There’s something about pairing a young, acidic white wine with a briny oyster that has always been irresistible to me. Whether enjoying the combination at a local restaurant close to home or savoring it on a boat in Croatia’s Pelješac Peninsula, wine and oyster tastings are one of my favorite experiences to enjoy while on vacation.
This year we took a bit of a staycation to Virginia’s Chesapeake Bay Wine Trail for the 2018 Fall Oyster Crawl to learn about what makes our home state’s bivalve selection worth exploring. This article from Road Unraveled contributing writer Craig Mathias just might convince you to make Virginia your next wine and oyster destination!
– Stephanie
GUEST AUTHOR: Craig Mathias

I don’t remember the first raw clam or oyster that hit my tummy, but, oh my, that wasn’t the last. Sure, let’s go with phlemy texture, but I assure you the flavor is a whole ‘nother matter. Which brings me back to middle school, when my biology class made a field trip to the tidepools near Moss Beach, California to study hermit crabs and anemones and such, and one of the teachers cracked open a sea urchin and slurped it down. Such would be frowned upon today, of course, as the environment of these tidepools absolutely must be preserved. But the point I want to make here is what he said whilst slurping: “you can really taste the sea.” If this metaphor appeals to you, and you like movies, spend a couple of hours with The Hundred Foot Journey, a contemporary fairytale that features the above-mentioned sea urchins in a similar context near the beginning of the film.
That taste of the sea is precisely what we were seeking in our participation in this year’s Fall Oyster Crawl, which is organized by an informal alliance of wineries constituting the Chesapeake Bay Wine Trail. Virginia, as even this former Northern Californian must admit, is making a lot of really, really good wines in close to 300 wineries today. As might be surmised from the name of their association, the participating wineries noted above are in prime Virginia oyster country, so the promotional pairing here is obvious. And while some may argue for beer as the natural accompaniment for raw shellfish, a light and dry white wine is by far the best choice, with the acid of the wine (think: lemon) balancing the sweetness of the fruits of the sea. The annual Fall Oyster Crawl is constructed around perhaps one of the most irresistible two-fers possible.
More Information: ChesapeakeBayWineTrail.com
More Information: ChesapeakeBayWineTrail.com/events/fall-oyster-crawl-2018
Virginia and Oysters: A Perfect Pairing
Oysters have been associated with the very history of Virginia since well before the founding of the colony in 1609. They’re so significant that the official Virginia website has a ton of information on them, including this tidbit, a direct quote: “Virginia is the largest source of wild and farmed oysters in the United States.” I didn’t know that, or that there are eight different oyster regions in the Commonwealth, or that there are a variety of oyster festivals and even tours during the year. You can find a wide variety of oyster species (yes, the flavor does vary a bit among these) in a wide variety of cooked and raw forms (read on) in restaurants around Virginia, but it’s undeniable that being as close to the source as possible is a really good idea. Chesapeake Bay is enormous, so truly dedicated oyster seekers could spend way more than the one day we had to dig in (poor attempt at oyster humor; please ignore).
If you’re looking for more information on the impact and status of Oysters in the Chesapeake Bay region of Virginia, take a look at this video.
Virginia Wine and Oysters: Another Perfect Pairing
We were able to visit only three of the eight participating wineries this year because one simply must invest a bit of time in a wine tasting at each winery visited, and, as good as the oyster delights are, one will get full after a while.
If you’ve not been to a wine tasting, a winery will generally offer a sampling of the wines they offer, usually a pour of about a half-ounce each. Many wineries offer between five and ten pours, and sometimes more depending on the size, production, and types of varietals they grow. Yes, the alcohol will build up in your system after a while, so a designated driver is a must. And, of course, since the unifying theme here is oysters, each winery offered a selection of tasty oyster samplings. Expect to pay around $10-15 for a wine tasting, and the oyster dishes are additional but reasonably priced.
Good Luck Cellars

The oysters here were provided by The Great Wicomico Oyster Company, who are primarily oyster farmers and wholesalers. They did, however, put together a great field kitchen at Good Luck Cellars, and we enjoyed some terrific raw oysters on the half shell – for only $1 each! – along with some absolutely delightful fried oyster tacos (in my experience, it’s difficult to get the frying right to avoiding overcooking, and our oysters were perfectly prepared). Freshly-opened raw oysters can be enjoyed plain, with a vinaigrette or mignonette, with cocktail sauce, or with a bit of lemon—and, of course, the above-noted Chardonnay. Non-oyster eaters (hopefully, this article will reduce that population) had access to crab balls, hush puppies, and more, all of which were excellent. Five stars all around – and I’d be back in a minute if such were possible.
More Information: GoodLuckCellars.com
More Information: GreatWicomicoOyster.com
General’s Ridge Vineyards

And returning to our oysters, we tried an interesting rendition of the classic Oysters Rockefeller and one I’ve not tried (or even heard of) before, Oysters Cackalacky, both provided by Denson’s Grocery. Both of these are grilled; the Rockefeller variety featured spinach, mornay, and shredded cheese, while the Cackalacky version had toppings including a fairly mild hot sauce, celery, and bleu cheese—perhaps best described as Buffalo wings meets oysters. Both were great, although I did detect an occasional grain of sand, which is to be expected. Anyway – it’s remarkable how tough and heavy an oyster shell is – this is a clue as to just how valuable the contents really are (or, in our case, were).
More Information: GeneralsRidgevineyard.com
More Information: DensonsGrocery.com
Ingleside Vineyards

As for oysters at Ingleside, it was Denson’s to the rescue once again, this time with grilled Oysters Denson, seasoned and topped with parmesan cheese – and just as delightful as the Oysters Rockafeller and Cackalacky we enjoyed at General’s Ridge. We completed the day with perhaps the best chocolate éclair I’ve ever had. And yes, there are indeed desert wines that would pair well even with that. But it was, sadly, getting dark, a bit cold, and time to call it quits for this year.
More Information: InglesideVineyards.com
Experience the Fall Oyster Crawl!
Some unsolicited advice: mark your calendar for the Chesapeake Bay Wine Trail Fall Oyster Crawl next year, as we already have. There were wineries (and oysters) we clearly missed this go-round, and there are more oysters (and wineries) yet to try. If you’re new (or not) to wine, try a tasting, and if you’re new (or, again, not) to oysters, this is one event not to be missed. Regardless, be prepared for a very enjoyable day with two of the best that nature has to offer.
Have you tried Virginia oysters? Leave a comment below a let us know your favorite spots to enjoy them- and the Virginia wine with which you pair them!
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* From time to time, our travels are directly impacted by a service or company. This post includes our candid review of our experiences at various locations in Virginia. We selected these locations based on our own research and travel needs; we were not offered and did not receive compensation of any kind from them or any other party in exchange for our review. Learn more about our travel philosophy here.