Jerry Bailey began homebrewing with friends in 1989, hopeful that the craft would bring fulfillment that his 9-to-5 failed to provide. Fulfillment it brought, along with numerous batches of tasty brew. Bailey couldn’t keep his inventions to himself; he quickly decided to open his own brewhouse as well as distribute his goods to other local establishments.
Today, Bailey proudly stands at the helm of both Old Dominion Brewhouse and Old Dominion Brewing Company. In the pub, chefs add variety to liquid meals with food such as burgers, crab cakes, and thin-crust pizzas while 30 flat-screen televisions keep patrons entertained with sports. The chefs also exhibit flair for Asian cuisine, slicing and rolling sushi and offering create-your-own mongolian stir-fries. At the bar, eight handles remain perpetually reserved for Old Dominion's craft beers, such as the award-winning Baltic porter and the Oak Barrel stout, which is loaded with flavors of vanilla and the color brown.
Port of Leonardtown Winery, a cooperative, crafts its red, white, and dessert wines with grapes sourced from southern Maryland vineyards. Along with private tastings, the winery hosts monthly events to draw in the community, including First Friday celebrations with tastings, local art, and live music held in the tasting room and on the patio. Classes help demystify the process of strolling down the wine aisle, discussing topics such as how to distinguish between various red-wine grapes and how to make educated wine purchases.
Since 1948, the Layton family has farmed a parcel of idyllic land that has managed to steadily grow in size over the years. As the farm changed hands through three generations, so did the agriculture?both literally, and figuratively. In 2007, Joe Layton and his clan re-evaluated the operation and decided to take a risk: they would plant wine grapes. Three years later, the winery opened its doors, and the fermented fruits of their labor were proof that the risk was worth it. Situated on 1,800 acres amid the lush rows of grapes, the winery is also home to a tasting room, and visitors are invited to explore the facility during daily tours or enjoy walking trails along the property.
St. Michaels Winery began its life in the Historic Old Mill complex, where it kicked off 2005 by introducing five new wines to the world. Shortly after, the awards began to roll in: golds, silvers, and bronzes from the Maryland Governors Cup and the Maryland Winemasters Choice Awards. Today, these industrious vintners offer sips and nibbles on a walk-in basis in their expansive, bright white and blue winery and tasting bar, amply stocked with 20 different varietals.
The Chesapeake Bay Maritime Museum is a non-profit organization dedicated to sharing the stories of the Chesapeake Bay and the people who have shaped their lives around it. With 18 waterfront acres in the historic town of St. Michaels, the Museum offers exhibits, boat rides, festivals and more.
Crush Kitchen & Winehouse
In addition to its elegant, warmly decorated lounge and hand-selected stock of wine, Crush Kitchen doubles as an intimate gathering place?a place that lets groups connect over small plates and test pairing tips doled out by knowledgeable servers. The wine list features premium, uncommon wines crafted by small producers from around the world, and wine-tasting events give patrons a chance to learn about pinot noir or American varietals from wine experts. Crush also makes all of its breads, dressings, desserts, and soups in-house everyday, and daily specials encourage patrons to try out new dishes.
Slate Wine Bar + Bistro
Slate Wine Bar + Bistro, carries on the family tradition of pouring fine wines in welcoming surroundings. A carefully curated selection of bottles?with an emphasis placed on wines?pairs with brunch, lunch, and dinner menus of New American cuisine. The wait staff offers insight so guests can perfectly match their meals of pan-seared duck breast with a red wine cherry sauce, grass-fed burgers, or seasonal risotto, and wine experts provide in-depth information in curated tasting events.