Frederick County, Maryland, is known for its bucolic rolling farmlands, charming downtowns brimming with restaurants and shops, and a plethora of wineries turning out top-notch wines, from robust reds to complex whites to supple meads. The county’s proximity to Washington, DC; Baltimore, Maryland; and Alexandria, Virginia, makes it an ideal destination for a weekend jaunt or multiday getaway, but it’s worth making a trip no matter where you call home. These are our five picks for some of the best places to experience Maryland’s wine culture.
Simple Theory Wine Co.
Frederick
Reserve a Theory Tasting at this wine shop for a guided introduction to the Simple Theory portfolio of wines made from European varietals. Third-generation winemaker Melissa Aellen oversees the production at their 100-percent solar-powered winery in eastern Frederick County. Or set up a table reservation for a two-hour pick-your-own wine and snack pairing. Standouts include a crisp 2023 albariño redolent of tropical fruit and melon, and a rich, plummy 2022 petit verdot.

Black Ankle Vineyards
Mt. Airy
Stepping into this tasting room feels like being transported to a Tuscan villa, complete with reclaimed building materials from the farm including wood, stone, straw, and clay. Owners and winemakers Ed Boyce and Sarah O’Herron have earned a following for their cellar-worthy Bordeaux blends, like Crumbling Rock, an elegant, smooth blend of cabernet franc, cabernet sauvignon, malbec, merlot, and petit verdot, and Passeggiata, a fan-favorite red redolent of dark cherry.

Catoctin Breeze Vineyard
Thurmont
Nestled in the northeastern foothills of the Blue Ridge Mountains, this family-owned vineyard grows grapes that benefit from the ancient, slate-rich Appalachian soil and cool breezes from Catoctin Mountain. Whether you opt to sit on the shaded patio or in the quaint, airy tasting room, seek out their flagship wine, Concerto, an elegant Bordeaux blend that winemaker Adam Fizyta describes as having a floral bouquet and ripe flavors of black cherry and blackberry.
Loew Vineyards
Mt. Airy
Established in 1982, this is one of Frederick County’s oldest wineries. Fifth-generation winemaker Rachel Lipman produces award-winning varietals like cabernet franc and malbec and honors her family’s centuries-long mead-making legacy by crafting complex honey wines utilizing her grandfather’s proprietary equipment. Try the sought-after Malka, a barrel-aged, Polish-style mead made with local wildflower and clover honey that’s named after Malka Löw, owner of the family’s first meadery and the grandmother of cofounder William Loew.
The Wine Kitchen
Frederick
Wine director Sam Scarlett’s approachable wine list is organized by witty categories like Paint the Town Red, billed as bold reds fit for a party, or I’m Not Drinking Any F#$%ing Merlot, a cheeky Sideways reference. Pair a glass with inventive dishes like dill pickle hummus with hot sauce falafel or mussels in a heady coconut curry broth with dunkable toasted focaccia. The Wine Kitchen also has a location in nearby Leesburg, Virginia, that’s known for its six-course pasta tasting menu.
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