Exploring the Wine Country, of Virginia
Time for a clarification already: the entire state of Virginia supports grapes and features wineries, so when I talk about "wine country" I'm talking generally about the wineries in the Monticello American Viticultural Area (MAVA) of central Virginia between Charlottesville and Staunton. This is the area in which Thomas Jefferson initiated the phenomenon of American wine, arguably making the MAVA the grandfather of California's wine country.
Within the MAVA are at least 33 wineries that meet the requirements for inclusion on the Monticello Wine Trail list. And in case you want some variety, there are also numerous breweries, some distilleries, and a handful of cideries. There are also two excellent pizzerias--one of which was named the best in Virginia, while locals will tell you the other is just as good or better. Oh, and if you need a day to rest your liver, Virginia's wine country is situated in one of the most historic areas of the country with Monticello, Ash Lawn, UVA and innumerable "lesser" historic sites right there.
Planning your Trip
Finding wine country is easy, finding your way around wine country is a little tougher. The fact that many of Virginia's roads started as animal paths that were made into horse trails that became wagon roads that became paved roads results in a meandering spider-web of traffic flow. If you're used to Phoenix's grid pattern you'll leave Virginia with a new appreciation for our city planners...and if you're used to the east coasts haphazard road planning then, well, you don't have any real navigational advantage. When you combine winding roads that follow no obvious plan with tours of wineries miles apart you end up with an absolute requirement for a DD or a tour driver because Uber or Lyft aren't viable options and driving drunk never is. Pad your schedule with plenty of time for driving because there is frequently a 15-30 minute drive between locations.
Another difficult logistical hurdle is the fact that Virginia packs 95 counties into its borders, each full of cities, towns, and neighborhoods, which will keep you on your toes when choosing lodging--"Hmm...is North Garden near Crozet or Afton...?" What we ended up doing was locating a cluster of wineries/breweries that we absolutely wanted to visit and used one of them as the anchor for figuring out distances and drive times from lodging. After using this method, we did a general geographic search for hotels/AirBnBs and narrowed down the search. If you start with Charlottesville then move your map to where the alcohol is then you'll be good to go.
Depending on where you find to stay there might not be many dining options in the neighborhood. We were lucky enough to have one of the two best pizza places in the region a couple minutes away, but aside from that the nearest non-winery restaurant was easily 30 minutes away. Grocery stores weren't any closer. This didn't stop us from having great meals, we just had to be more deliberate about our grocery shopping and planning our restaurant outings. Don't let this dissuade you, just don't show up unprepared.
Pippin Hill - Pippin is the most grand vineyard and winery that we saw in the area. The tasting room/restaurant is situated on a ridge top giving sweeping views of the valley below and grape rows. Built in an ultra chic farmhouse style, this is the kind of place that lets you forget everything outside the property. Unfortunately, my ability to describe wine is limited to red, white, good, bad, so this isn't the place to get tasting notes, but suffice to say it was quite enjoyable and paired well with the lunch menu. Long story short, go for the setting because everything else lives up to its standard. Suggested wine: we enjoyed the viognier (which is Virginia's signature wine grape).
King Family Vineyards - The only vineyard with a polo ground on the property, so you know its posh. They also have a selection of cheeses, meats, and crackers (I recommend the lemon goat cheese). The tasting room itself is well decorated though lacks some of the character of Pippin or Veritas. But much like a hotel room in Vegas, if you're going for the decor you're missing the point. All of the whites were delicious and I still regret not buying a bottle of the viognier. Suggested wine: Roseland or Viognier.
Afton Mountain Vineyards - "good wine doesn't grow in ugly places" is easily the best slogan of any winery I've visited, and it holds true. Whether its the lake to the left, the sweeping vineyards to the right, or the mountains in the background, you won't be disappointed looking in any direction. Unique among all vineyards that we visited, Afton Mountain has several cabins on site to rent so you don't have a long trip after enjoying the tasting room. No food was available here, so plan accordingly. Suggested wine: we enjoyed the rose.
Veritas Vineyard & Winery - this one sets itself apart with a tasting room reminiscent of a hunting lodge with exposed wood, leather furniture, and a large fireplace. They offer two tasting flights, I recommend both. Food is available or bring your own picnic to enjoy around the grounds. Suggested wine: honestly, this was the last stop of the day and I called grape vines "wine trees," so my recommendation is a little suspect, but I think it was the Petit Manseng.
Starr Hill Brewery
Dr. Ho's Pizza
Albemarle Cider Works
(rooftop restaurant in Crozet)