Culinary Road Trip Through Charlottesville: Be Sure to Pack a Cooler

by Fayeruz Regan 03.2023

As we wound up the mountaintop, we reached the monastery just in time to meet the sisters. They sold us the creamiest wheel of gouda I’ve ever had. Charlottesville is widely regarded as Virginia’s wine country, but what’s lesser known is that the region is positively studded with culinary gems, all worth the drive.

Some stops are leisurely, where you can enjoy a meal by a roaring fire. Other places sell must-have products that will bring joy to your meals. Below, I’ve listed the must-stop places. Come hungry and pack a cooler.

Our Lady of the Angels Monastery

For over 30 years, these nuns have perfected the art of making Gouda cheese with milk from grass-fed cows. Using old world techniques from the Netherlands, the result is buttery and delectable. Their Gouda is sold daily from 2 till 4 pm, except on Sundays. Part of the excitement is getting there, with a winding mountain road offering sweeping views...without a guardrail.

Olamonsastery.org - 3365 Monastery Drive Crozet, VA 22932-2116 – (434) 823-1452

Greenwood Grocery

This destination location has been lauded in Southern Living, among other publications. Imagine a rustic cabin surrounded by pottery, statuary, and outdoor living oddities. Then upon entering, a sprawling selection of local wines and international foods sits on vintage wooden shelves and wicker baskets. View the old-fashioned candies and pour yourself a fresh cup of coffee, which is still only a dollar. Best of all, Greenwood Grocery makes fresh sandwiches and sides on-site. The Melrose is to die for: Homemade pimiento cheese, roasted portabella mushrooms and grilled onions on country bread so buttery and toasty, I can still hear the crunch.  

Greenwoodva.shop - 6701 Rockfish Gap Turnpike, Crozet, VA 22932 - (540) 456-6431

Pippin Hill Winery

There is no shortage of options in Virginia’s wine country, but Pippin Hill is a standout. They have no ordinary tasting room, but a tasting room that offers pairings with gourmet cuisine. Much of their produce is supplied by their farm, making it a true farm-to-table experience. But most of all, the wine is delectable. Stock up on their merlot.

Pippinhillfarm.com 5022 Plank Rd North Garden, Virginia 22959 - (434) 202-8063

Dr. Ho’s Humble Pie

Two minutes down the road from Pippin Hill is Dr. Ho’s Humble Pie. Their homemade ranch dressing became so popular, that they now sell mason jars of it. Grab the largest size – you’ll regret it if you don’t. It’s creamy, herbal, and tastes as if there’s a hint of Parmesan.  And if Dr. Ho’s happens to have their pots de crème packaged to go, grab one of those too. Make room in your cooler for the ranch, but don’t postpone joy on those pots de crème. They are so rich and chocolatey, you’ll eat it with your eyes closed. And if you happen to be hungry, this hippie-themed hangout is known for “alternative” pizzas and myriad munchies in between.

www.drhoshumblepie.com - (434) 245–0000 - 4916 Plank Rd, North Garden, VA 22920

Basic Necessities

Basic Necessities sounds like a place to grab eggs or paper towels, but the reality is far from it. This quaint cottage with a country garden is a gourmet shop, filled with wine and cheese. And if you step into the back, an offbeat cafe awaits, with wraparound windows, a roaring fireplace, and curated art. Settle in for the type of cozy experience that allows you to live in the moment. It’s a feast for the eyes. When we ordered brunch, we were all surprised with an amuse-bouche of poached fruit with cinnamon granola and fresh cream. The food is locally-sourced, often organic, and you always seem to smell roasted garlic and baked bread upon entering. On your way out, stock up on local cheese and a bottle or two of wine.

basicnecessities.us 2226 Rockfish Valley Highway Nellysford, VA 22958 (434)361-1766

By this time, your cooler is filled to the brim, and wine bottles are clanging. This is the sound of a successful hunt. One may not consider this road trip a hunt with me pointing the way, but you never know what you’ll find at these locally-owned businesses. It depends on what’s in season, what’s just been corked, what mood the chef was in.

Either way, when you get home and unpack your haul, you’re infusing new flavors into your kitchen, and a little vitality into your life.

Bon appetit.