After a decade of pouring pinot, Diane Gross decided that there was only one place to go: up. Cork Wine Bar has moved north, settling down above sister business Cork Market & Tasting Room.

Gross, the owner (along with husband Khalid Pitts), waxed poetic about the past ten years, having seen her nook of 14th Street grow from a mostly-locals territory to a bustling, popular block of bars and restaurants.

Husband-wife co-owners Diane Gross and Khalid Pitts

“When we opened Cork, we wanted to create a local gathering spot offering great wine, food and service… Now we have the flexibility to be more innovative and fun.”

Gross credits her Jewish upbringing with the inspiration to create this community environment. Her childhood memories recall warm, welcoming dinners. There was always room for more at the table, a philosophy that she brings with her today (and one that her servers aren’t always thrilled about).

Having this strong Jewish background “fundamentally informs what I care about,” she said.

Ironically, wine didn’t play a large role at the table growing up. But after moving to DC from LA, she became interested in wine. Gross went on to earn her law degree in New York, frequenting cozy corner wine bars for brief respites from writing briefs.

Moving back to DC, she settled into the 14th Street Corridor and met her now-husband and business partner. She began a job in the Senate in 2004, but being in the political minority, she soon felt the tug of starting fresh and letting her dream of opening her own neighborhood wine shop come to fruition. Over the course of one just year, Gross opened a restaurant and got married. In 2008, Cork was born—right around the corner from her home.

Accolades swept in, including Washingtonian’s “Restaurateurs of the Year” award in 2009. Ever since its opening, Cork has maintained its philosophy of offering chef-driven, seasonally inspired small plates paired with Old World wines without pretension.

“We aren’t serving trophy bottles. We are serving options you can have on a Tuesday,” she said. Though the wine list is long, it’s approachable, even with unfamiliar grapes and unexplored subregions.

Old World wines, she said, spoke to her. Gross sources only small-production estate wines, while endeavouring to remain affordable.

When Cork opened, diners wondered where they could purchase the wines served at dinner. Ever the entrepreneur, Gross opened a nearby bottle shop: Cork Market.

A decade later, the wine winds have shifted. A new DC license allows establishments to serve wine for both on- and off-premise consumption. Now, customers can take classes, have dinner and grab a bottle to go, all in the same space.

While the restaurant has stayed thematically similar while moving physical spaces, the market downstairs has gone the other direction. A bar greets customers right at the door, across from artfully displayed bottles. Farther back is a cafe featuring snacks and charcuterie plates. The market, downsized, sells sundries—and a cheesemonger is on staff to ensure the best Roquefort for your red.

At the end of a long week, chatting over a golden-hued Royal Tokaji Aszú dessert wine from Hungary, Gross mused about the “innovative and fun” aspect of the reimagined business.

“Since we have this license, we’re going to start to make wine ourselves,” she said, “Rosé.” They will source juice from a single Shenandoah vineyard, and then process onsite. The rosé will be served in-house only, for now. They’ll have a winemaker consultant from the vineyard should anything go sour. This relationship speaks to their ethos of the importance of cultivating relationships behind the wine.

Now that the dust has settled, Gross admits that her most pressing concern falls to a difficult pairing. Avocado toast, inspired by Gross’ California past, arrived on the menu in 2008 before it became a millennial meme. Yet avocado is notoriously difficult to pair with wines. Her solution is the Domaine Larredya from Jurançon. It has citrus that “finishes with beautiful acidity, which compliments and contrasts the creamy mouthfeel of the nut, avocado and oil.” It’s strong yet not overpowering, approachable and warm and bright. Just like Cork.

Cork Wine Bar & Market, 202-265-2675, 1805 14th, NW, Washington, DC, Tuesday–Wednesday 11 am–midnight, Thursday–Saturday 11 am–1 am, Sunday 11 am–10 pm. Not kosher.