The Chesapeake Bay Wine Trail

Monroe Bay Winery & Wedding Venue

Kiki Apple and Walter Lamore of Monroe Bay Winery produced their first bottles of wine in 2014 at their waterfront property on part of the James Monroe birthplace farmland. Their 3,000-square-foot air-conditioned Strawbale Barn, notable for the recycled wine bottles built into the walls, opened in 2019.

In addition to wine, Monroe Bay also produces several different ciders. Guests are always welcome to bring picnics. With plenty of shaded outdoor areas, four-legged friends are welcome and the creek front makes an ideal place to enjoy a bottle of wine or cider. Monthly comedy nights are popular. Open Saturdays and Sundays, April through December only.

Ingleside Vineyards

Founded in 1980 by Carl Flemer Jr. and his son Douglas on land their family has owned since 1890, Ingleside Vineyards is one of Virginia’s oldest wineries. Today, winemaker Zach Pierce produces more than a dozen wines, including Petit Verdot and Albariño. Ingleside is a three-time winner of the Virginia Governor’s Cup.

Their tasting room, open year-round, includes a cozy sitting room as well as the barrel room. The outdoor courtyard has a European feel, with trees growing between tables, a fountain and lights strung overhead. Three adjacent porches provide additional seating and dogs are welcome. Open daily.

EVENTS:

• March 23: Souper Sunday offers a bowl of hot soup and a glass of wine
• Memorial Day weekend through Labor Day: Summer Music Series

General's Ridge Vineyard

Rick and Linda Phillips planted their first grapes at General’s Ridge Vineyard in 1999 and today grow 35 acres raising 15 grape varietals. Winemaker Michael Shaps produces 17 different wines, including bestsellers GRV Red and GRV White, both easy-drinking table wines. 

The original tasting room opened in 2010 with an intimate feel and has since been complemented by the Vines Room, a larger, elevated space with extensive views, a patio and a deck. Board games, live music and a kitchen providing a full menu are available. Music, a major draw, happens Fridays, Saturdays and some Sundays. Open Fridays through Sundays.

Rivah Vineyards at the Grove

Rivah Vineyards at the Grove was begun by Bryce Taylor in 2013 to reimagine how his family’s farmland was utilized. Taylor died in 2023 in a car accident and his father, Bill Taylor, continued the winery in his son’s memory.

In addition to the tasting room with a rollup door that provides views of the property, there’s a separate event space. A pier is provided for guests who arrive by boat, while those who don’t, may want to stroll down to the water. A patio with heaters and a nearby firepit add outside warmth on cooler days. 

Rivah Vineyards’ Cool Breeze and Yeocomico White are perennial favorites and pair especially well with seafood. Guests are welcome to bring their own food. Open Saturdays and Sundays.

Jacey Vineyards

Ophthalmologist Robert Jacey first planted grapes at Jacey Vineyards in 2005, and as winemaker created his first vintage in 2010. Fifteen years later, the 2021 Albariño and 2019 Malbec are bestsellers.

Two yellow labs are the official greeters at this family-owned, dog-friendly vineyard where guests are welcome to play the grand piano, guitars, drums and other instruments in the tasting room. Visitors can arrive by land and water, the latter via piers on Mill Creek. Pro tip for boaters: call ahead and the winery will send a Gator to ferry guests.

A full kitchen offers charcuterie, made-to-order pizzas and oysters. Beginning in early April, brunch will be served on Sundays. Open Fridays through Sundays.

EVENT:

• April 26-27: Spring Oyster Crawl

Ditchley Cider Works

Located on 162 acres, Ditchley Ciderworks was opened in 2018 by Navy veterans Cathy Calhoun and Paul Grosklags. With a 10-acre apple orchard planted with 50 apple varieties, a herd of grass-fed cattle, free-range heritage breed pigs, ducks, geese and turkeys, Ditchley is very much a working farm, as reflected in their farm-to-table seasonal menu. Sunday brunch with cider Mimosas is popular, so reservations are recommended. 

In addition to the indoor tasting room, the outdoor tasting room provides a scenic place to relax and sip cider under umbrellas and a large canopy. Dogs are welcome, outside food is not. With Calhoun as cidermaker, the ciders range from simple to full-bodied, with varieties to appeal to wine or beer drinkers; Ditchley Blush and G8 are crowd favorites. Accessible by water, the sandy beach along Dividing Creek makes a worthwhile post-sipping destination. Open Saturdays and Sundays.

Good Luck Cellars

Paul and Katie Krop opened Good Luck Cellars in 2011. After Paul passed away unexpectedly in 2020, Katie continued the farm winery with Denny Sulick, originally Paul’s assistant, as winemaker. Chardonel, their flagship wine, is a prolific white wine grape they’ve grown and bottled from the beginning, with each vintage produced having won an award. They’ve won 85 medals since 2011 from multiple wine competitions, including the Virginia Governor’s Cup.

Good Luck offers 4,500 square feet of indoor space between its cozy tasting room and adjacent event space under a cupola with a sweeping view of the estate. Enjoy the covered porch, and don’t miss the nine rescue hounds who make up the Vine Patrol Squad. Food truck and line dancing every Friday evening. Open Thursdays through Mondays.

EVENTS:

• March 30: Chamber music concert with food truck
• April 26-27: Oyster Crawl weekend with oyster and food vendors, live music, local artisans and TOGA on-site

The Dog and Oyster Micro-Vineyard and Oyster Bar

The Dog and Oyster Micro-Vineyard and Oyster Bar is in the heart of downtown Irvington under a clear tent in front of the Hope & Glory Inn and edged by Petit Manseng grapevines. In the wine and oyster pairing business for 15 years, the name honors the rescue dogs it owned in the past to protect grapes from deer, while also honoring one of the Chesapeake Bay region’s greatest assets, the oyster.  

Four of the Dog and Oyster wines are offered by the flight, glass, bottle or case. Over the years, they’ve won scores of medals, including from the Virginia Governor’s Cup and San Francisco International. A full bar is also available.

The menu offers an array of locally sourced raw and roasted oysters, house-made charcuterie, gourmet hot dogs, pomme frites, Bloody Marys and Bloody Mary oyster shooters. Open Fridays through Sundays.