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A Dazzling Riverside Estate

Thirty minutes from Richmond

Come experience the magic of Upper Shirley Vineyards, a one-of-a-kind estate, winery, restaurant and wedding venue perched above one of the most scenic bends on the James River. Here in Tidewater Virginia the hours unspool at a more gracious pace. Senses awaken, and stress melts away, leaving you space for more meaningful connections with friends and family.


30 minutes from downtown Richmond, and 35 minutes from Williamsburg, located just off Route 5 and the Capital Bike Trail, Upper Shirley Vineyards is ensconced in a rural wonderland. The estate boasts history and scenic beauty on an epic scale and an embarrassment of culinary riches—bottomland produce, fresh-caught seafood—and world-class wines made from our own estate-grown grapes. 

Each bend in Route 5 takes you deeper into American history.
— National Geographic


Rockin' Under the Stars

Join us for a night under the stars featuring Full Moon Fever: A Tom Petty Tribute Band.  Come out for an evening of music, Upper Shirley cuisine, Upper Shirley wine, iced cold beer & fun.

 Click here for more information and to purchase tickets.

Owner Tayloe Dameron featured in Ledbury

Thank you to Ledbury for including our owner, Tayloe Dameron in their Sunday Shirt Program. Click here to read the interview! 

USV Wedding Features

We are so excited to share that two of our beautiful weddings have been featured! 

Check out the full articles, Classic Blue + White Southern Wedding by Elizabeth Ann Designs and Meghan & Jim's Upper Shirley Vineyards Wedding by Blushing Richmond. 

Join Our Official Wine Club, The Zachariah Society

The wait is finally over... We are thrilled to announce the launch of The Zachariah Society! An exclusive one year wine club membership, ideal for the Virginia wine enthusiast. 

For further details and to join the society, click here

Richmond Times-Dispatch Restaurant review: Upper Shirley Vineyards pairs a beautiful location with stellar food

Jo Lord, food critic for the Richmond Times-Dispatch, concluded her review of Upper Shirley Vineyards with the following: "... the dining experience at Upper Shirley Vineyards is something special, indeed. I plan to visit again soon and suggest you do the same." Read the full article to see why she and others are calling Upper Shirley a must visit vineyard!

2014 Zachariah Wins GOLD in Governor's Cup!

Out of 494 entries, only 23 gold metals were awarded this year. And our Zachariah was one of them! Full article here.



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Hour-long ride that meanders through Upper Shirley's vineyard and surrounding trails as your guide walks you through the vineyard history, the process of grape-growing, and the roll Charles City and Upper Shirley had to play in America's past. Hosted by Two River Trails.

4 to 5-hour, 10 mile leisurely bike ride devoted to the amazing history and health of the Charles City County area and her beautiful James River that has rightly been called The River Where America Began. Rides begin and end at Upper Shirley. $125-$165 (lunch at Upper Shirley optional), wine tasting included.


They say wine is made in the vineyard


Ours begin as grapes grown both in the piedmont and here on the estate. The fruit at Upper Shirley Vineyards is bathed by river breezes and nourished in the Tidewater region’s deep Pamunkey soil, the oldest tilled earth in the United States. We tend our vines by hand, using age-old methods. It’s demanding work but worth the effort. One taste, and you’ll understand why.


Featured in

Upper Shirley Vineyards specializes in award-winning wines... stunning views, dream weddings [and] cuisine that’s beautifully prepared and equal to the allure of the place in every way.
— Jo Lord, richmond times-dispatch
Easily the region’s most spectacular wine venue…a showpiece that will draw visitors from all over the Commonwealth.
— The Virginia Grape
The aesthetic is clean, streamlined and contemporary.
— style weekly
The cuisine was superb... The ambiance of the winery was lovely, everything seemed to sparkle.
— The Progress-Index
Upper Shirley Vineyards isn’t becoming a destination point. It has become a
destination. . . . The view is spectacular. Ditto the wine. Double ditto the food.
— Jack Berninger, Richmond Times-Dispatch
The South’s most seductive burger and view combo
— Garden & Gun
There is nothing prettier than a ride up Route 5... The Vineyard’s rows of grapevines are picturesquely set right on the James River.
— The Southern Coterie's Mini-guide to Williamsburg
The chardonnay and viognier are exceptional. Perhaps even better are the sparkling wines, rosé, and red tannat.
— Jim Raper, Distinction Magazine
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