Jacqueline Kennedy Onassis loved Middleburg and so will you. Get your bags ready! This list of the best things to do in Middleburg, Virginia will make you want to start planning your trip today.
Middleburg, Virginia is located about an hour’s drive west of Washington, DC. It’s a perfect day trip from the city or a perfect weekend escape.
Middleburg has scenery, history, wineries, shopping, and delicious eats. This all combines to make Middleburg a destination worthy of your bucket list.
Read on for the best things to do in Middleburg, Virginia!
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1. Take in the picturesque scenery
When you visit Middleburg, you’ll want to carve out time just to drive around the countryside.
Middleburg is nestled between the Bull Run Mountains and the Blue Ridge Mountains. These mountains provide picturesque views of the surrounding countryside.
Rolling green hills are divided by stone walls and wooden fences. Cows and horses graze in the bucolic setting.
Surrounding the rolling green hills are gorgeous forests. These forests bloom with flowers in the spring and turn stunning colors in the fall.
When planning your drive, allow for plenty of time to take pictures. You’ll be pulling over constantly to take a pic of the beautiful scenery!
2. Eat *all* the delicious food
Rural Virginia might not be the first place you think about for a fantastic meal. But that will change after you visit Middleburg!
Middleburg has multiple restaurants that are phenomenal. You’ll find yourself adding extra meals to your day just to experience these restaurants!
I highly recommend including the Red Fox Inn & Tavern as one of your culinary experiences. Their prix fixe meal will go down in history as one of my favorite meals of all time.
If you’re looking for more casual fare, I recommend the Red Horse Tavern for their burgers. And be sure to check out King Street Oyster Bar for their daily happy hour from 3-6:30 pm.
Red Bar Sushi offers awesome sushi. And two Thai restaurants located directly across from each other (Best Thai Kitchen or Thaiverse) just beg you to try both and vote for your favorite.
If you love the dining experience as much as you love the food, then check out the restaurants at the Goodstone Inn & Restaurant and the Salamander Resort & Spa. Both offer world-class dining experiences within luxurious hotel settings.
3. Explore historic areas
You can’t come to Virginia and not geek out on some of the history that occurred here!
Middleburg’s historic downtown area includes some colonial-era buildings. One of the most notable buildings is the Red Fox Inn & Tavern. The inn was established in 1728. It is the oldest continuous running inn in the United States! At a minimum, stop inside to check out the tavern. You’ll feel like you stepped back in time.
Middleburg was also the site of two Civil War skirmishes during the Gettysburg Campaign. You’ll see gray metal signs just east of Middleburg to commemorate the location of these skirmishes.
4. Experience spectacular wineries
In recent years, Virginia has really stepped up its wine game. Winegrowers have become more experienced in growing grapes in Virginia. And maturing vines have started to produce exceptional wines.
But you really shouldn’t take my word for it. You should experience it yourself!
There’s nothing quite like sitting back with a glass of wine and a view of the rolling mountains in front of you. Just thinking about it has a calming effect on me.
Each of the Middleburg wineries has spectacular wine, so I’ll take a little time to talk about the other amazing characteristics of the wineries!
I recommend Greenhill Vineyards for the life-changing cheese boards. Popular Cana Vineyards has a festive weekend crowd. Boxwood Winery allows you to take a scenic stroll through the vineyard. Chrysalis Vineyards has a gorgeous hilltop view. And 50 West Vineyards has a wonderful, laid back atmosphere.
Visiting the Middleburg wineries is an experience in itself. Be sure to check out this article to plan an incredible trip to the Middleburg wineries.
5. Relax at luxurious accommodations
Middleburg is known for its luxurious accommodations. The town has three primary options for accommodations. While each of the options is fairly pricey, they all offer fantastic experiences:
- Red Fox Inn & Tavern: The Red Fox Inn & Tavern is a historic inn that was frequented by Jacqueline Kennedy Onassis. It is located in downtown Middleburg, making it easy to walk to local restaurants and shops. Even if you don’t stay here, I recommend dining at the amazing restaurant.
- Goodstone Inn & Restaurant: The Goodstone Inn & Restaurant offers guest rooms in six different buildings, from stately manor houses to adorable cottages. The buildings are spread across a beautiful 265-acre estate with rolling hills, farmland, and forest.
- Salamander Resort & Spa: The Salamander Resort & Spa opened in 2013 as a luxury getaway. It offers a wonderful variety of activities. You’ll find activities like equestrian programs, zip-lining, axe throwing, and art classes. Plus, the resort will provide transportation to and from local attractions.
If you’re looking for less pricey accommodations, you’ll need to stay about 30 minutes away in Leesburg, Virginia. Less expensive options in Leesburg include the Hampton Inn & Suites and the Homewood Suites by Hilton.
6. Don’t forget the other beverages
Wine isn’t the only beverage that Middleburg does well! Cider, craft brews, coffee, and smoothies await you in Middleburg.
Stop by Old Ox Brewery for a delicious craft brew. They have a regular rotation of seasonal beers. Ask for 4 ounce pours to create your own flight of awesome brews.
Mount Defiance Cidery & Distillery has two locations in Middleburg. In historic downtown, the cozy tasting room gives you a personalized tasting experience of high-quality spirits. On the east side of town, the barn offers a more energic crowd ready to sample all the ciders. I recommend you visit both locations to enjoy each experience!
Let’s not forget about the delicious caffeinated beverages! In the mornings, you’ll find people heading to Common Grounds. There you can sample their incredible coffees and breakfast foods.
If you’re craving some fresh juices or a smoothie, then Greenheart Juice Shop is calling your name. While you’re there, pick up some of the fantastic granola.
7. Browse adorable shops
Middleburg’s historic downtown is lined with adorable shops that are just begging to be explored. Here are some of my favorite shops:
- The Christmas Sleigh: It is Christmas 365 days a year at this shop! Authentic European ornaments await you inside.
- Crème de la Crème: You’ll want to redecorate your home after browsing through this store! The French and Italian home decor is unbelievable.
- Natured Composed: This is so much more than a flower and garden shop. The nature-inspired gifts give the shop a meditative air that you have to experience.
- Lou Lou: This boutique now has multiple locations throughout the U.S. And Middleburg is where it all began! Check out the original location when you visit.
8. Visit a one-of-a-kind museum
Middleburg, Virginia is at the heart of Virginia’s hunt country. The area has a rich history in raising horses and hounds, horsemanship, and horse racing.
This rich history is celebrated at the one-of-a-kind National Sporting Library & Museum. At this museum, you’ll discover art and narratives that describe the evolution of horse racing.
I found this museum to be fascinating. I’ve never experienced anything like it. Since it’s a relatively small museum, you can easily explore it in a short amount of time. It’s well worth the visit.
9. Celebrate Christmas in Middleburg
Middleburg has some seriously cool events during the year. One of these events is Christmas in Middleburg.
With Christmas in Middleburg, you can experience not one but two Christmas parades in one day! The first parade is called the “Middleburg Hunt & Hounds Review”. Horseriders and hounds trot down Washington Street during this parade. The second parade is a more traditional Christmas parade with floats.
But that’s not all! After the parades, you’ll find food and beverage tastings at locations all around town. There’s a craft fair all day long and Santa makes several appearances!
You’ll need to plan in advance to attend Christmas in Middleburg. Middleburg is a small town that is serviced by a two-lane highway. That means traffic can accumulate quickly on festival day. Plan on staying Friday night in Middleburg or arrive super early on Saturday morning. If you’re coming on Saturday, buy parking in advance so you’re not caught without a parking spot.
10. Explore magnificent horse farms
Middleburg and the surrounding area is known for its tradition of raising horses.
And once a year, you get a chance to explore these horse farms on the Hunt Country Stable Tour!
Every May, Trinity Church in Upperville, Virginia organizes a stable tour of horse farms and facilities. The tour takes you through Middleburg, Upperville, and The Plains, Virginia.
This is an incredibly unique event. You’ll want to get your ticket in advance!
I hope this list of the best things to do in Middleburg, Virginia has inspired you to visit! It’s a phenomenal town. I’ll see you there!
Comments or Questions?
Have a comment or a question? I’d love to hear from you! Visit me on Instagram @eastbymidwest and leave a comment or DM, or send me an email at pam@eastbymidwest.com.
