Top Things to Do in Middleburg, VA | Loudoun County

Top U.S. Travel Blogger Alicia Tenise at Greenhill Vineyards in Middleburg VA | Top Things to Do in Loudoun County

Are you looking for a fun and exciting weekend getaway or day trip from Washington, D.C.? Look no further than Middleburg, VA, and the surrounding Loudoun County area.

From outdoor activities to delicious eateries, the possibilities are endless. Whether you’re a Virginia native or a first-time visitor, you’ll discover many things to do in this historic town and its picturesque surroundings.

In this travel guide, we’ll look at the top things to enjoy in Middleburg and Loudoun County – from wineries and shopping to some of the best restaurants in the area and more. So grab your sun hat and a glass of vino, and let’s get ready to explore the sights and sounds of Middleburg and its surrounding area!

Top U.S. Travel Blogger Alicia Tenise shares her experience at Greenhill Vineyards in Middleburg VA | Top Things to Do in Loudoun County
Top U.S. Travel Blogger Alicia Tenise shares a photo of the Red Fox Inn and Tavern in Middleburg VA | Top Things to Do in Loudoun County

Things to Do in Middleburg, VA | Loudoun County

How To Get To Middleburg, VA | Loudoun County

It is super easy to fly into Loudoun County — fun fact, both of “D.C.’s airports” are located in Virginia. The Dulles International Airport is located right in Loudoun County as well, and it is one of the biggest airports in the area, so there are a plethora of flight options to get to Loudoun County.

If you’re coming from Washington D.C., Loudoun County is approximately an hour away from the Nation’s Capital — give or take some time to account for D.C.’s rush hour traffic. Some toll lanes are available from Tysons Corner to Leesburg, and I love using them for peace of mind. However, you can take a slightly longer route with stoplights if you don’t feel like paying the toll!

How to Get Around Middleburg, VA | Loudoun County

I would drive, rent a car, or hire a private driver if you want to explore Loudoun County. Some parts of Loudoun are a little more rural, making rideshares like Lyft or Uber not as readily available.

If you’re visiting wineries or breweries in the area, I’d highly recommend hiring a private driver for safe transport. I have used Reston Limousine in the past and highly recommend them!

If you’re visiting Loudoun County, there’s a good chance you might be driving on country roads — be careful while driving! It’s manageable but be prepared to put on your high beams at night in some areas.

Zest Boutique in Middleburg VA | Top Things to Do in Loudoun County
The Lucky Knot in Middleburg VA | Top Things to Do in Loudoun County

Chloe's of Middleburg Boutique | Top Things to Do in Loudoun County

Top Things To Do In Middleburg, VA | Loudoun County

Go Shopping in Downtown Middleburg

Downtown Middleburg is jam-packed with historic charm and incredible, locally-owned boutiques. Grab a friend and take a few hours to browse what the local shops have to offer!

Some boutiques that I enjoyed include:

  • Chloe’s of Middleburg: A wonderful BIPOC-owned shop that sells a fun, curated selection of women’s apparel and accessories. The shop owner, Wendy Osborn, is a former buyer for Bergdorf Goodman, and her goal is to bring fresh and dynamic fashion to women of all seasons. I discovered so many new-to-me brands at this boutique, and I can’t wait to visit again the next time I’m in Northern Virginia.
  • The Lucky Knot: If you’re looking for classic, preppy, nautical styles, The Lucky Knot is the perfect shop for you. I loved that they had a great range of price points here, but I was also super excited to see some of my beloved brands, such as Sail to Sable, Scout Bags, and Jack Rogers.
  • Atelier Maison: Designer and tastemaker, Terri Pakravan, curated this home and interior design shop right in Downtown Middleburg, and I was majorly impressed with the selection here. There are so many unique home decor items here, and it’s a great spot to buy one-of-a-kind items for your home or get some design advice. 
  • The Christmas Sleigh: This is a charming Christmas shop my mother, and I have frequented many times. Since this shop is in the D.C. area, you’ll also find some political books that have nothing to do with the holidays, but aside from that, the selection is fantastic!
  • Zest Clothing & Co.: Zest was one of the most affordable shops I visited in Downtown Middleburg, and I loved their selection. They have a lot of budget-friendly, quality brands, and it was on-trend. I can’t wait to return, but I’ll be checking out their social media for new arrivals in the meantime.

Explore Farms & Go On Horse Tours

Loudoun County = horse country. Do yourself a favor and go on a horse tour so that you can explore the great outdoors.

I’m also a big fan of agro-tourism, so visiting local farms would be on my list for my next visit. You can view more info about horse and farm tours in Loudoun County here.

Go to the Spa

There are numerous spas in Loudoun County to enjoy! I took my mom to Salamander Resort’s spa a couple of years ago, and we both loved our experience and cannot wait to return. You can view more spa and wellness options in Loudoun County here.

Tremolo Bar in Historic Middleburg | Top Things to Do in Loudoun County

Harrimans Sunday Brunch | Top Things to Do in Loudoun County
King Street Oyster Bar in Middleburg VA | Top Things to Do in Loudoun County

DInner at the Red Fox Inn and Tavern in Historic Middleburg | Top Things to Do in Loudoun County

Best Restaurants in Middleburg, VA | Loudoun County

Loudoun County is home to so many great eats. Here is a list of my favorite spots to dine in Middleburg, VA, but you can also view more dining options here.


  • Harrimans: I can safely say that this is easily one of the best brunches I’ve ever had in Northern Virginia. Harrimans, located inside the Salamander Resort & Spa, offers a 3-course Sunday Brunch that is bucket-list worthy. This brunch is served family style and is a set menu, but they can accommodate dietary restrictions. The pastries and chicken sausage are made in-house, and Harrimans only uses the freshest ingredients.  

Lunch & Dinner:

  • King Street Oyster Bar: This casual seafood spot serves up some of the best locally sourced seafood in the area. Their oyster selection was impressive, and this Maryland native approves of their crab cakes!
  • Red Fox Inn & Tavern: Everything about this dining experience was divine. The Red Fox Inn & Tavern has a rich history — established in 1728, it is rumored that George Washington was a frequent guest of both the inn and the Tavern. 
    The Tavern offers a four-course dinner experience highlighting unique game and seafood dishes. You can also opt for a local wine pairing that highlights wines from Virginia or the Tavern wine pairing, which features wines from all over the world. I’d recommend going for the Virginia wine pairing so you can get a better idea of what the local wine is all about!
    All in all, this was easily one of the best dining experiences I’ve had in Northern Virginia. The service was impeccable, the food was incredible, and the wine list was an absolute dream.
  • Tremolo Bar: If you’re looking for a great place that offers tapas and a great cocktail list, look no further. Tremolo Bar, located in Downtown Middleburg, is a modern wine bar serving impeccable drinks, premium coffee, and internationally-inspired small plates. I adored the Pan Con Tomate and the New Orleans Shrimp!

Wine Cave Tasting at Boxwood Estate Winery | Top Things to Do in Loudoun County

Barrel Room at Greenhill Vineyards | Top Things to Do in Loudoun County
Walsh Family Wine | Wine Cave Tasting at Boxwood Estate Winery | Top Things to Do in Loudoun County

The Wine Reserve at Waterford | Wine Cave Tasting at Boxwood Estate Winery | Top Things to Do in Loudoun County

Wine Cave Tasting at Boxwood Estate Winery | Top Things to Do in Loudoun County

Best Middleburg, VA | Loudoun County Wineries To Visit

Loudoun County is also known as D.C’s Wine Country®. If you’re looking for wineries to visit in and around Middleburg, here are some of my recommendations:

  • Boxwood Estate Winery: It’s been a few years since I visited this winery, but after revisiting their winery this month, I was very impressed! Boxwood Estate Winery offers award-winning wines and some pretty unique tasting experiences. We opted for the Wine Cave experience, where we could taste in their circular, underground Cave surrounded by French Oak barrels. With this, you do a tasting of six wines, accompanied by their Cheese & Charcuterie board, and concluding with a chocolate + cellar wine pairing. 
  • Cana Vineyards: Cana Vineyards is a delightful boutique winery serving some of Virginia’s best award-winning wines. I love the ambiance here — ample outdoor space to enjoy a glass of wine and views of the rolling hills of Loudoun County. 
  • Greenhill Vineyards: Fun fact — Greenhill Vineyards was the first winery I ever visited when it opened in October 2013. I loved how kind and thoughtful their staff was, and they answered all of my many wine questions back when I was a newbie — and it sparked my love of wine.
    Their Blanc de Blancs has been my favorite for the past decade, but I also adore their red blends!
  • Walsh Family Wine: This winery is in the neighboring town of Purcellville, but it is worth the drive from Middleburg. Walsh Family Wine has the nicest, most incredible staff, and I can confidently say it is one of my favorite wineries in the entire state. Their tasting room is beautifully decorated, and they have a lot of fun with their wines. I’ve visited many times, and the quality has never wavered. 
  • Wine Reserve at Waterford: If I could give an award for the best customer service at a winery, the Wine Reserve at Waterford would easily win this award. Located in the neighboring town of Waterford, VA, they know how to make a memorable tasting experience!
    I visited this winery a few years ago for my birthday, and the attention to detail they had was incredible. A couple of my friends didn’t drink, and they made them the most gorgeous mocktail. I didn’t note the name of my blog at all on my reservation (just came in as a regular customer!), but when I came, they gave us custom menus with my logo printed on it (and yes, I still have that menu until this day)
    This tasting room is also delightful — it has a funky cassette wall, and they also serve their wine flights in test tubes, which is unique. I 100% recommend visiting the Wine Reserve — you will have an incredible time and sample great wines!

Goodstone Inn in Middleburg VA | Top Things to Do in Loudoun County

Goodstone Inn in Middleburg VA | Top Things to Do in Loudoun County
Goodstone Inn in Middleburg VA | Top Things to Do in Loudoun County

Goodstone Inn in Middleburg VA | Top Things to Do in Loudoun County

Where To Stay In Middleburg, VA | Loudoun County

Goodstone Inn and Restaurant is a romantic country inn and award-winning French restaurant set on a breathtaking 265-acre estate in Loudoun County’s wine and horse country.

Enjoy exquisite views of the Blue Ridge Mountains and the countryside from every vantage point. This property features six historic guest houses elegantly decorated in English and French Country decor. 

The Goodstone Inn has 18 luxurious guest rooms on the property, so if you want to make a reservation, do it as quickly as possible — this resort books up quickly! Also, try to make a reservation for their award-winning French restaurant as early as possible. It books up fast, but they offer the finest in farm-to-table gourmet dining with the freshest ingredients from the gardens and farm at Goodstone.

Why You Should Visit Middleburg, VA | Loudoun County

Overall, visiting Middleburg, VA, in Loudoun County is an experience that is an absolute must.

There’s something for everyone, from the breathtaking scenery to the enlightening historical sites to the one-of-a-kind local attractions. Middleburg truly is a gem of a town, offering a range of activities and a welcoming atmosphere. After a visit, you’ll feel as though you have been to the North and the South, a little piece of history and the future all at once.

So, if you’re looking for a fantastic place to visit, Middleburg is your destination! Experience it for yourself and see all the magic this small town offers.

Thank you to Visit Loudoun for sponsoring today’s post! All thoughts and opinions are my own.

Leave a Comment


  1. Christine wrote:

    Thank you for all of the great recs! I need to plan a day trip to Middleburg!

    Posted 5.23.23 Reply