Winchester-Frederick County Convention & Visitors Bureau

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8 Great Cups of Coffee in Winchester

I must admit, when my wife and I first scouted out the Winchester area to relocate to in late 2015, we immediately went online to see if there were any good local coffee shops. They’re just one of those underlying indicators of a community’s style.  Just about any town can have a Starbucks or Dunkin (and yes, the Winchester area has several of each), but not all of them have enough ‘flavor’ for a successful purveyor of a great local cup of joe.   I’ve been to, and enjoyed, just about all of the area’s coffee shops, and below is my humble impression of those I’ve visited* (in absolutely no particular order).  I sincerely hope you have a chance to check out at least one or two of these the next time you’re in the Winchester area. ~Justin



Hopscotch Coffee


- These guys know their coffee; in fact that’s what dominates their menu.  They really are artisan coffee makers, with a few small pastry offerings.  They also are the only coffee shop in town that roasts on-site (independently branded as “Lone Oak Coffee”).  Situated in what feels like an old garage, they’ve got a unique 2-story set up where you enter upstairs, then below is the seating, roasting and live music area.  And get this – they even have a record shop attached.  Seriously cool. 250 Millwood Ave, Winchester, VA 226015 stars, 15 reviews on Yelp.    


Steamy’s Café

Steamy's 0821.jpgImage by Flickr user Ray Clark

- Want some fresh homemade bagels?  Yes, Steamy’s makes their own unique craft bagels in-house in very small batches.  Their coffee is also expertly crafted, and they have an intimate, eclectic space that is exactly what you envision a college town coffee shop to look like.  This is a great place to warm up (or cool down, depending on the weather) and watch the city go by – located just steps from the Old Town Winchester pedestrian mall, this is a must for visiting on a chilly or drizzly day. 38 E Piccadilly St, Winchester, VA 226015 stars, 59 reviews on Yelp.   


0-60 Energy Café

LampImage embedded from

- One of the more unique settings for a coffee shop; but don’t let the race car enthusiast interior or strip mall location fool you – this is some outstanding, artisanal coffee.  Their specialty is cold drip coffee, but they’ve also got some fresh made breakfast and lunch menu items, with rotating specials. 170-11 Delco Plaza, Winchester, VA 226025 stars, 13 reviews on Yelp.   


Espresso Bar & Café

Bring your friends. I'll bring the coffee. ☕️👍☕️  #workflow #espressobar #coffeeshop #shoplocal #smallbusiness #espresso #exploremore #explorevirginia #downtownwinchester #winchesterva image by Flickr user The Rustic Charmer

– This modern coffee shop, ideally located right on the Old Town Winchester pedestrian mall, is reminiscent of some European coffee shops we’ve seen – clean but cozy, with local artwork adorning the walls.  They’ve got a few breakfast items like a breakfast sandwich and, our favorite, the locally made and incredibly rich little Irish tea breads.  Cuddle up and sneak out back to the secret garden (pictured above) to enjoy your cup of coffee, or sit out front and people watch on the mall. 165 N Loudoun St, Winchester, VA 22601. 4 stars, 51 reviews on Yelp.   


JoGail’s Country Cookin’ Restaurant

Image by Winchester-Frederick County Tourism

– We just had to get this on the list – just about the opposite setting of a college town coffee shop, this local favorite turns out a two kinds of coffee – small and large.  But boy, is this place hopping at 7am on a weekday.  Heavily favored by locals, you’ll feel right at home no matter where you’re visiting from.  The smiles are just as warm as the coffee, and the setting offers a nice view of the mountains and valley.  Located just 20 minutes (but a world away) from downtown Winchester on Rt 50. 5665 Northwestern Pike, Gore, VA 226374 stars, 2 reviews on Yelp.


Firefly Café & Bakery

Image by Yelp user Paul U.

– This made our list as, in addition to a great cup of coffee roasted by Orange County Roasters out of Orange, VA (drip as well as espresso drinks), their food is fresh and fantastic.  Lots of specials, incredible homemade desserts, friendly and happy employees, and a California flair that somehow fits just right in our community.  And for a little dose of philanthropy to sweeten your coffee, they’ve got a long and ingrained history of employing folks with disabilities and other barriers to employment. 3035 Valley Ave. #101, Winchester, VA 226014.5 stars, 18 reviews on Yelp.   


Tropical Island Coffee Café

Image of owner Lloyd by Yelp user Mary M.

– Welcome to our very own Little Jamaica here in Winchester.  Jamaican Blue Mountain coffee (the legit stuff; not the mixed down blends you see so often) is brewed up daily here.  But this is a whole Jamaican cuisine experience – including an incredible jerk chicken, curry goat, beef ox-tails and even a variety of York Castle ice cream flavors.  Just can’t do without your espresso?  They’ve got a full espresso bar menu as well.  Located right around the corner from the Old Town Winchester pedestrian mall, directly across from the beautiful Handley Library. 39 W Piccadilly St, Winchester, VA 226014.5 stars, 81 reviews on Yelp.   


The Hideaway Café

Image from Hideaway Cafe official Facebook page

– Winchester's newest coffee shop has really earned it's name.  Why?  Well, they're in the basement of the old post office building in Old Town, just across the street from Handley Library.  The three women who partnered together to open this great spot have really transformed the space, and it is much larger than you would expect.  With the soft opening just out of the way when I wrote this in late March and a grand opening coming in early April, they're well on their way to becoming a fixture of local university students and evening shoppers and diners.  They'll be offering sandwiches and other goodies soon, and evening live music Fri-Sat.  200 N Braddock St, Winchester, VA 22601.  No reviews as of yet on Yelp.   


* Disclaimer – no businesses paid us or gave us anything to be on this list – we just love coffee and our local businesses, as we hope you do when you visit!

Coming soon – we let our intern loose on the local boutique shopping scene and she’s writing down some insider shopping tips for your next visit!


Location (Map)

Winchester, VA, USA
7 Unique Boutiques in Winchester