Road Trip: Maryland to Virginia

By: The Local Palate

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Create a choose-your-own wine adventure in Maryland and Virginia

Though they’re located in different states, neighboring counties Frederick, Maryland, and Loudoun County, Virginia, are united by their 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 counties’ proximity to Washington, DC, Baltimore, Maryland, and Alexandria, Virginia, makes them an ideal destination for a weekend jaunt or multiday getaway, but they’re worth making a trip to the Mid-Atlantic no matter where you call home. Depending on how much time you have, you can create your own road trip itinerary from our cheat sheet, which includes a mix-and-match list of vineyard tours and winery tastings, plus can’t-miss dinners, memorable overnight stays, and sought-after edible souvenirs.

Frederick County

SIP

Black Ankle Vineyards: 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: 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: 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 crafted 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.

Simple Theory Wine Co.: Pull up a bar seat or snag a leather chair in this downtown tasting room for a guided flight. Third-generation winemaker Melissa Aellen oversees the production at their 100-percent solar-powered winery in eastern Frederick County. Standouts include a crisp 2023 albariño redolent of tropical fruit and melon, and a rich, plummy 2022 petit verdot. Customize a Maryland-centric cheeseboard with artisan cheeses, pickled veggies, and local baguette prepared by Serendipity on Market downstairs.

EAT

Wye Oak Tavern: Martini service, flame-kissed steaks, and stellar seafood share top billing at chefs (and Frederick natives) Bryan and Michael Voltaggio’s steakhouse inside the Visitation Hotel. The fluke crudo with benne seed chili crunch is ace with a glass of rosé from Maryland’s Old Westminster Winery, while the smoked beet pastrami with Gruyère funnel cake makes for a whimsical shareable. The menu singles out the Queen cut black angus beef prime rib, but the rockfish in East Coast cioppino broth deserves its own callout. Finish with the gorgeous, deconstructed lemon meringue. For the best views of the dining room and the stunning altar-esque bar, ask to be seated on the mezzanine.

The Wine Kitchen: Sommelier 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 Loudoun County location in Leesburg, Virginia, that’s known for its six-course pasta tasting menu.

Gravel & Grind: This combination bike-and-coffee shop serves imaginative toasts like labneh with pistachios, candied orange, and honey alongside top-notch pour overs and specialty lattes. Try the CTC, a not-too-sweet medley of espresso, milk-infused horchata, cinnamon, and almond.

Juno Bakery: Stop by this Korean bakery early for first pick of Supreme Roll flavors like matcha or strawberry; snag custard- or red-bean-filled breads for a travel-ready snack; and peruse the warming case for savory delights like kimchi croquettes.

SHOP

Perfect Truffle: Locals flock to this third-generation chocolatier for truffles that look like a work of edible art. Classics like salted caramel and cherry cordial sit alongside unique offerings such as apricot Sichuan five-spice hazelnut.

Zoe’s Chocolate Co.: Pick up gift-worthy bars like dark Swiss chocolate swirled with Italian espresso or milk chocolate studded and topped with Route 11’s lightly salted chips. From the case, put together a box of chocolates including pistachio and black raspberry.

STAY

Visitation Hotel: If these walls could talk! This pet-friendly boutique hotel is housed in a building rich with 200 years of history, including turns as a cloistered monastery, Civil War hospital, and a private, all-girls Catholic school. The rooms are well-appointed like most contemporary luxury hotels, but the charm lies in the nods to the hotel’s storied past, including black-and-white historic photographs, preserved stained-glass windows, and original woodwork. Drop in for a drink or dinner at Wye Oak Tavern, located in the former chapel and home to striking Franz Mayer stained-glass windows, a marble altar base, and an Italian oil painting, The Presentation in the Temple. Snag daytime pastries or sandwiches from Acorn Provisions.

Loudoun County

SIP

EagleTree Farm Vineyards: Co-owners Lori McKeever and chef Jeff Judge bill EagleTree as a restaurant that makes wines to complement Judge’s homey-yet-haute menu. In the inviting dining room, try the wild mushroom arancini with the 2021 Talon, a medium-bodied red blend that cuts the richness, and the filet mignon with potato-garlic puree with a velvety 2017 Tannat. Come summer, pair sips with alfresco wood-fired pizzas, like the signature white pear and caramelized onion.

Fabbioli Cellars: Co-owner Doug Fabbioli rightfully embraces his nickname as The Godfather of Loudoun wine at Fabbioli Cellars, where he produces fan favorites like Tre Sorelle, an earthy Bordeaux-style estate blend of merlot, petit verdot, cabernet franc and cabernet sauvignon reserve, and a 2017 tannat varietal redolent of bright wood and cherries. A standard tasting includes six wines paired with gourmet bites from senior manager Anne Tucker’s clever monthly-themed menus, ranging from Taylor Swift to Harry Potter.

Stone Tower Winery: The Huber family’s Hogback Mountain winery sits on more than 400 acres of rolling hillsides and boasts two tasting rooms, the family- and pet-friendly Harvest Barn and the members-only Tower View. Opt for a tasting flight or pair a glass of bubbly, like the beguiling 2020 Estate Blanc de Blancs, with truffle fries. Book tours like a behind-the-scenes Cellar Tour or the Estate Experience, which includes a golf cart tour and a three-course lunch paired with premium estate bottlings.

Bluemont Vineyard: This multigeneration winery, owned and operated by the Zurschmeide family, sits on the east-facing slopes of the Blue Ridge Mountains. For the best views, snag a seat outside and opt for either the farm series or signature wine tasting, the latter of which highlights award-winning winemaker Scott Spelbring’s most notable sips, like a crisp and refreshing albariño and a rich, black currant-forward cabernet franc reserve. On weekends, order the brunch board and a bottle of sparkling Daydream rosé.

Williams Gap Vineyard: When you step into this elegant Bluemont tasting room you’ll be greeted by an impressive lineup of medal-draped bottles. Many are part of the wine tasting, including petit verdot, a bold red redolent of black tea and cherry, and Williams Gap Red, a plummy number with violet aromas.

EAT

Tuscarora Mill: Tuskie’s, as it’s called by locals, is a Leesburg staple for farm-fresh fare and superb seafood. Signatures include fried green tomatoes and crab cakes, but be sure to entertain specials like crab-topped rockfish and the popular seafood salad with shrimp, lump crab, and seared peppered tuna over greens dressed in an irresistible Madras curry oil. Save room for dessert, like the peanut butter chocolate mousse cake paired with Fabbioli Cellars’ Raspberry Merlot.

Knead Wine: Master sommelier and Culinary Institute of America-trained chef Jarad Slipp marries his talents at this inviting wine shop and pizza joint (with locations in Middleburg and Purcellville). Many of the Neapolitan-esque pies are named after rock legends, like the EvH (Eddie Van Halen), a souped-up pepperoni pizza anointed with chile-spiked honey and pickled jalapeños. Wines are sourced from all over the world and smartly organized by price point ($25 or $40), including top Virginia producers like Linden Vineyards and Loudoun County’s Walsh Family Wine.

SHOP

ROOTS 657 Café & Local Market: Chef Rich Rosendale’s market features a curation of local artisan products that make great edible souvenirs or gifts. Think infused honey, barbecue sauces, maple syrup, baking mixes, spice rubs, and hot sauces. If you arrive hungry, hit up the café for the signature smoked brisket sandwich piled onto a toasted jalapeño-cheddar roll with marinated slaw, or the tomato-and-corn soup topped with a small scoop of briny-sweet Maryland crab.

STAY

Stone Gables Bed & Breakfast: Housed in a renovated barn on a former orchard site just outside downtown Leesburg, this cozy B&B feels like a home away from home thanks to owners Travis and Frances Prott’s warm hospitality and thoughtful amenities like a morning coffee bar and anytime tea and microwave popcorn. Travis pulls double duty as the Tuscarora Mill’s wine director; order some of his sommelier picks to sip in one of the B&B’s cozy nooks or while you take a soak (request the spacious Stone Gables Suite for a clawfoot bathtub). He also helms breakfast when he turns out fruit parfaits, omelets, and pancakes.