New Leesburg October One Tasting Shop Showcases Virginia Wine

By Dana Armstrong

A quick glimpse at the signs around October One’s new tasting shop in downtown Leesburg reveals owners Bob and Loree Rupy’s philosophy on vino. A neon sign in the back glows “Virginia Wine” in electric purple. A framed quote attributed to Loree reads, “It’s a good wine if you like it.”

“We like to keep it simple, and we love to tell the stories behind the wines. With having all of these Virginia wines and other Loudoun County wines here, we try to get the backstory,” Bob Rupy said.

The Rupys are the husband-and-wife team in charge of October One Vineyard and, now, October One Tasting Shop. They opened the doors to their tasting shop on Loudoun Street on July 13 and celebrated their grand opening on Aug. 27.

The Rupys began their wine journey in 2006 when they worked at Bluemont Vineyard with some friends. Loree worked in the tasting room. And Bob, though he didn’t have a wine background or chemistry degree, became a student of the wine-making process.

In 2015, the Rupys separated from Bluemont Vineyard to dive further into the wine industry on their own. There was a shortage of wine grapes in the region at the time. They hoped to find a location to grow grapes and supply the fruit to Bluemont Vineyard and other Loudoun County wineries.

They found a 30-acre plot near Bluemont with just the right elevation and soil to cultivate their grapes. They named their property October One Vineyard, an homage to their wedding anniversary.

With the help of their friend and Vineyard Consultant Doug Fabbioli, and their Vineyard Manager Severino Maya Garcia and his crew, the Rupys transformed their Viognier, Albariño, Merlot, Cabernet Sauvignon, and Cabernet Franc varietal grapes into incredible, award-winning wines.

As Loree said, “Well, if we’re going to produce some grapes, we might as well put the name on it and sell it.’ And then the thought was ‘where would we sell it?’ since we didn’t have a tasting room.”

By 2018, they had 400 cases of their 2015 vintage ready to sell. Their answer was in the local farmers markets around Leesburg and the Cascades.

“It’s a farm product. We thought that was a good place to connect with the local community that was interested in local things and interested in local wine. And it was a great place to build our brand, sell wine, and sell our wine club,” Bob said.

Their wine soon gained popularity with customers—especially their Albariño white wine. The Albariño grape varietal is native to Spain and Portugal and is a relatively rare find in Virginia. Although the grape grows well here, the vines produce half as much fruit as other varietals. Therefore, not many growers choose to plant it.

But the Rupys say the growers who do choose Albariño reap the rewards. Its light-bodied, citrus flavors and high acidity make for a refreshing pour. The Albariño is their fastest-selling wine and won Best of Class in the 2020 Loudoun Wine Awards.

The new October One Tasting Shop in downtown Leesburg gives longtime winemakers Bob and Loree Rupy a place to showcase their wine from Virginia-grown grapes. [Renss Greene/Loudoun Now]

That’s not October One Vineyard’s only claim to fame. In the 2021 Virginia Governor’s Cup, their 2019 Cabernet Franc won gold, and their 2019 Merlot and 2019 Cabernet Sauvignon won silvers. Their 2020 Viognier also won the Chairman’s Grand Award in the 2021 Loudoun Wine Awards.

“As we grew, there were some cumbersome aspects to the logistics and being at the farmers market with all this wine,” said Bob.

“You can only do so much when you’re traveling with a large amount of product—especially a volatile product that does not really care for the changes in weather,” Loree said.

It was time for the Rupys to find a more sustainable, year-round location. Luckily, they found the ideal space for a tasting shop within walking distance of their longtime home in Leesburg.

October One Tasting Shop offers all the wine varietals from their vineyard and a monthly, rotating menu of wines from all over the state. They seek to learn the backstories behind every wine and brand they sell to convey the same in-depth information about other vineyards’ wines as they do with their own.

“There are great conversations to have about wine growing in Virginia. And I like to embrace our varied growing conditions from year to year. We’re really leaning into it as far as our brand goes and trying to show people Mother Nature’s hand in the process in Virginia,” Bob said.

He hopes to curate wine lineups that show the effects of different soils, weather conditions, and producers’ hands on the wine’s properties: its color, acidity, alcohol content, and flavors.

“We have a lot of pride in our local industry in Virginia, so the more people we can tell about it, the more excited we get about it,” he said. “I love meeting people from different places and turning them on to local products. That neon sign, Virginia Wine, let’s tell more people about it and have them taste it.”

October One Tasting Shop is open Wednesday through Saturday from noon to 7 p.m. and Sunday from noon to 6 p.m. It’s located at 7 Loudoun St., SW, Leesburg, VA 20175. For more information, go to

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