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Road Trip on U.S. Highway 50 – A Trip Through Charming Towns into Northern Virginia

Discover charming towns, colonial-era history, and awesome places to eat, sleep, and play along this road trip on U.S. Highway 50.

By Jason Barnette | Travel writer and photographer with 15+ years of road tripping experience

Located on these road trip routes:

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It was an old road, and driving old roads tends to be the most fun. Leaving Winchester behind, I traveled along the two-lane U.S. Highway 50 through charming small towns steeped in colonial history. A few outdoor adventures, some fantastic wineries, and some really great food kept me going on this short road trip – it might keep you going for much longer.

The first time I drove U.S. Highway 50 was westbound out of Washington, D.C. I could see the Blue Ridge Mountains ahead for miles. During that first trip, I made it as far as Paris before turning off the road.

Three years later, I returned to U.S. Highway 50. After spending a couple of days in Winchester, I hit the road toward Alexandria. It was a day of adventure, shopping, and dining that has left an impression on me ever since. It’s a short drive – I did it in just a single day – but it’s a route I could spend an entire three-day weekend enjoying. In fact, that’s exactly how I think you should enjoy it.

Road Trip Map

Get all the details at a glance to help plan the road trip. Use the map below to see the route and save it to your smartphone to use on the road trip.
Winchester, VA
Arlington, VA
67 miles
total distance
2-5 nights
suggested duration
itinerary stops

How to use this map: Click the icon in the top-left corner to open the Map Legend, then click on any of the legend items to display more information. If you have a Google account, click the star beside the map’s name to save this map to your account, then access the map from your smartphone during your trip.

Old Town is pedestrian-only, making it a peaceful and safe place to explore.
No. 01

Winchester, Virginia

When the Virginia House of Burgesses granted a city charter to Winchester in 1752, it was only the fourth city established in the colony. Today, Winchester is known as the “Apple Capital,” but I will always remember the city for Old Town.

Spanning two very long blocks in the middle of the city, Old Town features centuries-old architecture, fantastic local dining, and great places to shop along a pedestrian-only brick street. It’s where I spent the majority of my two days in Winchester – although there were a few other things to do in town.

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The Snow White Grill was an interesting place to grab lunch – three bite-size cheeseburger sliders in a narrow classic diner style. Of course, I ended up at Roma Wood-Fired Pizzeria for dinner – their Sausage Rustica pizza was amazing, and they serve craft beers from Alesation Brewing. The Union Jack Pub & Restaurant and Village Square Restaurant had fantastic menus but what I loved most was their comfortable outdoor seating.

Thinker Toys features “toys you don’t find in the traditional big-box store.” Inside, I found lots of quirky toys, but my favorite section was an entire wall of interesting board and card games! At Winchester Book Gallery, I found an inspiring book about road trips – it made me wish I had written the book first – along with new releases, local interest, and lots of history books. Mountain Trails was a great place to find clothing, gear, and accessories for your next outdoor adventure.

To end my time in Old Town, I needed some coffee. Java Kava was an interesting place to grab a coffee – although I did not try any of their kava juice made from a South Pacific root.


READ MORE: 50 Road Trip Quotes to Inspire Your Next Adventure + Downloadable Social Media Images

Winchester has been part of a lot of America’s history, and you can learn all about it at several fantastic museums. The Shenandoah Valley Civil War Museum is located inside the old courthouse in Old Town – the museum features lots of exhibits and a renovated courtroom to explore. At George Washington’s Office, visitors can meander through the rustic log cabin where Washington set up an office while building Fort Loudon and learn about his long history in Winchester. A guided tour at Stonewall Jackson’s Headquarters detailed his time fighting through the Shenandoah Valley during the Civil War. But my personal favorite historic home to tour was Abram’s Delight – built in 1753, a guided tour of the two-story stone house included a trip to the basement.

Winchester-Frederick County CVB 1400 South Pleasant Valley Road, Winchester, VA | 540-542-1326 |

Where to Stay in Winchester

There are many great hotels in Winchester, with most of them located along Interstate 81 at the commercial end of town. Any of these hotels would be a great choice, and downtown is just five minutes away.


but it does feature very well-appointed guest rooms. Choose from rooms with one or two beds.

Red Roof Inn is simple, affordable, and that bad at all. With recently renovated rooms to include faux hardwood floors and all-new furniture, Red Roof is proven road trip ready. Choose from rooms with one or two beds – but my recommendation for travelers is the Superior King or Deluxe King.


Hampton Inn is always a great choice, with the best free breakfast you’ll ever find at a chain hotel. The outdoor swimming pool isn’t exactly peaceful with its location beside the interstate exit, but the rest of the hotel is comfortable. Choose from rooms with one or two beds or a suite with a bed and sleeper sofa.


The George Washington is the only downtown hotel – and it’s absolutely worth the stay. It’s more expensive than most hotels in town, but not by much. The amenities make up for the extra cost, including a swimming pool and hot tub, on-site restaurant and lounge, and walking distance to Old Town. Choose from rooms with one or two beds, and they also have a suite with a bed and sleeper sofa.

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John Mosby Highway

U.S. Highway 50 is one of the longest roads in the country – it stretches just over 3,000 miles from Ocean City, Maryland, to West Sacramento, California. It was one of the original routes of the U.S. Highway System created in 1926.

From Winchester to Chantilly, the road is called the John Mosby Highway. Mosby was a colonel in the Confederate Army during the Civil War, leading a cavalry for the 43rd Battalion – also known as Mosby’s Rangers. After the Civil War, Mosby served as consul in Hong Kong and a lawyer in several positions.

Leaving Winchester, the road is initially a four-lane divided highway. Shortly after passing the Sky Meadows State Park entrance, the road shrinks to a pleasant two-lane road through the countryside. The two-lane road continues almost to Chantilly.

National Park Week 2024

Learn about the annual celebration of the National Park System and read my travel guides to national park units across the country.

The gorgeous entrance to the Quarters – and a frequent backdrop for portraits.
No. 02

State Arboretum of Virginia

In 1924, Graham Blandy willed 700 acres to the University of Virginia on the condition it be used to train college students in farming methods – and it was to be called the Blandy Experimental Farm. In 1986 – after four years of effort by the farm’s director Dr. Ed Conner – the State Arboretum of Virginia was founded, and the property opened to the public for the first time.

The 172-acre arboretum features over 5,000 trees – including the 300-tree Ginkgo Grove. The adventure begins at the parking area along Blandy Farm Lane. Several trails cut through the arboretum, offering a chance for leisure hiking that can take anywhere from half an hour to several hours.

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Start with a walk to the Quarters – a gorgeous brick building with an arched entrance that is a frequent backdrop for photo shoots. The Boxwood Garden is located in front of the Quarters along the entrance road. If you don’t feel up to hiking across the arboretum, you can drive along Wilkins Lane Loop Drive. There are several parking areas along the loop road – including one at the Hewlett Lewis Pavilion near a small lake.

400 Blandy Farm Lane, Boyce, VA | 540-837-1758 |


Ashby Gap

Ashby Gap is exactly what the name implies: a gap in the Blue Ridge Mountains between Northern Virginia and the state’s western reaches. It was named after Thomas Ashby, who settled the area after receiving a land grant for property along Goose Creek.

Passing through Ashby Gap on U.S. Highway 50 means leaving the mountains behind. But the first time I drove through the gap, I was heading west. Seeing the gentle rise in elevation from a distance and passing through the gap was an exciting affair – I was home in the mountains again.

The Ashby Inn & Restaurant is located inside a charming, two-story white house in a small community just off U.S. Highway 50. Each of the rooms in the boutique hotel is individually decorated and features a private bath. Common spaces include comfortable furniture with a patio featuring a gorgeous view of the countryside.

A full breakfast is included in the morning, and I’m certain they offer all the coffee you can drink. It would be a great start to a day exploring the region – or maybe you’re just passing through. Either way, you’ll sleep great at the Ashby Inn.

National Park Week 2024

Learn about the annual celebration of the National Park System and read my travel guides to national park units across the country.

No. 03

Sky Meadows State Park

The 1,860-acre Sky Meadows State Park offers an exciting opportunity to connect with nature on hiking trails, enjoy an afternoon picnicking, or learn the local history of colonial-era farming practices.

The Sky Meadows State Park Visitor Center is located inside the historic Bleak House. Built in the early 1800s by Abner Settle, the house sat in the middle of the farm tract established initially in 1731. Guided tours are offered inside the house that is furnished to represent a typical 1850s farmhouse.

The park features 22 miles of hiking trails – many of them connecting in and around the visitor center area. The 0.61-mile Piedmont Overlook Trail features a couple of nice scenic overlooks with views of the Virginia piedmont east of the Blue Ridge Mountains. Connecting to the end of the trail, the 1.1-mile Ambassador Whitehouse Trail climbs the mountain and connects to the Appalachian Trail.

The roughly 2,200-mile Appalachian Trail passes through the edge of Sky Meadows State Park. The park is a great place to spend a couple days hiking the AT. It’s about a twenty-mile hike south to Shenandoah National Park along a relatively level ridgeline – but inside the national park, the trail ascends nearly 1,800’!

11012 Edmonds Lands, Delaplane, VA | 540-592-3556 |

The gorgeous one-room Upperville Library.
No. 04

Upperville, Virginia

Rolling into Upperville was an unremarkable affair. Traffic was moving slowly on the two-lane highway – a small green sign announced the town’s entrance. It was evident just how old the route was, considering businesses were built almost at the road’s edge and ancient stone walls lined the street.

I was ready to admit this was just a pass-through town until I drove past the Trinity Episcopal Church. I quickly returned to the small parking lot, unsure if I had found something remarkable. The first church on this property was built in 1842 – and a second in 1895 – but neither of those structures exists today. From 1951 until 1960, the current church was built as a gift from Mr. and Mrs. Paul Mellon – the same couple saved the farm at Sky Meadows State Park from being developed.


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Leaving the car behind – surely it would be safe in a church parking lot – I walked down the street to the United States Post Office. It was one of the first – and only – times I captured a photo of a post office. The gorgeous one-story stone building with colonial-style columns was a fantastic photo op. On my way back to the car, I passed the Upperville Library – built circa 1804 in a cute one-story stone house with flower boxes beneath the window.

Just as I was about to leave town, I came across the Hunter’s Head Tavern. The gastropub is located inside a gorgeous two-story white house literally at the edge of the road – it couldn’t be easier to find on a road trip. Owned by nearby Ayrshire Farm, all the menu items use sustainable, local ingredients – the beer-battered fish & chips were amazing.


Goose Creek Stone Bridge

Built in 1810, the Goose Creek Stone Bridge is a 200-foot-long stone arch bridge spanning a small river. It was built for the Ashby Gap Turnpike – one of the first permanent roads built through Northern Virginia.

It’s a hidden gem that is entirely too easy to miss while road tripping along U.S. Highway 50. From the two-lane road, the view of the bridge is entirely hidden by dense trees and vegetation. Turn onto Lemmon Bottom Road and look for a dirt road. There, you will find an interpretive panel discussing the Attack at Goose Creek Bridge – and a view of the gorgeous bridge.

Shopping is a common activity in Middleburg – but it’s not the only thing to do.
No. 05

Middleburg, Virginia

In 1787, Middleburg was founded by John Leven Powell, a lieutenant colonel during the American Revolutionary War. He named the town after its location almost exactly halfway between Alexandria and Winchester along the historic Ashby Gap Turnpike – today known as U.S. Highway 50. In the early 1900s, the town became known as the “Horse and Hunt Capital” of the country for the popular sports of foxhunting and steeplechasing.

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Middleburg does not have a formal visitor center, but I found the National Sporting Library & Museum to be a great substitution. The museum is only open on Friday and Saturday. Still, it does a great job of telling the town’s compelling history with a fine art gallery and interpretive information.

I was delighted to find The Christmas Sleigh – a year-round retail shop dedicated to my favorite holiday. The Fun Shop was my kind of store with local interest books, home décor, and all sorts of fox and horse-themed items. The Middleburg Antique Gallery is home to dozens of antique dealers bringing everything from furniture to jewelry to the beautiful little retail space in town.


There are just as many restaurants in Middleburg as retail shops, so you won’t go hungry from a lack of options. King Street Oyster Bar had fantastic food at a great price – just over ten dollars for parmesan crusted trout – making it a great place for lunch. Red Horse Tavern had the best appetizer menu in town to go along with salads, burgers, and sandwiches. For dessert, I cannot stress how important it is to visit Scruffy’s Ice Cream Parlor for a double scoop of homemade ice cream in a bowl.

Finish your time in Middleburg with a couple of local breweries. Wild Hare Hard Cider Pub and Mt. Defiance Cidery offer tastings of hard ciders – my favorite kind of craft beer in autumn – in comfortable tasting rooms. Less than a block away from downtown, Old Ox Brewery has a tasting room and beer garden where you can sample the beer they make on-site.

Visit Middleburg


Where to Stay in Middleburg

There are only a few options to stay in Middleburg, but there are two I recommend above all others. Both are pricey, but each would be a wonderful weekend getaway.


The Red Fox Inn & Tavern is located downtown on the main drag – putting it within walking distance of all the shopping and dining. The boutique hotel is located inside a gorgeous four-story brick home. Most rooms include only a single bed – your choice between king or queen – but they have three suites with more beds and a sleeper sofa for traveling families.


The Salamander Resort & Spa is the pinnacle of overnight lodging in Middleburg – and maybe all of Northern Virginia. Pamper yourself with exquisite rooms with private terraces and balconies, take advantage of the three swimming pools, and enjoy a visit to the day spa. The gorgeous resort is just five minutes from downtown but feels like an oasis in the countryside.

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Middleburg American Viticultural Area

In 2012, the Middleburg American Viticultural Area was established in the valley between Interstate 66 and the Potomac River. An AVA is a geographical area where wine is produced from grapes grown within the AVA region. Surrounding Middleburg, the AVA covers 198 square miles in Fauquier and Loudoun Counties.

The Middleburg AVA originally included 23 wineries and 14 vineyards – and six of those are located along U.S. Highway 50. Slater Run Vineyards is located west of Middleburg near the Goose Creek Stone Bridge. The vineyard has a tasting room inside a gorgeous modern building with outdoor seating to enjoy the view. Boxwood Winery is located just south of Middleburg on a stunning property with views of the Blue Ridge Mountains in the distance. The tasting room – located inside a modern building with a stainless steel bar – is a great place to get their wine flights.

Greenhill Winery & Vineyards is the first you’ll pass after leaving Middleburg behind. The tasting room is located inside a two-story building with rustic farmhouse décor. You will definitely want to sit outside to appreciate the view of rolling hills on the property. Cana Vineyards & Winery is located on a small 43-acre farm just off the main highway. The tasting room is located inside a modern building – get a drink and sit outside in the connected gazebo with a view overlooking the vineyard.


50 West Vineyards is named after the main route of this road trip itinerary. It was a warm day when I visited the gorgeous modern tasting room – the large glass folding doors were open, connecting the interior with the patio. I only had fifty miles left to drive that day, so guess where I spent the rest of my evening?

READ MORE: The 27 Best Road Trip Quotes to Inspire Your Next Adventure

The tasting room at Chrysalis Vineyards is the most gorgeous in the area. The gravel driveway was a pleasant entrance to the vineyard – leading to a modern facility with a metal roof and stone walls. Do a tasting of their wines inside, but then take a glass outside to one of the covered pavilions with standing height tables made from old wine barrels.

The Briar Patch Bed & Breakfast Inn is a locally owned inn is situated in the heart of the Middleburg American Viticultural Area – making it a great place to spend a night or two and explore the wine country. The gorgeous farmhouse was built around 1805 and includes 8 bedrooms – two rooms have a private bath while the other six bedrooms share three bathrooms.

National Park Week 2024

Learn about the annual celebration of the National Park System and read my travel guides to national park units across the country.

No. 06

Aldie, Virginia

In 1765, brothers James and George Mercer built a grist mill along the Bellhaven Road west of Alexandria. By 1809, the road had been upgraded, and James Mercer’s son, Charles Fenton Mercer, established the village of Aldie named after his ancestral home in Scotland. The Ashby Gap Turnpike was completed in 1813, and a decade later, the village reached its peak population – a whopping 260 residents.

I knew I had rolled into a charming town when I passed the Aldie General Store & Café. Located inside a renovated two-story home, the interior featured hardwood floors and chalkboard walls covered in menu items. As I was heading in, Alicia, a day-tripper from Arlington, gave me a tip, “This is the best breakfast you’ll find in NOVA.”

I almost didn’t stop at the Little Apple Pastry Shop – it was hidden inside a charming, renovated house with a gravel parking lot – because I didn’t know they made the best apple pies. Beyond the delicious pies, they also offered cupcakes, cookies, and pastries perfect for road trip snacks.

At the edge of town, I found the Aldie Mill Historic Park. Maintained by NOVA Parks, the historic site is centered around the restored Aldie Gristmill. It’s only open on weekends from spring through autumn, but during those times, you’ll find a lot of activities and living history reenactments.

Just like that, my time in Aldie had come to an end. But it was a stop along a road trip I’ll never forget.


Where to Stay in Aldie

The charming Little River Inn is located in a two-story house on U.S. Highway 50 in Aldie. Parking is in the rear along a gravel driveway, where you’ll immediately feel at peace. The Main House features five bedrooms – two bedrooms have a private bath while the other three share a bath. The Patent House – a small one-story house next door – includes a double bed, full bath, and living room. The Log Cabin along the driveway features two bedrooms, one full bath, and a living room.

Evenings are often time spent on the wrap-around covered porch – comfortably hidden behind a row of hedges. A full breakfast is served every morning for guests in the small and cozy dining room in the Main House. It’s a great place to spend a night or two – especially if you explore the vineyards and wineries in the area.

After visiting George Washington’s Office in Winchester, tie it all together with a visit to Mount Vernon.
No. 07

Northern Virginia

Although Northern Virginia – locally called NoVa – includes Loudoun County and Middleburg, it doesn’t become apparent you’re entering the most densely populated area of the state until you roll into Chantilly. After 21 miles of two-lane road tripping adventures through charming small towns, John Mosby Highway widens into a divided highway and increases traffic congestion. 

George Washington’s Mount Vernon is the best place to learn about the life of George and Martha Washington. The original house was built by Augustine Washington and expanded into the mansion we can visit today by his son, George Washington. While Washington’s adult life began with land surveying in Winchester, it ended with simple farm life at Mount Vernon.

One of the best ways to explore Alexandria – especially for first-time visitors like myself – is the “Key to the City Attractions Pass.” For $20, the pass includes access to 9 historic sites throughout the city that includes Mount Vernon, the George Washington National Masonic Memorial, and Gadsby’s Tavern Museum. It’s a fantastic introduction to the city’s history and an entertaining way to spend a weekend.

In Arlington, U.S. Highway 50 wraps around Arlington National Cemetery. The cemetery is the final resting place of two presidents – William Howard Taft and John F. Kennedy – along with the Tomb of the Unknown Soldier.

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Do you have a question about travel or road trips? Are you a CVB or DMO interested in working with me? I typically respond to emails within 24 hours. Quicker if you include a good riddle.
Do you have a question about travel or road trips? Are you a CVB or DMO interested in working with me? I typically respond to emails within 24 hours. Quicker if you include a good riddle.

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