Culinary Getaway at Pippin Hill and Crossroads Inn

Between the culinary classes, guided wine tastings, and lush landscapes outside the tasting room’s windows, it’s easy to see why Pippin Hill — situated on the Monticello Wine Trail, a 15-minute drive from downtown Charlottesville — is a sought-after culinary destination.

What turns it into a full-fledged gourmand getaway is a stay at their sister property next door, the historic Crossroads Inn, where you’re treated to farm-fresh, home-cooked breakfasts and four-course dinners. The way that food and wine converge at both properties, mirroring the growing and harvesting seasons, is a potent reminder of what makes an ideal pairing: What grows together goes together.

Executive Chef Victoria Cosner is the creative force behind the culinary classes and tasting room restaurant menu’s garden-to-table approach. The 41-acre organic garden, overseen by Head Gardener Celina DeBrito, produces seasonal produce such as herbs, leafy greens, lettuces, tomatoes, squash, and peppers and includes a chicken coop and apiary, too. Outside of winter months, classes include a garden tour, during which Cosner encourages picking and snacking.

The wood-fired pizza class is particularly fun, especially getting to stretch the dough and choosing from an entire table dedicated to toppings, including specialty ingredients like cured egg yolk for a pop of richness and saltiness and spicy honey for a kicky, sweet finish.

Whether post-culinary class or tasting room visit, retreat down the hill to Crossroads Inn, a designated Virginia Historic Landmark that is also listed on the National Register of Historic Places. Originally, the Crossroads Tavern served as a tavern and overnight lodging for travelers and farmers using the Staunton and James River Turnpike. The road was an essential way for growers to get their goods — such as flour, oats, corn, salt, bacon, and whiskey — across the Blue Ridge Mountains. These days, the inn has upgraded its accommodations to include modern amenities, like high-quality bedding and linens, cozy bathrobes, local chocolate from Charlottesville purveyor Chocolatesville, and Nespresso machines with a robust assortment of coffee pods. However, its historic charm remains.

There are stories associated with every room and whispers of history around every corner. The Dabney Carr room — named for Judge Dabney Carr, Thomas Jefferson’s nephew — was also a private dining room in which Thomas Jefferson held a meeting with Martin Van Buren in 1824. The Roosevelt Suite pays homage to Theodore Roosevelt’s visit, which included dinner at the tavern after a day of birding while visiting Pine Knot, his and Edith Roosevelt’s nature and family retreat in southern Albemarle County. And the Travelers Suite, once dubbed the Innkeeper Suite, was where the original owners and their 17 children lived while operating the inn.

The Pippin Cottage, just opposite the main house, was the original bakehouse, smokehouse, and summer kitchen — which explains the extra-large fireplace on the lower level — that’s now outfitted with a kitchenette and living area and makes for a more private stay. The upstairs level, which houses a queen-sized bed and bathroom, was added later, utilizing some of the original wooden beams from the lower level to construct the ceiling and roof supports. In 2022, the inn was purchased by Pippin Hill Farm & Vineyards’ owners, Dean Andrews and Lynn Easton, the hospitality pros behind Easton Porter Group, giving the inn and cottage a design refresh while preserving its structural integrity. 

Breakfast is served in the former tavern dining room, where you’ll be warmly greeted by Innkeeper and Chef Joe Koscielniak. He’ll offer you juice and announce the morning’s menu, typically a baked good, like tender cinnamon rolls or apple turnovers, a biscuit or English muffin with flavored butter, fruit, and an egg dish, like a frittata made with fresh eggs from the onsite flock and herbs picked from the chef’s garden just outside, paired with diced potatoes and crispy strips of bacon. To caffeinate, there’s a self-serve coffee bar with a pot of freshly brewed, strong coffee and a nice assortment of loose-leaf teas. The hearty breakfast will set you up for the day ahead, whether your plans include exploring the vines or cozying up in your room. 

In the evenings, the dining room doubles as a communal room, where guests often hang out with books or games — unless it’s a Friday night, when the “chef’s table in the tavern” experience cues a seasonal, four-course dinner with wine pairings. What’s especially unique about these pairings is that Koscielniak incorporates wines into each of the dishes, in addition to glasses of wines for sipping.

He’s fond of pairing viognier with sweet and smoky dishes, like a bean soup with a terrific kick, owing to the addition of a few drops of Tabasco and toasted cracked black pepper. Steamed vegetables often benefit from a splash of white wine, like a recent dish of green beans paired with pan-roasted sea bass with charred garden-herb vinaigrette, while coffee-braised short ribs get a lift from Bundoran Blue — a merlot, petit verdot, and cabernet franc blend — which also plays off a side of creamy truffle mashed potatoes superbly.

You’ll also have ample opportunities for sampling delectable wine and food pairings in the tasting room. Sign up for an estate tour and tasting for an up-close look at the vines and gardens. Grapes grown here are made into wines by venerated winemaker Michael Shaps of Michael Shaps Winery, including Pippin Hill’s zippy sauvignon blancs, complex cabernet francs, and barrel-fermented chardonnays. What’s especially cool about the guided wine tasting is that each of the six pours are paired with bites crafted by Cosner. Food offers another entry point from which to understand the wines, whether you want to deepen your knowledge or learn how to taste wines for maximum appreciation.

Assistant Tasting Room Manager Carter Mace was on hand, noting that the best pairings employ both complementary and counter flavors and characteristics, like a bright and lively 2023 chardonnay accompanied by a delicate pecan macaron, whose richness played off the wine’s acidity, while the sweet apple buttercream filling brought out the wine’s apple and stone fruit notes.

Tastings conclude with a full pour of your choice and a reserved table in the tasting room, where you can order cheese and charcuterie boards, along with gourmet small plates and shareable dishes a la carte. I paired a glass of petit verdot with tagliatelle tossed with butternut squash and pancetta in a brown butter beurre blanc, alongside the tasting room’s beloved flash-fried Brussels sprouts plated with charred shallot and miso glaze, tahini stracciatella, and tobacco onions. From my seat at a two-top table near the window, I took in the sweeping views of the vineyard and the Blue Ridge Mountains beyond, a lovely backdrop to deepen my appreciation for the stories and tastes of the land before me.