t get all of these beautiful natural surroundings for free here in the northern Shenandoah Valley – we must pay for them with the occasional rainy day. But don’t let that dampen your adventurous spirit or dash your hopes for a fulfilling visit. Here’s an inclement weather guide to help out the next time you’re in the Winchester area and the sun takes a day off…


1) Warm Up With a Cup of Coffee

Photo of Espresso Bar and Cafe by Winchester-Frederick Tourism

This can mark the beginning, middle or end of any day here in the area. Fortunately, we’ve got a pretty impressive array of local ‘joe’ hotspots that we’ve already listed out for you in our previous Coffee Hotspots blog. We even marked which ones have free wifi for you…


2) Discover a New Restaurant

Get your indoor al fresco dining fix at Umberto’s

We’ve got over 200 restaurants here in the Winchester & Frederick County area, so no excuses. Treat yourself to a fine dining experience somewhere like Joe’s SteakhouseGeorge’s Food & Spirits, Village Square, Violino Ristorante or Region’s 117 Lakefront Dining. Or maybe try one of our newer restaurants like Oak Stone Craft Pizza, Sclafani’s, Sweet NOLA’s, Paladin Bar & Grill or Smokey T’s Southern Kitchen.


3) Catch a Live Show

Image of the Bright Box from Facebook

Check out the calendars of Blue Fox, Brewbakers, the Bright Box, Stephen’s Jazz Café, SU Conservatory, Sweet NOLA’s, and the Winchester Little Theatre.


4) Catch a Canned Show (aka a Movie)

Image of the Alamo Drafthouse from their website

The Alamo Drafthouse is more than a top-notch, affordable movie theatre – they run a dizzying amount of special screenings, events and special programs. If you’ve got RainX on your windshield, the Family Drive-In is great on a rainy evening as you’ll avoid the crowds. And of course, we’ve got the AMC Theatre at the Apple Blossom Mall if you want to make an afternoon of it and wander around the mall.


5) Go Hiking

Image of small falls near Pinnacle Rock on the Tuscarora Trail by Winchester Tourism

Hiking on a drizzly day can be a transformative experience, as the earth comes alive in the rain and you’ll be at one with your surroundings. A couple of important caveats: a) thunder and lightning are a no-no, b) heavy rain can cause dangerous situations in the mountains, so be cautious and c) make sure you hit Mountain Trails outfitters in Old Town Winchester first to make sure you’ve got the gear, maps and local expertise to maximize your trip.


6) If You’ve Got Kids, Try These

Image of a brook trout at the Shenandoah Valley Discovery Museum by Winchester Tourism

The Alamo Drafthouse, the Shenandoah Valley Discovery Museum, the Apple Blossom Mall (has a kid’s play area), and the Museum of the Shenandoah Valley (check their site for current exhibits).


7) If Not, Have a Drink at One of These…

Image from Alesatian Brewing Co. Facebook page

…and be thankful for the rain as it’s growing more local grapes/hops/apples/grains that are used to make what you’re drinking. These are all on the brand new Shenandoah Spirits Trail, but we’ll break them down for you anyway. Breweries: Alesatian Brewing Co, Broken Window BrewingEscutcheon Brewing Co., Winchester Brew Works. Wineries: Briede Family Organic VineyardJames Charles Winery, Valerie Hill Winery. Cidery: Winchester Cider Works.


8) Finally Get to That Museum

Image of Abram’s Delight historic house by Winchester Tourism

Been looking for an excuse to get out to one of our great museums?  Now’s a perfect time.  Open year-round:  Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum, Old Court House Civil War Museum.  Open seasonally (check site for dates):  Abram’s Delight, Belle Grove Plantation, George Washington’s Office, Newtown History Museum (Stephens City), Patsy Cline House, Stonewall Jackson’s Headquarters Museum.


9) Or, the Default Rainy Day Activity: Go Shopping!

Image of shopping in Old Town Winchester by David Polivka

First, check out our Boutique Shopping Guide we created recently to get you around to all the cool, local boutique shops. But don’t stop there; our main shopping hotspots include:

And yes, if you insist, we even have a Costco 🙂


As always, no business paid to be on this list – we just wanted to help get you out of that nice hotel room and exploring, even if it is a bit rainy!