Maryland Wine Country Tours from DC

This is a private chauffeured wine tour to Maryland’s wine country, the quieter alternative to the Virginia tours most DC visitors know. You ride in an executive sedan, a black executive SUV, or a Mercedes Sprinter, your chauffeur drives the whole day, and you visit three wineries across the Montgomery and Frederick County region north of DC. Plan on 6 hours door to door (the minimum for any wine tour). The drive from DC up I-270 and I-70 to the Mt. Airy and Westminster area runs about 45 to 60 minutes each way, so the wineries sit close enough for an easy day and far enough to feel like a real trip out of the city.

Maryland has more than 80 wineries, and the ones near DC have a different character from Loudoun County. Many are smaller, estate-grown, and willing to experiment. Black Ankle Vineyards, for one, dry-farms its vines (no irrigation) and makes a small-yield Cabernet Franc you will not find at the larger Virginia producers. That kind of specific, local wine is the reason to point the car north instead of west.

How the day works

We pick three wineries within about an hour of DC and give you a relaxed pace among them, roughly two hours per stop including the drive between. Your chauffeur arrives at your DC, Maryland, or Northern Virginia address at the time you set, loads the group, and handles every mile of driving, parking, and the route between vineyards. The Sprinter is the better choice for groups: it seats up to 13, has room to spread out, and keeps a bachelorette party or a corporate group together in one vehicle instead of caravanning.

You do not plan the route or read a map. This is a private, chauffeur-guided tour: we pick the three wineries below, so tell us a rough start time and your taste profile when you book, and the wineries, drive order, and lunch timing are arranged for you. Want a different winery or stop swapped in? Just ask, and we tailor the DC wine route to you.

Maryland wineries we build the day around

Tell us your taste (dry reds, crisp whites, sparkling, natural wine, food pairings) when you book and we select the three that fit best. These are the producers we return to most.

Boordy Vineyards in Hydes (Baltimore County) is Maryland’s oldest winery, a 200-acre farm with a large covered tasting pavilion. It pours Chardonnay, Cabernet Sauvignon, Vidal Blanc, and a steady rosé, which makes it a good first stop for a group that wants a broad introduction to Maryland wine.

Linganore Wine Cellars in Mt. Airy is the state’s largest producer by volume, with a portfolio that runs from dry estate reds to semi-sweet fruit wines. There is live music most weekends and picnic space on the grounds. It works well for a group whose tastes land all over the sweetness spectrum.

Old Westminster Winery in Westminster is a natural-wine producer farming organically with minimal intervention. The pours are small-production, and the staff will explain what natural wine actually means in the glass: lower sulfites, native yeasts, sometimes a little oxidation. If anyone in your group has been curious about the style, this is a clean introduction to it.

Black Ankle Vineyards in Mt. Airy is the premium estate of the group, dry-farmed, focused on Bordeaux and Rhone varietals. The Cabernet Franc and the red blend called Crumbling Rock are the wines people talk about, and they tend to sell out each vintage. Smaller tasting room, higher ceiling than most Maryland producers.

Catoctin Breeze Vineyard up in Thurmont (Frederick County) sits near the Catoctin Mountain range, with cooler growing conditions and mountain views. It is the one to add when you want a longer day or a more remote final stop.

No designated driver, so everyone tastes

Every guest can taste at every winery, because your chauffeur is the driver. This is the core reason to book a chauffeured wine tour instead of taking your own car. The chauffeur drives the full day, stays with the vehicle at each stop, and drives you home at the end. No one nurses a single pour to stay sober for the road, and no one watches the clock for the trip back to DC. For a Maryland day this matters more than usual, because the wineries are spread across rural Carroll and Frederick County roads that you do not want to navigate after four tastings.

What tasting fees and lunch cost

Tasting fees at Maryland wineries run about $10 to $25 per person per winery, paid directly at each one. Some wineries credit the fee toward a bottle purchase; your chauffeur carries current information on which policies apply.

For food, Boordy has a cafe with cheese plates, charcuterie, and sandwiches on weekends. Linganore usually has food trucks or vendors on summer and fall weekends. Old Westminster and Black Ankle focus on wine over food but allow outside food on their grounds, and the town center in Mt. Airy has restaurants within about five minutes of both Linganore and Black Ankle if you want a proper sit-down lunch.

Maryland or Virginia wine country, which should you pick?

Pick Maryland for smaller estates, a quieter room, and a slightly different wine style, especially as a couple or small group focused on the wine itself. Pick Virginia (Loudoun County) when you want the largest concentration of wineries in one area and event-friendly tasting rooms, which tends to suit bachelorette parties and big weekend groups better. Both run from DC with the same chauffeured setup. If you are weighing the options, start at the wine country tours hub, then compare the full-day Virginia wine country tour against this Maryland route.

Best time of year to go

Late spring (May into June) and fall (September into October) are the best windows. Fall harvest in particular puts the estates at their best, and some wineries add barrel tastings or harvest events. Summer is fine but gets hot, and a few of the smaller producers trim their hours during the hottest weeks. Winter pours are quiet and intimate but check ahead, since some tasting rooms cut weekday hours. Whatever your date, we call ahead to confirm what is open and happening before the tour.

Pricing

Wine tours carry a 6-hour minimum in every vehicle. Starting at $660 for 6 hours for two guests in the executive sedan (up to 3 guests), $720 in an Executive SUV (1 to 6 guests, $120/hr beyond that), and $840 in a Mercedes Sprinter Van for groups up to 13 ($140/hr beyond). Tasting fees ($10 to $25 per person at each winery) are paid at the winery. Book online or call (202) 609-9811.

Related wine country tours

Maryland is one of two wine regions we run from DC. See the wine country tours hub for the full lineup, including the Virginia wine country tour and the open-format wine tasting tours. Tasting fees and food are paid at each winery directly.

Book this Maryland wine tour from DC

Call (202) 609-9811 or book online. An expert answers 24/7, no voicemail. Fall weekend dates at Black Ankle and Old Westminster fill quickly, so book 2 to 3 weeks out if you have a specific date in mind, and tell us your taste profile so we can line up the right three wineries.