The Virginia Peninsula Wine Trail

Upper Shirley Vineyards

Owner Suzy Dameron founded Upper Shirley Vineyards, which currently has 22 acres planted with grapevines, in 2016, a mile off the Capital Trail. 

With the James River in the background and the Presquile National Wildlife Refuge across the river, Upper Shirley’s views add to the pleasure of sipping their award-winning wines. Crafted by winemaker Michael Shaps and wine director Tayloe Dameron, they won three golds and four silvers at the 2024 Virginia Governor’s Cup, including a gold for the 2018 Zachariah, named for Dameron’s grandfather.

Guests can unwind in their tasting room, on the expansive porches, or bring blankets and lawn chairs to create their own sipping spot. The restaurant offers shareables and main dishes. Dogs, outside food and beverages are not permitted. Open Thursdays through Sundays.

EVENTS:

• June 7: Sixth annual Rockin' Under the Stars with Full Moon Fever
• June 28: All Out 80s Concert with The Deloreans

Jolene Family Winery

Located on property that’s been in the family since the late 1960s, Jolene Family Winery was originally a garden center and plant nursery. Siblings Sandy Lewis andBrian Mikelaites, the winemaker, opened it as a winery in 2020, named in honor of their parents, Joseph and Helene. 

Their Family Red and Family White blends are the vineyard’s anchors, but Jolene offers wine for every taste. Their most recent awards include the 2024 Virginia Wine Invitational by Libation where they won Gold for four of their wines and double Gold for their Cabernet Sauvignon. 

Visitors can enjoy views of 18-acre Tom Brooks Lake where waterfront tents can be rented hourly, and a multi-level patio invites lingering. The original greenhouse extends the tasting room with a fireplace and often hosts live music, while the pavilion provides another option. Open Thursdays through Mondays.

EVENTS:

• March 15: Cheesecake Pairing
• April 6: Spring Vendor Market

New Kent Winery

Joe and Jo Anna Dombroski purchased the winery in 2014 and went on to plant 10 additional acres of vines and build another wedding venue. In 2020, they expanded to open the county’s first farm brewery, Talleysville Brewing Company.

An oversize chessboard greets visitors in the front yard. Two porches and a courtyard with tables and chairs welcome guests. Inside, the feel is cozy, with heart pine floors logged in New Kent County and doors from Richmond’s Jefferson Hotel. The menu ranges from appetizers such as spanakopita, crab cakes and samosas to basics such as charcuterie, soft pretzels and pimento cheese.

Winemaker Tom Payette won gold medals at the 2024 Virginia Governor’s Cup for their Reserve Chardonnay and Merlot. Open daily.

Saudé Creek Vineyards

Winemaker/owner Jason Knight opened Saudé Creek Vineyards in 2011, making it a destination for relaxation, with live music every Friday night, Saturday and Sunday year-round, with a food truck on-site.

The tasting room has the feel of a lodge with a massive stone fireplace where you’ll often find the winery cat, “Mr. Saudé,” who appeared during construction and never left. A large wraparound porch and upstairs loft provide plenty of space for sipping and admiring the views. 

They’ve won multiple silver and bronze medals in the Virginia Governor’s Cup. Saudé Creek Red, their most popular wine, is an easy drinking table wine that pairs with anything from barbecue to chicken to pizza. Vidal Blanc, known as “champagne without the bubbles,” is another favorite. Open Wednesdays through Mondays.

EVENTS:

• March 15: St. Patrick's Day Celebration with live Irish music, food truck, shamrock sangria
• April 26: Spring Sip & Shop – 20+ local vendors, food trucks, live music
• May 11: Mother's Day – food trucks, wine slushies
• May 26: Memorial Day with food truck, live music, wine slushies
• June 21: Backyard Beach Party with buffet-style live music, food trucks

Gauthier Vineyard

Founded in 2014 by Navy veterans Sandi and Mo Gauthier, Gauthier Vineyards is a woman- and veteran-owned working farm, equestrian center, vineyard and winery. 

Winemaker Matthew Meyer has years of experience in Napa Valley and Virginia. Gauthier grows Norton, Virginia’s indigenous grape, on-site and all other grapes come from their satellite vineyard at Mt. Jackson in the Shenandoah Valley.

With a wide, wraparound porch surrounding the tasting room, Gauthier also offers a patio and firepit overlooking a pond. Heaters and blankets are available when the weather’s cool. The tasting room offers wine tastings and flights, a wood-burning pizza oven and a tranquil atmosphere for those 21 and up, with younger visitors and dogs welcome outside or on the porch. Annual events include a Mardi Gras celebration, Spanish pig roast, paella parties and Wines of the World tastings with the winemaker.

Williamsburg Winery

Virginia was the first colony to actively sustain vineyards for wine. Williamsburg Winery planted its first grapes in 1985 on a 400-acre property dubbed Wessex Hundred, releasing their first wine in 1988 and earning their first Virginia Governor’s Cup in 1990. Today, with 59 acres under vine, the winemaker is Stacey Lightfoot, one of only 10 female head winemakers in Virginia.

In the tasting room, two suits of armor stand guard over a light-filled space that seats 80 with a fireplace and tasting bar. Tours of the winery, vineyard and cellars are available by reservation. 

Across the road, the Gabriel Archer Tavern, named for the property’s original owner, offers lunch, dinner and brunch, while the adjacent Pavilion offers warm weather dining and live music.