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One of my favorite things to do when I visit a new area is to discover its breweries, cideries, and wineries. You get to meet many locals and find out the scoop on the best places that are off the beaten path. There are so many options for breweries in Winchester, VA!

If you’d also like to explore the drinking from the source (I’m calling these drinkeries) scene in Winchester, VA, check out the breweries, cidery, and wineries you can visit during your trip to this fabulous city in the Shenandoah Valley. Winchester VA craft beverage trail is worth exploring and it’s even easier with the included map.

Breweries in Winchester, VA

Winchester VA Craft Beverage Trail (map included!) | The Common Traveler | image: flight of beers at Broken Window

Broken Window Brewing Company

One of the smaller breweries in town, Broken Window, still manages to offer a large variety of favorites with clever names (“So It’s Come to This” and “Mischief Managed,” for example. Located just off the Old Town Winchester Mall, Broken Window reminded me of a pub with a dark and cozy atmosphere. 

Address: 14 W. Boscawen Street
Telephone: (540) 660-9577

Winchester VA Craft Beverage Trail (map included!) | The Common Traveler | image: beer and steak caesar pizza

Alesatian Brewing Company

Located above the Roma Old Town Wood Fired Pizzeria is the small tap room of Alesatian Brewing. This award-winning brewery offers many types of beer, including some of my favorites, like juicy and NE IPAs. The brewery pays homage to the Alsace-Lorraine region of France, the ancestral home of the owners. 

Visitors can sit at the bar or one of the large communal tables. Due to its relationship with the restaurant, this brewery is a fabulous destination if you want some pizza with your cold brew. Considering the many options, from traditional to unique pizzas like the Steak Caesar, you will surely find something to satisfy your craving.

Address: 23 N. Loudoun Street
Telephone: (540) 667-2743

Winchester VA Craft Beverage Trail (map included!) | The Common Traveler | image: beer flight at Dividing Creek

Dividing Creek Beer Company

Located right on the Old Town Winchester Walking Mall, Dividing Creek is not only easy to find but easy to find a parking space nearby. The large indoor area is complemented with a few outdoor tables for those wishing to enjoy the weather.

If you can’t decide which of their eight beers (plus the occasional hard seltzer) to try, order a flight of four (or two to try them all!). The brewer prides himself on making traditional brews – where an IPA tastes like an IPA, and porters have subtle coffee and chocolate flavors. 

Address: 160 N. Loudoun Street
Telephone: (540) 546-2558

Winchester VA Craft Beverage Trail (map included!) | The Common Traveler | image: flight at Winchester Brew Works

Winchester Brew Works

Visitors will find Winchester Brew Works a few blocks from Old Town Winchester Walking Mall. The brewery is home to a gorgeous mural, making it a perfect stopping spot for those following the Winchester Mural Trail

With plenty of seating indoors and picnic tables outdoors, you’ll surely find a spot at the brewery. The family-friendly brewery has snacks available. The brewery releases new beers weekly and makes hard seltzers and shandy for those wanting options. 

Address: 320 W. Cameron Street
Telephone: (540) 692-9242

Winchester VA Craft Beverage Trail (map included!) | The Common Traveler | image: crispy wontons at Vibrissa Beer

Vibrissa Beer

Located one street away from the Old Town Winchester Walking Mall is Vibrissa Beer & Kitchen. The brewery is large and welcoming inside, with tons of tables and places to sit. The largeness of the indoor space is reflected in the ample outdoor area – with fire pits and different table arrangements beckoning guests to enjoy the weather.

Vibrissa serves wine and beer, which is a good compromise if you’ve got friends who do not enjoy beer. As the name implies, this is an ideal spot to grab a bite to eat while exploring the breweries in Winchester. Choose from an artisan pizza, hamburger, sandwiches, or one of their quick bites – the Teriyaki Wontons were terrific!

PRO TIP: Pick your seat and order through their app (there’s a QR code at every table and chair). You’ll get fast service!

Address: 10 N. Kent Street
Telephone: (540) 313-4551

Winchester VA Craft Beverage Trail (map included!) | The Common Traveler | image: flight at Escutcheon Brewing

Escutcheon Brewing Company

Perhaps the biggest, physical space-wise, of the breweries in Winchester, but it’s also the one furthest away from the downtown action (that’s always the tradeoff, right?). Their true-to-style craft beers are made and packaged right here in Winchester.

In addition to their beers, Escutcheon offers a large selection of hard seltzers for guests who prefer a gluten-free option. Fans of Hefeweizens will appreciate their Spica Hefeweizen Ale’s subtle banana and clove balance.

Address: 142 W. Commerce Street
Telephone: (540) 773-3042

Wineries in Winchester, VA

The Shenandoah Valley is home to some of the best vineyards in Virginia. And the two wineries in Winchester are no exception. What’s the difference between a vineyard and a winery? A vineyard is where the grapes are grown, while a winery is where those grapes are turned into wine. Check out the two offerings in Winchester.

Winchester VA Craft Beverage Trail (map included!) | The Common Traveler | image: rose glass at James Charles Winery & Vineyard

James Charles Winery & Vineyard

If you’re looking for a vineyard with a relaxing atmosphere, take yourself over to the James Charles Winery & Vineyard. Offering lots of seating outside and inside, you’ll surely enjoy both wines and company. Opt for a tasting for $15 or delight in your favorite wine. For the ultimate experience, book the Vintner’s Table Experience. Groups of 6 to 8 enjoy a guided experience by the sommelier carefully paired with a charcuterie board. 

Visitors can order basic charcuterie offerings to accompany their glass even if they do not participate in the Table Experience. Guests who wish to bring their own food can enjoy it and a glass of wine in the outdoor spaces.

PRO TIP: Visit on a cool evening and cozy up to a fire pit with a glass of your favorite vintage. 

Address: 4063 Middle Road
Telephone: (540) 931-4386

Briede Family Vineyards

This family-owned and run vineyard grows a variety of grapes. This vineyard was one of the first in the world to produce Arandell Grapes wines, a hybrid grape. Make sure you try their award-winning Arandell wine for a unique flavor. 

In addition to their estate wines, Briede’s tap room serves French Champagne and sparkling wines. Briede prides itself on making new wines with grapes not traditionally grown in Virginia. This is a laid-back place to try some new experimental and futuristic wine.

Address: 450 Green Spring Road
Telephone: (540) 664-2048

Winchester VA Craft Beverage Trail (map included!) | The Common Traveler | image: apple orchard

Meadery and Cideries in Winchester

Considering that Winchester, VA, is known as the “Apple Capital,” it isn’t surprising that it is home to two cideries and a meadery.

Misty Mountain Meadworks

Considering the beautiful countryside surrounding Winchester and the Shenandoah Valley, it’s unsurprising that local bees produce amazing honey, which means fantastic meads. As the oldest operating meadery in Virginia, Misty Mountain has quality meads with various flavors. What is mead? It’s fermented honey – basically a honey wine.

Their flagship “Wildflower Mead” is a sweet mead that wows first-time tasters. A nod to the local apples can be found in the Tart Apple N Honey mead. There’s even a seasonal mead offered at different times of the year – the Jack O’Hive Pumpkin Pie Spiced Mead is the perfect fall flavor!

Visit the tasting room from Friday to Sunday (check the website for current times).

Address: 661 Warm Springs Road
Telephone: (540) 336-2273

Winchester Ciderworks

Winchester Ciderworks bases its seven signature flavors using a mixture of five different types of apples. Their flavors are off-dry and not overly sweet, making them refreshing.

One of the unique offerings by Winchester Ciderworks is their barrel-aged ciders. The cidery aged their Wicked Wiles (a two-apple variety) in different barrels for nine months: bourbon, rye, brandy, and rum. They also make specialty ciders, including a collaboration with Misty Mountain Meadery. 

Winchester Ciderworks is a great place to try various ciders showcasing the best of Winchester’s apples.

Address: 2504 N. Frederick Pike
Telephone: (540) 686-7632

Old Town Cidery

While Old Town Cidery tore down its tasting room in January 2023. But you can find Old Town Cidery ciders at various local restaurants and shops in Winchester. Check out their Facebook page for pop-ups during the weekend.

Old Town offers two hard ciders, two light ciders, a raspberry rose, and a pearsecco. In other words, visitors will find great basics and fun new twists. 

Address: 326 N. Cameron Street (location temporarily closed)
Telephone: (540) 662-6251

Winchester VA Craft Beverage Trail (map included!) | The Common Traveler | image: apples

Winchester VA Craft Beverage Tour (Maps Included!)

Want to do your own beer crawl? I suggest staying in downtown Winchester at the George Washington – A Wyndham Hotel, so you’re within easy walking distance of most breweries and attractions. While there are organized pub crawls (like the Boos and Brews Brewery Crawl and the Winchester Santa Bar Crawl), you can explore the Winchester VA craft beverage trail on your own any time you like with this suggested itinerary and map!

Start at your farthest point: Escutcheon Brewing. I would take an Uber or Lyft here. From Escutcheon, walk about 16 minutes to Winchester Brew Works. From there, walk about 7 minutes to Vibrissa Beer. This is an excellent opportunity to order something to eat, too. 

From Vibrissa Beer, it’s a straight 5-minute walk over to Broken Window Brewing Company. Next, walk around the corner along Old Town Winchester’s pedestrian mall to Alesatian Brewing Company (about 2 minutes). If you haven’t eaten before, this is another good spot for food (their pizzas are delicious!). From Alesatian, walk about two more minutes along Old Town Winchester pedestrian mall to Dividing Creek Beer Company. That’s it! If you’re staying at the George Washington Hotel, you are only a few minutes walk to your comfy bed!

If you’d like to add spots outside of the downtown area, again, start at the farthest point north. Start at Briede Family Vineyards, followed by Misty Mountain Meadworks. If you’re staying out of downtown, move south to Winchester Ciderworks, followed by James Charles Winery, which is south of town.

One suggestion would be to visit the wineries outside of downtown one day (with a designated driver) and visit the downtown areas on a different day. By dividing the Winchester VA Craft Beverage Trail into two days, you can explore all of the options!

Final Thoughts on Winchester VA Drinkeries

Winchester, VA, is a fun town that knows how to enjoy and celebrate its drinkeries. With a designated driver, a great plan (using one of the maps above), and an open mind to different flavors. Winchester, VA, visitors can enjoy their brewery crawl during a fun weekend getaway.

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I want to thank Visit Winchester VA for hosting my visit. As always, my posts accurately reflect my experiences and opinions.

Happy travels,
Annick, The Common Traveler

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Winchester VA Craft Beverage Trail (map included!) | The Common Traveler shares a map and plan for visiting Winchester's breweries on your own plus adding vineyards, ciders, and meadowy too!

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