Maryland’s Eastern Shore Wine Guide

Guest post by Bob & Ronna Chew

5 Great Small Vineyards in Maryland’s Eastern Shore Region

There are 12 amazing wineries on the Chesapeake Wine Trail, and a few are genuinely remarkable. Due to the coast’s fertile soil, many types of grapes are grown here, meaning various kinds of wines can be produced in the region. Those seeking to spend an afternoon visiting the best small vineyards on Maryland’s eastern shore will find these five locations to be both visually stunning and palette pleasing.

Casa Carmen Wines

In small, historic Chestertown is the boutique family-run vineyard Casa Carmen Wines, where the purveyors produce dozens of small-batch wines and vermouth. Most of the vineyard’s wine collection leans toward the dryer side, but they are flavorful, well balanced, and easily stack up to national and international selections. Make a reservation for intimate tastings in the wine room, and purchase bottles of your favorites to take home.

Crow Vineyard & Winery

Crow Vineyard & Winery is an authentic working farm and a highly regarded Maryland coast vineyard and production facility. Guests can take their glass of wine, tour the farm’s trails, and learn more about the winemaking process. Open year-round, this award-winning winery is also a lovely venue that hosts monthly events.

Many plan their visits here around live music nights, dinner theaters, wine pairing classes, and special multi-course tastings. Grilled feast events feature the farm’s grass-fed beef to complement red wine flights. The location is open daily and can be booked for private tastings, special events, and group tours.

Mark Cascia Vineyards & Winery

Planning a vacation in the Annapolis area and want to add a visit to a Maryland eastern shore winery to your itinerary? Situated right on the waterfront of the Chesapeake Bay, Mark Cascia Vineyards & Winery is a top-notch family-owned wine purveyor in nearby Stevensville. The vineyard has 12 acres of premium grapes that are used to create an array of red, white, dessert, and more wine varietals.

Each hand-crafted wine is an experience for the palette, and many of their labels have earned high awards from wine enthusiast publications regionally and nationally. Mark Cascia Vineyards & Winery also makes a sensational backdrop for special occasions, weddings, and other events. They have a sizable event space and can offer guests catering and table service.

Triple Creek Winery

Four brothers dreamed of starting a winery, so they transformed a portion of their working farm into the family-operated Triple Creek Winery along Maryland’s eastern coast. As an agriculturally inclined family, even the youngest members pitch in picking grapes and pruning vines, making their production and growing processes unique.

While the vineyard is not large, the variety of nectars crafted and served to visitors here is huge in flavor. The winery offers small, laid-back tasting excursions in their renovated barn. The space invokes a sense of nature, with high wooden beams, a custom bar, and communal tables where patrons can interact and visit over flight samples, glasses, and bottles of red and white wines.

The converted barn is available for private events, such as wedding receptions, family reunions, and other types of retreats. Stop by to see what’s on the wine list, or tour the on-site shop to pick up a few unique labels to take home and enjoy later.

St. Michaels Winery

Visitors to St. Michaels Winery can treat themselves to daily tastings and tours. The winery always has at least 18 hand-crafted wines, including whites, reds, varietals, and sweet dessert wines, for patrons to partake in amid a cozy tasting room in the Historic Old Mill District. Many of their labels have won multiple awards, both internationally and regionally.

St. Michaels Winery is located on the waterfront and offers exceptional views of the eastern shore of Maryland. The property’s beauty makes it an ideal place for weddings, receptions, and other social gatherings. Come by to tour the vineyard and production area, or check out the tasting room to inquire about booking it for an upcoming event.

Experience These Small Vineyards in Maryland’s Eastern Shore

Take a day to explore some of these top boutique wineries located on Maryland’s coastline for a unique and fun experience. While most have dedicated areas, many of these locations will open their doors by appointment for private tours, corporate gatherings, and special events. Whether a tour, tasting, or just picking up a nice bottle of wine to take home is on the agenda, these small vineyards won’t disappoint.