Beer, Wine & Spirits in Annapolis

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.

In addition to its elegant, warmly decorated lounge and hand-selected stock of wine, Crush Winehouse 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. Crush also makes all of its breads, dressings, desserts, and soups in-house everyday, and daily specials encourage patrons to try out new dishes.

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 or how to make educated wine purchases. For fans of the outdoors, Port of Leonardtown Winery partners with Patuxent Adventure Center for kayaking and wine adventures, where visitors enjoy a bottle of local wine after stalking it for miles between McIntosh Run to Breton Bay.

If comfort food is supposed to evoke a sense of ease and familiarity, the Impossible Double Hank burger breaks rather severely with tradition. With its intimidating name and heaps of lettuce, tomatoes, onions, bacon, and cheddar, the burger forces the brave patrons of Hank’s Tavern & Eats to confront their most delicious fears. Though less overwhelming than the double-portioned hamburgers, the tavern’s shrimp po’ boys, baby back ribs, and fish burritos are made with similarly fresh ingredients and prove just as tasty. While digging into these and other hearty eats, patrons can follow local sports on 20 TV screens and guesstimate their height by lying facedown on the 50-foot bar.

Founded in 1925, Morris Miller Wines & Liquor continues to embrace the marvels of fermentation and distillation by stocking its shelves with an international selection of potent spirits. The wine selection is grouped by region, allowing patrons to more easily track down a crisp New Zealand sauvignon blanc or a spicy Chilean carménère. On Friday and Saturday evenings, the staff hosts complimentary wine tastings, which allow customers to try small samples before they buy bottles to enjoy at home, in restaurants, or on the neighborhood's new roller coaster. Shelves of craft beer, single-malt scotch, and Brazilian cachaca round out the store's ample selection.