Best Things To Do In Middleburg VA On A Day Trip

With so many things to do in Middleburg VA, it’s no wonder that folks from Washington DC often turn an excursion to this charming town into a fun-filled day trip.

Steeped in history and surrounded by rolling hills, wineries and bucolic horse farms, Middleburg offers something for everyone.

And I do mean something for everyone!

Whether you’re a history lover, a high-end shopper, a wine drinker or a horse enthusiast, a day trip to Middleburg VA should be on your travel bucket list.

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A Middleburg VA day trip is great, but turn it into a weekend getaway by booking a night at historic Welbourne Inn. (This is my absolute favorite Bed and Breakfast)!

Things To Do In Middleburg VA For History Lovers

For the history buff, Middleburg, Va. features buildings that pre-date the American Revolution.

The entire town and surrounding area went on to play a key role in the Civil War when it was the scene of the Battle of Middleburg in 1863.

Rolling hills and eighteenth-century architectural treasures are a definite draw to this unique village in northern Virginia.

Even though it’s a very small town, Middleburg has more than 160 buildings listed on the National Register of Historic Places. Just walking the streets and looking at the architecture (especially the huge stone buildings), is fun to do on a day trip.

The history of Middleburg is also pretty amazing. It was established in 1787 by American Revolutionary War Lieutenant Colonel and Virginia statesman John Leven Powell.

Powell purchased the property from Joseph Chinn, a cousin of George Washington.

Related Post: Everyone should visit George Washington’s Mount Vernon estate once in their lifetime!

Powell changed the name from “Chinn’s Crossroads” to Middleburg because of its location halfway between Arlington and Winchester on the Ashby Gap trading route (now Route 50).

Brick sidewalk in Middleburg VA with storefronts in the background.
Brick sidewalks give Middleburg a charming look.
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Things To Do In Middleburg VA For Shoppers

I’ve heard people call Middleburg VA, “The Rodeo Drive of the East.” That should give you an idea of the quality of the shopping in Middleburg.

A shopping trip to Middleburg is more than buying something — it’s an adventure. Whether you’re just browsing or hunting for the perfect treasure, it’s all part of the fun.

There are numerous shops, boutiques, high-end clothing stores and even tack shops. If you’re looking for toys, clothes, farm items, riding apparel, real estate or anything in between, you’ll find it in Middleburg.

Another nice thing about shopping in Middleburg is that everything is conveniently located in a condensed area, so walking is a breeze.

In fact, within just a few block radius, shoppers can find everything from boutiques and antique shops to upscale clothing, fine art galleries and equestrian stores. (You can literally buy a high-end men’s suit, an expensive work of art, or a bag of oats for your horse, all on the same street).

Ready to splurge on a room? Check out the Salamander Resort and Spa.

One of my favorite Middleburg shops is Creme de le Creme, which features all sorts of home goods, stationery, decor, and some of the best smelling candles I’ve ever come across.

Of course, I love antiques, so a stop at the Middleburg Antique Gallery is a must for me. With 45 dealers, they have a little bit of everything,  including formal English, European and American furniture in mahogany, walnut and English Oak. They also carry art, jewelry, Oriental rugs and old books!

On the other end of the shopping spectrum is the Community Shop Consignment and Thrift. Personally, I love “searching for treasures” in thrift shops, and there are gems to be found here. You never know what you will find on consignment (even antiques), so put this shop on your Middleburg Va day trip list!

The Fun Shop is fun! If you need a unique gift for someone, this is the place to go. They specialize in Hunt Country gifts, home decor, children’s toys, books and kitchen and gourmet items.

No matter what time of year you’re in Middleburg Va, The Christmas Sleigh is a festive store to browse in with wall-to-wall Christmas decor. A lot of the items are authentic German ornaments or figurines, so it’s on the high-end as far as pricing.

The Christmas shop in Middleburg VA is open all year round. It's a round door surrounding by greenery.
The Christmas Sleigh in Middleburg is open all year.

Brick and Mortar Merchantile is just one of those shops where you have to look at everything. They carry lots of Virginia products like peanuts and hot honey, as well as a mix of unique gifts.

Even though I no longer own a horse, I still enjoy going to The Tack Box. They feature saddlery and riding attire, but also equestrian gifts, so if you have a horse lover on your gift list, this is the place to go.

There are lots of other places to shop during a Middleburg VA day trip, but you get the idea. This town is a shopper’s paradise!

Where To Dine In Middleburg VA

Shopping is exhausting! You will definitely need somewhere to relax and re-charge with a good meal at a Middleburg restaurant.

Luckily, Middleburg VA will not disappoint in this category either.

My first recommendation is the Red Fox Inn, and frankly, I didn’t know whether to list this under the History section or the Food section, because it fits in with both.

In addition to serving food, the Red Fox “Inn” has been a place to book a good night’s sleep since 1728! (So if you want to turn your Middleburg day trip into a weekend getaway, you’re in luck).

Back to the history of the Red Fox Inn, General J.E.B. Stuart and Colonel John Mosby, commander of Mosby’s Rangers, were known to frequent the tavern during the Civil War, but other notables have visited the Inn as well.

Read about Mosby Ranger Joseph Bryan who fought around Middleburg during the Civil War.

Some of these include President John F. Kennedy, who held a press conference in the upper Tavern, and Jacqueline Kennedy Onassis who often overnighted at the Inn while on fall foxhunting holidays.

Still others include Elizabeth Taylor and U.S. Senator John Warner, who often dined in the tavern during their courtship and after their marriage.

Hollywood notables who entertained friends there, include Joann Woodward, Paul Newman, Tom Cruise, and Robert Duvall.

See why I love this Tavern? They also have a special four-course seasonal dinner that I’ve heard is very good.

If the Red Fox Inn isn’t your cup of tea, you have plenty of other options.

The King Street Oyster Bar fills up quickly, so reservation

The Oyster Bar in Middleburg VA is a historic building with 4 pillars.
The King Street Oyster Bar in Middleburg.

The Old Ox Brewery is a nice spot with live music, and the Red Horse Tavern has a beautiful patio if you want to sit outside.

Things To Do In Middleburg VA For The Wine Lover

When you’re done with a morning of shopping or exploring, you might want to relax with a glass of wine. Northern Virginia has become a mecca for wine lovers and Middleburg is in the center of wine country.

In fact, there are more than 20 wineries within a 30 minute drive of Middleburg, making it one of the top 10 wine destinations in the world.

One advantage that the Middleburg area has over other places is that you get to sip wine while staring at the the beautiful Blue Ridge Mountains. The views are incomparable!

Greenhill Winery is a boutique winery located in a farm winery setting. They feature 100 percent Virginia wines and offer Charolais beef and honey from their apiaries at the Farm Store.

Boxwood Estate is owned by John Kent Cooke, former owner and president of the NFL Washington Redskins.

Other wineries that are close to Middleburg are Chrysalis50 West, and Cana Vineyards.

If you’re more into spirits, Middleburg has you covered there too. Mount Defiance Cider and Distillery is located on Washington Street, so you don’t even have to leave town!

Horses and hounds parade down the street in Middleburg, Va. The Christmas parade in Middleburg is unlike any other in the world.
Horses and hounds parade down the street in Middleburg, Va. The annual Christmas parade in Middleburg is unlike any other in the world.

Things to Do In Middleburg VA For The Horse Enthusiast

You can hardly drive anywhere around Middleburg, Va. without running into someone on horseback or a pack of hounds, so its not hard to figure out why it’s known as the nation’s Horse and Hunt Capital.

The equestrian community is a huge part of the culture of this charming Southern town. Located within Middleburg is the National Sporting Library and Museum, which offers a world-class research library and fine art Museum highlighting the rich horse heritage of the area.

Founded in 1954, the National Sporting Library & Museum covers every aspect of horsemanship including shooting, steeplechasing, foxhunting, flat racing, polo, coaching, and wildlife.

It’s located on a six-acre campus and has a vast collection of rare book holdings, archives and art collection.

Home To The Rich And Famous

The Middleburg area is well known for attracting wealthy celebrities and the wealthy.

The list of notables who have or had) homes in the Middleburg and Upperville areas include: Washington Redskins owner Jack Kent Cooke, Sen. John Warner (R-Va.), a smattering of du Ponts, the Bertram Firestones (she’s a Johnson & Johnson heir), Paul Mellon and Washington Post publisher Donald E. Graham.

Others include actor Robert Duvall and comedian Dick Smothers.

Small Town Charm In Middleburg, Va.

Located in western Loudoun County, Middleburg, Va. feels like it’s a lot farther away from Washington, D.C. than just an hour.

But this charming historical town is an easy and scenic drive that makes a great day trip. It’s also right next door to Aldie, VA., where you can stop and tour the historic mill.

Another plus for those seeking to get away from it all on a Middleburg VA day trip, is that this quaint colonial village has no fast-food restaurants and just recently added a stoplight.

That’s not say it doesn’t get crowded with shoppers and out-of-town visitors on the weekends. But even when it’s crowded Middleburg retains its small-town character and offers plenty of fun experiences.

Christmas in Middleburg VA

Oh my, Christmas in Middleburg, Va. is an event not to be missed. The historic village takes on all the charm of a wintery postcard and exudes Christmas charm at every turn.

Thousands line the streets for this family tradition that includes local hunt clubs, horses, hounds –and of course, Santa!

The Christmas in Middleburg celebration also includes a tree lighting, a Christmas parade, shopping, caroling, and much more.

Mark your calendar for the first Saturday in December and plan to get into the Christmas spirit.

Need A Place To Stay In Middleburg?

Wrap-Up Of Things To Do In Middleburg Va

I love visiting Middleburg, and have explored every inch of northern Virginia, from the Arlington House to Long Branch Farm and the small town of Waterford.

I’ve even toured private homes that were Mosby Safe Houses like Belle Grove and Green Garden when doing research for my Civil War Trilogy Shades of Gray.

If you don’t know who Mosby was (or why he had “safe houses”), you can learn more about this real-life soldier that I based the the main character in my Civil War novel is based upon.

Getting To Middleburg, Va.

Even though it seems a million miles away, Middleburg, Va. is conveniently located about 35 minutes from Dulles International Airport and 45 miles from Washington, DC. and Reagan National Airport.

Things To Do Near Middleburg VA

Visit Upperville VA

Since Upperville VA is right up the road from Middleburg, it makes a nice scenic drive check it out. (Don’t blink or you’ll miss it).

The Hunter’s Head Tavern is the go-to place to eat in Upperville. I dined there during the summer and sat outside. The food is fresh with most of it being sourced from local farmers.

Visit Aldie VA

If you like history, then you’ll love the village of Aldie, which is famous for its historic mill. There are lots of Civil War stories associated with Aldie, including many about Colonel John Mosby.

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