Introduction

It was a crisp autumn afternoon when I first rolled up the winding drive to Pippin Hill Farm & Vineyards, my windows down and the scent of turned earth and wildflowers on the breeze. I remember thinking, “This… this is what people mean when they talk about Virginia wine country.” That day started with a glass of their Viognier and ended with a sunset so stunning I forgot to finish my chocolate budino. (Don’t worry—I went back for it the next week.)

For those of us lucky enough to live near Charlottesville and the Monticello Wine Trail, Pippin Hill isn’t just a winery—it’s a way of life. Located off Route 151, a scenic stretch that cuts through the foothills of the Blue Ridge Mountains, this spot is a magnet for locals and travelers alike. It’s racked up a slew of awards, including a Wine & Spirits Top 100 Winery distinction and countless accolades for its venue, hospitality, and food. But for me, it’s personal—it’s the place I go to celebrate, to unwind, to show off what Virginia wine can do.

History and Background

Pippin Hill opened its doors in 2011, the brainchild of owners Dean and Lynn Andrews. Dean’s background in high-end hospitality and Lynn’s flair for event design fused into something magical: a vineyard experience that’s as much about elegance as it is about authenticity. They didn’t want to recreate Napa. They wanted to elevate Virginia.

They faced the usual hurdles—tricky weather, skeptical wine critics, and the challenges of opening a full-scale event venue that also operates as a working farm and vineyard. But they stuck to their vision: sustainability, local sourcing, and the marriage of culinary excellence with boutique wine production. Over the years, they’ve built a team of experts, including head winemaker Michael Shaps, whose influence and skill have raised the bar for the entire region.

The Production Process

Let’s talk terroir. Pippin Hill sits in the Monticello AVA, a place Thomas Jefferson once dreamt would rival Europe. The soil here—clay-rich and well-drained—combined with warm days and cool nights, is perfect for varietals like Viognier, Cabernet Franc, Petit Verdot, and Chardonnay.

What makes Pippin’s wines stand out is their balance. Take their 2022 Sauvignon Blanc—it’s all citrus and minerality, with a clean finish that begs for seafood. Or the 2019 Easton Blue, a Bordeaux-style blend that’s lush with black cherry and hints of cedar. I brought a bottle of that to my cousin’s rehearsal dinner, and it was gone before the chicken hit the table.

The team practices thoughtful viticulture: cover cropping, hand-picking, and small-batch fermentation. The winemaking space is sleek, temperature-controlled, and visible from the tasting room—so you can sip while watching the magic happen.

Wines of Note

Here are a few standouts you should try:

• Viognier (2021) – $32/bottle

  Aromatic and floral, with notes of honeysuckle, white peach, and melon. Perfect with goat cheese or spicy shrimp.

• Petit Verdot (2019) – $42/bottle

  Deep purple, full-bodied, with flavors of blackberry, black pepper, and a velvety finish. Ideal for a cold night by the fire.

• Zero White (Non-Vintage) – $28/bottle

  A lower-alcohol white wine with subtle pear and citrus. Great for daytime sipping.

• Easton Blue (2019) – $56/bottle

  Their flagship red blend. Complex, aged in oak, and totally worth cellaring.

Dining at Pippin Hill

You know those places where the food feels like it was made just for the moment you’re in? That’s what dining at Pippin Hill is like. It’s not just a bonus to the wine experience—it’s a major part of why people (including me) keep coming back.

The Tasting Room Menu is built around what’s fresh and seasonal. They’ve got their own culinary garden just steps from the kitchen, so the greens on your plate were probably snipped that morning. It’s the kind of place where you’ll find elevated small plates that still feel soulful. Think crispy polenta topped with wild mushrooms and shaved Parmesan, or grilled local peaches served with ricotta and honey from nearby hives. It’s farm-to-table in the truest sense—clean, honest flavors, rooted in Virginia’s bounty.

A few highlights from recent visits:

• Cheese & Charcuterie Board: Locally-sourced cheeses (Meadow Creek Dairy is a regular), artisan-cured meats, housemade pickles, honeycomb, and toasted sourdough. It’s beautifully plated and ideal for sharing.

• Shrimp & Grits: A southern classic reimagined—creamy stone-ground grits, perfectly spiced andouille sausage, and plump, garlicky shrimp.

• Bibb Lettuce Salad: Tossed with herbs, candied pecans, and a tangy buttermilk vinaigrette—it’s light, crisp, and pairs beautifully with their Sauvignon Blanc.

• Lamb Meatballs: Rich, spiced, and served with a yogurt drizzle and grilled flatbread—a savory favorite with the Cabernet Franc.

And the desserts? Chef Ian Rynecki makes sure the finish is just as strong as the start. The chocolate budino with olive oil and sea salt is decadent but never too sweet, and the rotating seasonal tarts (fig and almond, anyone?) are a total treat.

You can enjoy your meal in the Tasting Room, on the covered veranda with sweeping views, or out on the lawn with a picnic-style setup. Pro tip: grab a bottle and a blanket, and head to one of the Adirondack chairs scattered across the lawn. That’s how I do it on lazy Sunday afternoons.

Events

There’s always something going on here:

• Vineyard Walks & Tastings: Educational and gorgeous.

• Wine Pairing Dinners: Seasonal, reservation-only events with multi-course menus.

• Live Music Saturdays: Grab a glass, find a spot on the lawn, and relax to local tunes.

• Workshops: Flower arranging, seasonal cooking classes, and more.

And if you’re thinking about tying the knot? This is the place to do it. Their event barn and verandas have hosted countless weddings, each one stunning in its own way. (My best friend got married there and had a sunset ceremony that looked like a movie scene.)

Visitor Experience

From the moment you step onto the property, you feel it—this place has presence. There’s something about the way the Blue Ridge Mountains unfurl in the background, the tidy rows of vines catching the sunlight, and the smell of lavender and fresh bread wafting through the air. It’s elegant, but not fussy. Sophisticated, but still relaxed. Like your cool friend who also knows how to host a killer dinner party.

The Tasting Room is stunning—airy, rustic-chic, and full of light. Picture high ceilings with exposed beams, warm wood finishes, and iron chandeliers. Floor-to-ceiling windows let in the natural light and frame postcard-worthy views. There’s a large fireplace in winter that gives the space a cozy, fireside lounge vibe. You’ll often see couples clinking glasses in one corner while a group celebrates a birthday in another.

Outside, the veranda is the prime seating spot for good weather—shaded, breezy, and framed by flowering plants and stone walls. On the lawn, Adirondack chairs are perfectly positioned for lounging with a bottle, and guests are encouraged to roam, relax, and soak in the scenery. On weekends, the energy buzzes a bit more—live acoustic music, laughter from a nearby bridal shower, maybe even a golden retriever lying in the grass while its humans sip rosé nearby.

You can book:

• Classic Tastings: A curated flight of their signature wines, guided by friendly, knowledgeable staff.

• Private Tastings & Vineyard Tours: For a more in-depth experience (ideal for wine nerds like me).

• Table Reservations: Especially helpful for dining during lunch hours or peak weekends.

• Workshops: Seasonal events like wine blending, cooking classes, and even flower arranging.

Accessibility is thoughtfully considered. There’s ample parking, ramp access to all key areas, and staff happy to accommodate special needs. Kids are welcome, though this is definitely a grown-up-friendly experience. Dogs? Absolutely, as long as they’re leashed and well-behaved—they’re welcome on the lawn and veranda.

Every visit feels a little different. Sometimes I’m in and out with a few bottles for the weekend. Other times, I stay for hours, losing track of time as the light changes across the hills. Whether you come with friends or fly solo, Pippin Hill has a way of making everyone feel like they belong—glass in hand, heart full, and already planning the next trip back.