Green Hill Winery is part of the cluster of wineries in the countryside around Middleburg, the historic town at the heart of Virginia's hunt country. The landscape here is stone walls, horse farms and rolling pasture, and a winery visit in the Middleburg area is often as much about the drive and the setting as the wine.
For visitors coming from Dulles, DC or the Northern Virginia suburbs, the trip is easy enough to plan but long enough that the ride home deserves some thought. This guide covers how to reach Green Hill Winery, how to time a tasting day, how to pair it with Middleburg itself and why a chauffeur is the simplest way to do it.
Where Green Hill Winery Is
Green Hill Winery is in the Middleburg area, west of Aldie and the Route 50 corridor that runs out from Fairfax and South Riding. Middleburg straddles the line between Loudoun and Fauquier counties, and many of its wineries sit on rural roads off Route 50 or the country lanes north and south of town.
Because rural addresses around Middleburg can be confusing, and map apps sometimes route visitors down unpaved farm roads, give us the winery's exact street address from its official website when you book. Your chauffeur will plan the approach in advance.
Getting There From Dulles, DC and Northern Virginia
From Dulles Airport, Middleburg is about 32 miles away, and the drive typically takes 40 to 50 minutes. The usual route heads south and west to Route 50, then west through Aldie into hunt country. Route 50 narrows to a two-lane road west of the suburbs, passes through Aldie's small historic village and continues into Middleburg's main street.
From Fairfax, Chantilly and Centreville, the drive is similar or a little shorter. From Arlington, Alexandria or DC, plan on an hour or more each way, depending on I-66 traffic. On fall weekends, Route 50 west of the suburbs can back up, especially around Aldie and through Middleburg, where the speed limit drops and traffic slows for pedestrians in town.
Country Roads and Gravel Lanes
Many wineries in this area are reached by narrow roads, some of them gravel, with blind curves, horse trailers and riders on the shoulder. These are pleasant roads to be driven on and less pleasant to drive yourself after several tastings. Coming home after dark in late fall, when deer are active, is when a professional driver makes the biggest difference.
Check With Green Hill Winery Before You Go
Tasting hours, reservation requirements, group size limits, food, live music and policies on children and pets are all set by the winery and can change by season. Check Green Hill Winery's official website or contact them directly before you plan, especially for a larger group, a private event or a fall weekend visit. Once you know your arrival time, book your car around it.
Planning a Green Hill Winery Day Trip in Virginia Hunt Country
Most visitors pair Green Hill Winery with one or two other stops and some time in Middleburg. A typical day might start with a late-morning tasting, continue with lunch in town and end with a second winery in the afternoon.
- Departure: leave the Dulles area about an hour before your first reservation; leave earlier from DC or inner Northern Virginia.
- First stop: plan on an hour or more for a tasting, longer if you settle in with food or a bottle.
- Middleburg: the town's main street has shops, galleries and restaurants, and makes a natural midday break.
- Second stop: other wineries around Middleburg, Aldie and The Plains are usually a short drive apart on country roads.
- Return: allow 40 to 50 minutes back to Dulles and more on a Sunday evening heading east on Route 50 or I-66.
Combining Your Tasting With Middleburg
Middleburg is small enough to walk end to end in a few minutes and pretty enough that most visitors want to. Its main street, Washington Street, carries Route 50 through town, lined with historic buildings, boutiques, tack shops and places to eat. The Red Fox Inn, one of the oldest inns in the region, is in the center of town, and Salamander Resort sits on the edge of it.
With an hourly booking, your chauffeur can drop you on Washington Street, wait while you walk and shop, and pick you up again for the next winery. That avoids the hunt for a parking space in town on a busy Saturday.
Hourly Service or Separate Transfers
Hourly Service
With hourly, as-directed service, the chauffeur and vehicle stay with you from pickup to drop-off. You can change the order of stops, stay longer where you like and leave when you're ready. For a day that includes Green Hill Winery, lunch in Middleburg and a second stop, hourly service is usually the best fit.
Transfers for Overnight Guests
If you're staying in Middleburg overnight, two one-way transfers often make more sense: one from Dulles or home to your hotel or inn, and one back the next day. Guests flying in for a hunt-country weekend can be met at Dulles; airport pickups include 45 minutes of complimentary waiting on domestic arrivals and 60 minutes on international arrivals, timed from touchdown.
Celebrations, Groups and Wedding Guests
Hunt-country wineries are popular for birthdays, anniversaries, bachelorette parties and rehearsal events, and many couples marry at estates around Middleburg. If you're coordinating transportation for a group or wedding guests, tell us the number of people, the venues and the timing, and we'll recommend a plan. Our Middleburg wedding limo page has more on guest shuttles and wedding-day service.
The Seasons in Hunt Country
Each season changes the feel of a winery day around Middleburg. Spring brings green pastures and point-to-point races on weekends across the hunt country. Summer afternoons are long and warm, and shaded seating fills early. Fall is the busiest season, with harvest, foliage and crowds on Route 50, so reservations, both at the winery and for your car, matter most from September through November.
Winter is quieter. Some tasting rooms keep shorter hours, and the drive home is in the dark by late afternoon, which is one more reason to let someone else handle the country roads. Whatever the season, check the winery's current hours before you set your pickup time.
Choosing a Vehicle
For a couple, a Business Sedan such as a Mercedes-Benz E-Class or a First Class Sedan such as a BMW 7 Series or Mercedes S-Class suits the drive along Route 50. Two couples often choose a Chevrolet Suburban, which seats up to five, or a Lincoln Navigator for up to six. Larger groups can travel together in a Mercedes Sprinter with seating for up to thirteen. If you plan to buy cases of wine, let us know so we leave room.
What to Bring
Wineries in hunt country are mostly outdoors, with lawns, patios and gravel paths. Bring a layer for cool afternoons, sun protection in summer and comfortable shoes. Every guest who plans to taste must be 21 or older with valid ID. A phone charger and a bottle of water for the ride are worth packing on a full day.
Booking Your Ride
Fall weekends in Middleburg book quickly, especially for groups. Reserve as soon as your winery plans are set. Sedans and SUVs can be cancelled free of charge up to 3 hours before pickup, and Sprinter vans and special-event bookings up to 12 hours before. Your quote is all-inclusive, covering tolls, taxes and gratuity.
Book online through our reservation page or call (877) 609-1919 any time. Tell us your pickup address, the wineries you'd like to visit and how many people are coming.
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Frequently Asked Questions
Where is Green Hill Winery in Virginia, and how far is it from Dulles?
Green Hill Winery is in the Middleburg area of Virginia hunt country. Middleburg is about 32 miles from Dulles, typically 40 to 50 minutes via Route 50. Allow extra time for weekend traffic through Aldie and Middleburg and for the country roads to the winery.
Does Green Hill Winery require reservations?
Reservation rules, hours and group policies are set by the winery and can change by season. Check Green Hill Winery's official website or contact them directly before you visit.
Can we stop in Middleburg between wineries?
Yes. With an hourly booking, your chauffeur can drop you on Washington Street, wait while you walk, shop or eat, and take you on to the next winery.
Can you pick up guests flying into Dulles for a weekend in Middleburg?
Yes. Airport pickups include 45 minutes of complimentary waiting on domestic arrivals and 60 minutes on international arrivals, timed from touchdown, and we track your flight.
What vehicle fits two couples on a winery day?
A Chevrolet Suburban seats up to five and a Lincoln Navigator up to six, with room for any bottles you buy. Larger groups can use a Mercedes Sprinter for up to thirteen.