Few quests are more satisfying than tracking down the best pizza in Winchester, VA. The hunt isn’t just about chasing that perfect blend of sauce, cheese, and crust—it’s the anticipation each time a box opens, the familiar aroma wafting up to greet you. My first trip to Winchester was a happy accident, led by the promise of a place where wood-fired ovens glow and every corner pizza shop has its own loyal following. With every slice, the city’s pizza scene revealed itself: sometimes bold, sometimes classic, always memorable.
If you’ve ever stood at the fork in the road between New York-style foldable slices and hearty deep-dish, you’ll appreciate Winchester’s diverse offerings. Whether you’re after a delicate thin crust crackle or that iconic cheese pull, you’re in the right place. This guide gathers the local favorites and unsung gems, so each choice is a sure bet. There’s a story behind every pizza joint here—and you might just find your new favorite along the way.
1. Roma Old Town Wood-Fired Pizzeria
Set in the heart of Old Town at 21 N Loudoun St, Roma Old Town Wood-Fired Pizzeria draws people in with its glowing oven and lively buzz. Walking in, you feel like you’ve stumbled on a local secret—staff are friendly, and the aroma of fresh dough fills the air.
What sets Roma apart is the genuine wood-fired crust: crisp outside, pillowy inside, and perfectly charred. It’s the kind of pizza that makes you pause after the first bite. Don’t miss the Margherita, which lets the simple, high-quality ingredients speak for themselves. The Quattro Formaggi is another standout, rich without being overwhelming.
With vegan, vegetarian, and gluten-free options, everyone finds a slice of happiness here.
2. Oak Stone Craft Pizza & Bar
Oak Stone Craft Pizza & Bar, tucked at 1000 Valley Ave, gives off a welcoming vibe that feels just right for a laid-back evening. I’ve found the staff attentive without hovering, and the open kitchen adds a fun, lively feel to your meal.
What makes Oak Stone stand out is its creative approach to pizza. The crust is thin, golden, and acts as a perfect base for bold flavors. Try the Roasted Veggie pizza—the blend of fresh vegetables and just the right touch of cheese lets every ingredient shine. The Truffle Shuffle pizza is another favorite, balancing earthy mushrooms with a whisper of truffle oil.
Vegetarian, vegan, and gluten-free options mean everyone can dig in.
3. Umberto’s Pizza and Pasta
Sitting in Umberto’s Pizza and Pasta at Delco Plaza, you sense a true neighborhood feel. Staff greet regulars by name, and new faces are welcomed with warmth. My last visit ended with friendly chat and a slice that was more than worth the trip.
Umberto’s stands out for classic, no-nonsense pizza that doesn’t lean on flashy trends. The crust is sturdy, the sauce has a touch of sweetness, and you can tell it’s all homemade. Their Veggie Pizza bursts with color and flavor, while the Bianca White Pizza delivers a creamy, garlicky punch—both great choices for any pizza fan.
Portions run generous, perfect for sharing, and the vegetarian and vegan options mean everyone gets a seat at the table here.
4. Pizzoco Pizza Parlor
Pizzoco Pizza Parlor on N Loudoun St never blends into the crowd. It’s all about craft here—dough made from scratch, hand-cut vegetables, and a sauce full of bright California tomatoes. The first time I tried Pizzoco, the crust alone made me stop and rethink what pizza could be.
This spot stands out for taking every ingredient seriously. There’s no trace of shortcuts, only layers of fresh, vibrant flavor. The Garden pizza is a must—a pile of fresh veggies on their signature crust. For a little something extra, try the Classic Cheese. Simplicity here is far from boring.
Even the little details shine, from the digital payments to the cheerful service—all adding up to a slice that’s truly Winchester.
5. Claudio’s Pizzeria
There’s a comforting charm to Claudio’s Pizzeria on Valley Ave. This is the kind of place where the pizza doesn’t try too hard—it just delivers, every single time. On my last visit, I was greeted with genuine smiles and the tempting sight of classic pies ready to go.
Claudio’s keeps things simple, and that’s the magic. Their crust is chewy but never soggy, with a mellow sauce that balances every bite. The Supreme Pizza is a crowd-pleaser, loaded with fresh toppings and perfect for sharing. If you like your pizza classic, Claudio’s plain cheese captures why locals keep coming back.
The casual setting is ideal for both quick takeout and relaxed, no-fuss meals with friends.
6. Alesatian Brewing Company
+1 504-667-2743
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Alesatian Brewing Company sits above Old Town’s hum, just upstairs from Roma, making it a hidden delight for pizza fans. A trip here feels like sneaking up to a friend’s loft after hours—brick walls, a relaxed crowd, and always something fresh out of the oven. My last visit stretched into a leisurely evening, thanks to the easy pace and friendly staff.
Pizza is center stage, and the menu leans on inventive combinations you won’t find everywhere else. The Roasted Veggie pizza lands just right: charred edges, sweet peppers, and a sprinkle of fresh greens. If you want to keep it classic, the Margherita balances tangy tomato with creamy cheese over a crisp crust.
It’s a spot where flavor takes the spotlight, and even vegetarians have plenty to cheer about.
7. 3.14 Pizza
If you ever feel like pizza with a side of math puns, 3.14 Pizza on Berryville Ave doesn’t disappoint. The first time I called in an order, I was tempted by the playful menu. Picking up my box, I knew right away it wasn’t average chain fare, but something crafted with real care.
What separates 3.14 is their balance—cheese doesn’t drown the sauce, and the crust stays light and crisp. The Veggie pizza is a smart pick, layered high yet never greasy. Their Spinach and Feta option also stands out, offering a fresh, slightly tangy twist you don’t see everywhere.
Portions are generous, and the friendly delivery makes this a top choice on nights in.
8. Ledo Pizza
Ledo Pizza at Gateway Drive brings something different to the Winchester pizza scene—namely, their unmistakable square pies. When I first visited, the sight of those crisp-edged slices felt like a fresh twist on the familiar pizza ritual. Friendly staff and a relaxed space made it easy to settle in and enjoy.
What makes Ledo Pizza unique is its slightly sweet, flaky crust paired with generous layers of cheese. The Veggie Pizza is a top pick, piled with plenty of vegetables and perfect for anyone after big flavors without heaviness. The classic cheese square delivers comfort with every bite.
With plenty of options for all tastes and reliable takeout, it’s easy to see why locals return again and again.
9. Benny Meleto’s
Benny Meleto’s on E Boscawen St is famous in Winchester for slices that push the definition of “large.” The moment you walk in, the energy feels young and welcoming. My first time, balancing a single slice on a tray felt like a quirky rite of passage.
What sets Benny’s apart is the value and that perfect balance: thin crust that stays crisp, sauce and cheese that don’t overwhelm, and generous, fresh toppings. The classic cheese slice is a local legend, but the Veggie option never disappoints, piled high and full of flavor.
For an experience that’s a little out of the ordinary, Benny Meleto’s and its giant slices are hard to forget.
10. Cafe Del Sol
Cafe Del Sol on Featherbed Ln brings a modern touch to Winchester’s pizza lineup. My last visit made it clear—this is where Mediterranean charm meets casual comfort. The staff handle every rush with calm efficiency, and you can always count on a clean, sunlit dining room.
The pizza at Cafe Del Sol stands out for its fresh, bright flavors and crisp, thin crust. The Mediterranean pizza is the showstopper, loaded with roasted vegetables and a sprinkle of feta. Their Margherita is another win, showing off simple, quality ingredients in every bite.
Everyone, from vegans to gluten-free diners, finds a thoughtful option here. It’s the perfect spot when you want pizza that feels a little lighter, but just as satisfying.
Frequently Asked Questions
What pizza places in Winchester, VA have vegetarian or vegan options?
Many top spots offer plant-based and vegetarian choices, including Roma Old Town Wood-Fired Pizzeria, Oak Stone Craft Pizza & Bar, Umberto’s, Cafe Del Sol, and more. Look for veggie specialty pizzas or custom builds to fit your diet.
Can I get gluten-free pizza in Winchester, VA?
Yes, several local pizzerias serve gluten-free crusts. Try Oak Stone, Roma Old Town, Cafe Del Sol, and Firenza Pizza for tasty gluten-free pizzas that don’t compromise on flavor.
Which place is best for large pizza slices?
Benny Meleto’s is famous for slices so large you may need both hands. If you want a memorable size and plenty of flavor, this is the spot.
Who delivers pizza late at night?
Chain favorites like Domino’s Pizza, Pizza Hut, and Papa Johns offer late-night delivery. Some local places, like Roma Old Town Wood-Fired Pizzeria, may offer late service, especially on weekends. Always check hours before ordering.
Where can I find authentic wood-fired pizza?
Roma Old Town Wood-Fired Pizzeria and Alesatian Brewing Company are your go-to spots for authentic wood-fired pies with charred, flavorful crusts.
What’s the best pizza place for groups or parties?
Ledo Pizza is great for gatherings, with its variety and catering options. Many other spots, like Umberto’s and Paisano’s Pizza, are also group-friendly.