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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


Alternate Route to Upper Shirley Vineyards

A section of Route 5 is currently under construction as a result of the heavy rainfall from this past week. We have detailed an alternate route for your convenience below. We hope to see you soon!

Directions with Current Detour

Follow signs for Interstate 64 E/Norfolk

Follow 1-64 E and US-60 E to VA-106 S/VA-609 S in New Kent County

Merge onto I-64 E

Take exit 200 for I-295 toward US-60/Rocky Mt NC

Keep right at the fork, follow signs for I-295 S

Keep left, follow signs for I-295 S

Keep left, follow signs for US-60 E

Take exit 22A for VA-5 E toward Charles City

Merge onto VA-5 E

Turn left onto Longbridge Road

Turn right onto Carters Mill Road

Turn right onto VA-156 S/Willis Church Road

Sharp left onto VA-5 E

Turn right onto State Rte 608

Slight left onto Westbury Farm Road

Turn right onto Shirley Plantation Road

Follow signs for Upper Shirley Vineyards

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The Babe is Now Open!

The Babe is now open every Saturday and Sunday, weather permitting, serving our outside food service and wine by the glass and bottle. This is perfect for anybody who wants to bring a blanket and sit out on the lawn to enjoy live music and Upper Shirley’s selections.

Michael Shaps & Tayloe Dameron, Eat it, Virginia!, Podcast:

In this episode of Eat It, Virginia!, Shaps shares the interesting story of how he got into the wine industry, what brought him to Virginia, and some of the secrets of his success. He’s joined by Tayloe Dameron, owner of Upper Shirley Vineyard and one of Michael’s wine partners.

“Michael Shaps is to Virginia wine what Michael Jordan was to basketball. In a word, dominant.”

Click below to listen to the podcast!



Latest Posts

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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