Where We've Been: A Few Days in Virginia Wine Country
The leaves were at peak, the cell service dropped out somewhere on the drive down (no complaints here), and a couple of days in Virginia wine country just outside Charlottesville were exactly what I needed.
Checking In at Crossroads Inn
Home base was Crossroads Inn in North Garden, the historic inn that Lynn Easton and Dean Andrews, the husband-and-wife team behind the Easton Porter Group, bought in 2022, right next door to their Pippin Hill Farm & Vineyards. I was greeted by beautiful gardens and the sound of chickens clucking in the background, and waiting in my room was a spread of Virginia-made snacks, kettle corn, peanut brittle and apple cider donuts, which are my kryptonite. A little walk led me straight to said chickens, and I tried to feed them ... I did my best.
Jazz and Wine on the Downtown Mall
A quick change and a quick ride into downtown Charlottesville, where we wandered the Downtown Mall and ducked into Rapture, a darling little spot for a glass of wine and some live jazz.
Dinner at Aster
Then off to Aster, the newish restaurant that opened in May in the Glass Building, just a couple of blocks from the Mall. Getting in the door has a little speakeasy fun to it, and inside, the dining room is all cozy library vibes, with a peek into the open kitchen. Chef Drew Dunston, who cooked at Acadia and Marigold by Jean-Georges, builds his menu around whatever Virginia farms like Peaceful Heart Farm and Shenandoah Sky Ranch are bringing in, then borrows from Japanese, Scandinavian and French kitchens to finish the plates. Let sommelier Caleb Russell pick your pour.
There was nothing on the menu I didn't want to order. We started with the Salt Risen Potato Bread with local butter, plus Virginia cheeses and Lady Edison ham. Our server told us we could not miss the Cornflake Fried Chicken, juicy Joyce Farms chicken thighs in a shatteringly crisp cornflake crust with a gochu hot sauce. A fall citrus salad graced our table (I can never pass one up), and the cavatelli dumpling, stuffed with North Carolina shrimp with shiso in a sauce spiked with Calabrian chili and lime.
Back to Crossroads Inn to get snuggled in for the night. (It was also election night, so you know I did not get to bed early!)
A Day at Pippin Hill Farm & Vineyards
Morning greeted us with a beautiful day, lush landscaping wrapping around the Inn and a gorgeous breakfast buffet laid out, featuring, of course, eggs from the very chickens I tried to feed the day before.
Then on to Pippin Hill, which Lynn and Dean opened back in 2010 and is now one of the stops on the Monticello Wine Trail. The architecture takes its cue from an old Virginia barn, but inside it's all polish, the tasting room bar is built from reclaimed cypress, The Granary hosts the big (BIG) weddings and parties, and out on the stone terrace the Blue Ridge Mountains stretch out in front of you.
We were greeted with a glass of bubbles and set off on a fantastic tour with our guide, Matt Harmon, learning all about the vines, the grapes and the gardens planted throughout the property. Under renowned winemaker Michael Shaps, the vineyards produce up to 64 tons of grapes a year across 16 varietals, from classic European grapes to historic ones first championed by Thomas Jefferson. Then we wandered the kitchen garden, which Head Gardener Celina DeBrito plans hand in hand with the chefs, terraced rows of vegetables and herbs (plus a coop full of chickens) that turn up on the plates that very day. We all gushed over the cucamelons, tiny fruits that look like baby watermelons but taste like a cross between a cucumber and a melon, and the kitchen pickles them too.
The Tasting
After our garden education, we headed in for a wine tasting, with Matt walking us through each pour, and Chef Victoria created a paired menu to go with every wine. The 2025 Viognier, Virginia's state grape partnered with the Green Apple Zeppole from there we moved through the 2023 Sauvignon Blanc and on to the 2021 Hillside White. I was a huge fan of the 2019 Wild Acre, a blend of Merlot, Tannat and Cabernet Sauvignon, that came paired with a creamy deviled quail egg with topped with chorizo and a dropper filled with house-made hot sauce. The rest of my crew fell for the 2021 Ridge Reserve, a Cabernet Franc and Malbec blend that took gold at the American Fine Wine Competition.
Lunch at Pippin Hill
As if we needed more, we sat down to lunch, crispy Brussels sprouts, caramelized carrots over whipped pecan butter with puffed farro and, of course, a little more wine. Then Chef Victoria stopped by our table with a bowl of those pickled cucamelons, and they are officially my new favorite bar snack. A special thanks to Executive Chef Victoria Cosner for laying out such a feast, and to Matt, who navigated us through the day and filled it with stories about the wine and the winery.
Sunset Cooking Class with Chef Victoria Cosner
After a little break, back we went to the winery, where Chef Victoria hosts her cooking classes. A Charlottesville native, she started at Pippin Hill as a prep cook in 2015 and worked her way up to lead the kitchen, and this year she was named 2026 Chef of the Year at the Virginia Restaurant, Lodging & Travel Association's Ordinary Awards.
We watched a gorgeous sunset and then headed into the massive kitchen, where this was no sit-back-and-watch class. Chef Victoria and her team first demoed her Louisiana-themed feast, and then we were put to work making our own dinner, stirring a roux, chopping the holy trinity, gently folding in the shrimp and crawfish for our étouffée and topping it all with lump crab at the end.
Then Chef announced, "Work for your dessert!" Not really, but we did. So we bloomed the yeast, folded the dough and deep-fried our own beignets (the trick is to powder them immediately). Chef Victoria is a very patient teacher, and cooking side by side with new friends was such a fun way to spend the evening. Afterward we sat down to eat everything we'd made, even though we were already stuffed.
One More Morning
A restful night's sleep in the comfy bed, and come morning I had to have one of those hard-boiled eggs, the yolks so jammy because the eggs had literally come from the chickens that morning. Then back in the car and on my way home. An easy and wonderful little getaway to Virginia wine country.
If You Go
Crossroads Inn, North Garden, Va. · crossroadsinn.com
Pippin Hill Farm & Vineyards, North Garden, Va. Tastings, garden strolls, Vintner's Table pairings and cooking classes with Chef Victoria · pippinhillfarm.com
Rapture, 303 E. Main St., Downtown Mall, Charlottesville
Aster, 313 Second St. SE, Suite 105, Charlottesville · Dinner Tuesday through Saturday from 5 p.m. · (434) 906-7424 · astercville.com