If you want to enjoy a glass of local wine while your kids have some pizza, you don’t need to travel far in Northern Virginia. The Virginia wine country surrounding Middleburg offers more than just stunning views and award-winning wines. Some nearby wineries also serve tasty pizza in family-friendly settings, making them perfect for a relaxed day out with the kids. With options like gluten-free pizza and farm-to-table meals, here are two of our favorite places where everyone can enjoy sipping, snacking, and unwinding together.
Nestled in the heart of Virginia’s Hunt Country, Middleburg is the perfect countryside escape within easy reach of the D.C. metro area. It’s located about 60–65 minutes from Washington, D.C., 35 minutes from Dulles International Airport, 25 minutes from Leesburg, and 30 minutes from Ashburn, making it an ideal destination for day trips or relaxed weekend outings. Known as the Nation’s Horse and Hunt Capital, Middleburg blends historic charm with rolling vineyards, luxury inns, and equestrian culture, offering visitors a timeless mix of wine country elegance and rural Virginia heritage.
Chrysalis Vineyards at The Ag District
Tacked in the heart of Middleburg, Chrysalis Vineyards makes it easy to slow down for an afternoon. Families spread out at picnic tables, kids enjoy a casual lunch (with adult supervision, as required), and dogs lounge nearby in the shaded outdoor areas. It’s the kind of spot that keeps things simple: great wine, freshly made food, and a warm sense of hospitality. In the colder months, the spacious outdoor seating with multiple fire-pit tables makes it especially cozy, offering plenty of room to unwind while taking in the vineyard views.
The menu features 14- to 16-inch pizzas crafted with “The Monk” mozzarella made exclusively by Locksley Farmstead Cheeses – a working creamery that Chrysalis owns and operates. The cheese is made from milk produced on their own farm, which makes them a true farm-to-table location that sets them apart.
You can enjoy the full menu, including eight signature pizza varieties offered with either red or white sauce options including Margherita, Basil Pesto, Classic Cheese, Hot Italian, Bacon Gouda, Meat Lovers, Classic Pepperoni and Alsatian. A gluten-free cauliflower crust is available for a small up-charge, making it easy for everyone at the table to enjoy a slice.
Cana Vineyards & Winery
Just across the street, Chrysalis Vineyards offers a relaxed, welcoming atmosphere where you can easily unwind for an afternoon. Families spread out across the property—whether on the open-air patios or in the covered pavilion with its large fireplace, a favorite gathering spot in cooler months—where dogs are also welcome. Kids enjoy slices of pizza while dogs rest comfortably under the tables, creating an easygoing, everyone-belongs-here kind of environment.
The winery keeps its menu simple and well-crafted, offering four freshly made 10″ New York–style pizzas from the Black Oak Café. Guests can choose from the Three Cheese, made with red sauce, asiago, mozzarella, and provolone; the Pepperoni, featuring red sauce, asiago, mozzarella, provolone, and cup pepperoni; the Margherita, topped with red sauce, fresh mozzarella, basil, and parmigiano; and the Wild Mushroom & Onion, a rich blend of garlic cream sauce, mozzarella, provolone, cremini mushrooms, and caramelized onions. Each pie is baked fresh on the hilltop and pairs perfectly with a glass of wine.
The café serves Italian gelato, espresso drinks, charcuterie, and snacks, making it a favorite with both kids and parents. Families can spread out across the outdoor patio or settle in by one of the many fire pits to enjoy the views with a warm drink in hand. Dogs are welcome outside and in the covered pavilion with the large fireplace, giving families plenty of flexible seating options where everyone—kids, pets, and adults—can stay together. On weekends, live music adds to the relaxed atmosphere, while the cozy indoor fireplace makes it a perfect place to warm up after a stroll by the vines.
“While you are here“ – explore more of Middleburg
If you’re heading into town after your winery visit, Middleburg has a couple of charming family-friendly stops worth exploring. Stitch Middleburg is a cozy needlework and craft shop offering modern stitching kits, tools, and handmade gifts—an inviting spot for kids and adults who enjoy anything creative. Just a short walk away, Every Little Something offers a beautifully curated mix of stationery, art supplies, screen-free kids’ activities, and unique gifts. Both shops are perfect for rounding out the afternoon, giving families a relaxed way to browse, unwind, and enjoy a little more of Middleburg’s small-town charm.
Tips for Enjoying Your Visit with Kids
- Check the event schedule, or sign up to get events delivered to your mailbox. Many wineries offer seasonal events like live music, harvest festivals, and holiday markets. Visit their websites before your trip to make sure events are family-friendly.
- Bring the pup. Both Chrysalis and Cana welcome dogs in outdoor spaces, so your furry friend can join in the fun.
- Pack for the weather. November can be brisk, especially in the evenings. Dress in layers, bring a blanket for outdoor seating, and take advantage of indoor fireplaces when you need to warm up.
Whether you’re sipping wine by the fire or enjoying pizza and gelato with the kids, these two wineries near Middleburg are perfect for a relaxed, family-friendly day out. So grab your loved ones, bundle up, and experience the best of Virginia’s wine country together.
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