Dining (and Wining) in the Moonlight

Savoring expert food pairings and a spectacular setting at an Upper Shirley vintner’s dinner.

Photography by Tyler Darden

On a brisk Friday night in October, 70 guests sip glasses of Viognier and untie neat brown boxes at one long table, a stone’s throw away from the James River, perpendicular to and centered on Upper Shirley Vineyards’ Low Country-style white-clapboard winery—good feng shui. It’s too windy to light the candles in the silver candelabra, but strings of bistro lights twinkle overhead, and the mood at this much-anticipated four-course, five-wine alfresco dinner is electric anyway. Guests, most of whom did not know each other before, laugh and exchange stories, giddy for the feast they are about to receive.

Inside each box, they find three petite biscuits—buttermilk, squid ink, and roasted beet—paired respectively with flavored butters of pimento cheese, anchovy, and honey. It’s just the first revelation of chef de cuisine Ernie LaBrecque’s tour de force meal that has been weeks in the making. No, make that years.

All or Nothing

Three years after opening its doors and six since the first vines were planted, the winery, 20 miles east of Richmond, now hosts more than 25 weddings a year, monthly prix-fixe wine-paired dinners, live music on weekends, and daily tastings of the vineyard’s critically acclaimed wines. Stop by on a sunny summer weekend and you’ll find the tasting bar three deep, a singer-songwriter outside surrounded by appreciative fans, and the tables inside and out filled with diners sipping iced tea and rosé, and noshing on charcuterie, lobster hushpuppies, and shrimp and grits. 

“We have created a destination spot and made this farm relevant, a place that can prosper and thrive,” says Tayloe Dameron, who together with his wife, Suzy, owns the winery. A Virginia native and former Wall Street bond trader, Tayloe is known for his acerbic wit and sideburns to match, and now more and more for his prowess at growing grapes. “I’m a passionate advocate of Virginia wine. Look at what it does. It keeps rural space in a world of urban sprawl. Food doesn’t come from a store, and wine doesn’t come from a bottle. It’s the benevolence of Mother Nature right here.”

That, and Upper Shirley’s creatives. When they decided to transform the place from a sleepy former appendage of Shirley Plantation to a working winery, Tayloe, recently appointed to the Virginia Wine Board by the governor, and Suzy, a laid-back equestrian, homemaker, and artist who raised two children here, knew it was all or nothing. So, they partnered with Charlottesville-based Michael Shaps, one of the state’s premier vintners, to make their wine, and Carlisle Bannister, an eminent local corporate chef and caterer, to command all things culinary. 

Shaps has already won for Upper Shirley two Governor’s Cup Gold Medals, the highest award for Virginia wine, for its Tannat and Zachariah blend. Bannister, a fourth-generation chef, has earned raves from critics and a loyal following for his innovative, fresh Southern cuisine. Both have attracted top talent to the Upper Shirley team, including Ernie LaBrecque, a banjo-playing former college wrestler who honed his cooking artistry at a Michelin-starred restaurant in Pittsburgh. “The absolute biggest surprise is the staff,” says Tayloe. “The staff wants to be part of something that sets high standards and performs at a high level. They set the agenda.” 

Pairings in the Pasture

That suits the Damerons, who are both hands-on managers and warm and willing hosts. On this night they marvel along with their guests—although a bit more knowingly—at the purple-and-crimson sunset reflecting on the river in front of the Presquile National Wildlife Refuge on Turkey Island from the spot that was once the Damerons’ pasture for polo ponies. “The view was too good for horses,” Tayloe quips. 

Working out of Katie, a 24-foot-long mobile kitchen truck (“K.T.,” get it?) parked on site for the occasion, LaBrecque unveils his first course—individual tarts. What appears to be a smooth crust, though, is really a ring of gnocchi made from squash. Inside, balls of roasted beets, pickled acorn squash, and goat cheese glisten like jewels in a pear and fennel gêlée, adorned with candied pumpkin seeds and fresh dill. And, yes, you could almost hear the jaws drop. It pairs well with Upper Shirley’s classic light, crisp 2015 Chardonnay, a specialty of Shaps, who trained in Burgundy and still makes his own wine there. 

Hickory-smoked duck breast and savory brioche bread pudding stuffed in crispy duck skin and glazed with AR’s Bourbon Barrel Aged Hot Southern Honey—unveiled on the occasion and whose creator, Ames Russell, is present—team up with Petit Verdot. Merlot-braised short ribs with bone marrow and German sweet potato gratin, pair with—you got it—Upper Shirley’s Merlot. 

The portions are all just right, leaving enough room for the finale, ginger ale pound cake with apple tart encased in caramel panna cotta and oatmeal crème Anglaise. Served with the Damerons’ Tobacco Barn Blanc, their private-stock Sauterne, this leaves a sweet but satisfyingly complex taste to linger on the palate as the conversation drifts off into the moonlit night. UpperShirley.com


This article originally appeared in our Drink 2018 issue.

June 11, 2022

Star Gazing and Laser Nights

Virginia Living Museum
July 9, 2022

Star Gazing and Laser Nights

Virginia Living Museum
August 13, 2022

Star Gazing and Laser Nights

Virginia Living Museum