What to do in Middleburg, VA

Activities, attractions and tours

Visit Middleburg

Types of activities

Where to stay

Middleburg travel guide

Middleburg, VA is a beautiful and sweet little town. During the first weekend of December, the town celebrates the holidays with a parade of horses and hounds, ready for the fox hunt; performances from area schools; even more horses; and all the corgis you could ever need. While I was only a visitor, I felt like I was a part of the small town joy and excitement for the holiday. This is certainly something I'll go back to!
#virginia #parades #holidays

A quiet town that is one fourth quaint, one fourth stuck in the past, one fourth high society, and one fourth English countryside. Housing less than a thousand residents (as of the 2000 census), Middleburg is a tiny blip of a town with a lot of character. Stroll the streets and look at the old buildings, stop into shops that sell pricy materials, and look at the devotion to horse and hunt. The town was established shortly after the American Revolution and that old-time feel is still there. Plus, fox hunting! I have never been to a place that does fox hunting and the clean, precise clothes can be purchased at local shops.

This winery is fairly new. I think they need a few more years to establish their wine selection. However the wines weren't terrible. I've just had better in this area. But the view from the upper deck is amazing. Definitely worth checking out if you are in the area. Staff is very friendly and knowledgeable. And their sangria was great! #drinkvirginiawine
#winesnob #virginia
#winery #canavineyard
#outdoors

An terrific surprise find on a day of antiquing and vineyard stops. Leaves of Grass is wonderful. A beautiful tasting room in converted barn, great views, and amazing owner hosts. Only 4 wines right now but they are darn good. A long winding driveway right off Rt 50 and a little hard to find so go up driveway at 39060 john mosby (50) hwy. Love this place

Middleburg Attractions

Let Expedia help you to experience the best that Middleburg has to offer! If you’re planning a trip to Middleburg, we can provide you with a list of the top sightseeing attractions, as well as helping you to find unmissable activities. Whether you’re travelling to Middleburg with your family, planning a romantic trip with your loved one, or visiting on business, we’ll make it easy to plan an unforgettable holiday that checks all the boxes.

Places of interest in Middleburg

Middleburg is crammed with must-see places to visit and things to do. We can help you decide where to stay in Middleburg, and make it a breeze to explore Middleburg and the surrounding areas with our guides on where to go, what to see and when to see it. No matter how long your stay, it’s easy to find places of interest in Middleburg to make sure that you enjoy your holiday to the fullest and don’t miss a thing. Leave the local knowledge to us and leave the hassle behind.

If you’re planning a visit to Middleburg, why not check out our handy guides to places of interest in the area? You can browse lists of things to do, learn about the most popular attractions, and get help with planning the details of your trip. Expedia makes it easy for you to check out all the top sights in Middleburg.

Middleburg attractions

Middleburg has something for everyone, so whether you’re planning to get active on a summer holiday, put a spring in your step with a romantic rendezvous, or pamper yourself with a leisurely winter trip, you’ll find plenty of attractions in Middleburg to keep you entertained. Expedia makes it easy to book your flight, hotel and rental car in advance, making for hassle-free travel and freeing you up to explore the sights of Middleburg.

Looking for things to do in Middleburg can be time-consuming, but we can take the hassle out of planning your holiday. Whether you’re looking to get active in the great outdoors, sample the cuisine of Middleburg or catch up with the vibrant local culture, our guides to Middleburg attractions ensure that you’ll have a successful trip, whatever the season. Happy trails!

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Recommended things to do in Middleburg

Number of things to do	10
Cheapest thing to do on Expedia	Historic Leesburg Guided Walking Tour: £41
Top 5 things to do	Electric Bike Rentals Leesburg, VA: Full Day or Half Day Leesburg Premium Outlets Shopping Tour Maracas Waterfall Vineyard and Winery Bus Tour from Metro DC Historic Leesburg Guided Walking Tour
Half-day tours	Maracas Waterfall Historic Leesburg Guided Walking Tour
With kids	Leesburg Premium Outlets Shopping Tour Historic Leesburg Guided Walking Tour

What to do in Middleburg

Popular places to visit

Red fox in winter, Japan. Red Fox in winter landscape. Japanese winter landscape with the animal.

Red Fox Fine Art

You can spend an afternoon browsing the exhibits at Red Fox Fine Art during your trip to Middleburg. Visit the area's spas or simply enjoy its restaurants.

Tranquil Glenwood Pond landscape with water dam, green forest hill, and white summer cloudscape in Prince Edward Island, Canada

Glenwood Park

Explore the great outdoors at Glenwood Park, a lovely green space in Middleburg. Visit the area's spas or simply enjoy its restaurants.

Greenhill Winery & Vineyards

You can enjoy a tasting or tour at Greenhill Winery & Vineyards during your travels to Middleburg. Discover the bars and entertainment venues in this relaxing area.

Middleburg Historic District

You can learn about the history of Middleburg with a visit to Middleburg Historic District.

Chrysalis Vineyards

You can enjoy a tasting or tour at Chrysalis Vineyards during your travels to Middleburg. While in this trendy area, you can savour the top-notch restaurants.

Cana Vineyards and Winery

You can enjoy a tasting or tour at Cana Vineyards and Winery during your travels to Dover. While in this trendy area, you can savour the top-notch restaurants.

The Byrne Gallery

You can spend an afternoon studying the exhibits at The Byrne Gallery during your trip to Middleburg. Visit the area's spas or simply enjoy its restaurants.

National Sporting Library & Museum

You can spend an afternoon exploring the galleries in National Sporting Library & Museum in Middleburg. Visit the area's spas or simply enjoy its restaurants.

Middleburg Community Center

Find out about the history of Middleburg when you spend time at Middleburg Community Center.

Explore areas of Middleburg

Downtown

If you're spending some time in Downtown, Middleburg Historic District and Red Fox Fine Art are top sights worth seeing.

Looking for fun things to do nearby? Check things to do near me to find and book the best things to do, fun activities, and top attractions wherever you happen to be.

Day trip destinations from Middleburg

Purcellville

Bluemont

Scenic views along virginia creeper trail

Round Hill

The Plains

There's nothing better than taking drives in the fall. I love all autumnal things and spotting beautiful driveways with rich colors such as this is worth pulling over and taking a few pictures. I'm jealous of whoever lives here.

Aldie

Frequently asked questions

Is Middleburg worth visiting?

Whether you're coming to discover the local charm and cultural hotspots or sample regional foods and explore in nature, there are many things to do in Middleburg.

How do I spend a day in Middleburg?

National Sporting Library & Museum and The Sporting Gallery are two awesome places to start your getaway adventures. Remember to check out the dining and retail options in Middleburg while you're here too.

What is the top tourist attraction in Middleburg?

The top tourist attraction in Middleburg is Greenhill Winery & Vineyards, so be sure to include it on your sightseeing list.

Is three days enough to stay in Middleburg?

Three days in Middleburg is enough to visit the city's main attractions. Many guests spend two days on average. Greenhill Winery & Vineyards, Cana Vineyards and Winery and Chrysalis Vineyards are among the top-rated sights. Want to experience more? Hang around a while longer to explore nearby hotspots like Loudoun County.

What are some activities to do in Middleburg with kids?

Deciding what to do in Middleburg with kids has never been simpler. Whether you're holidaying with teenagers or toddlers, there are loads of family-friendly sights to keep everyone entertained here.

What to do in Middleburg for adults?

Whether you're an avid foodie, culture enthusiast or outdoor explorer, there are loads of things to do in Middleburg for adults including Greenhill Winery & Vineyards and Quattro Goomba's Winery.

Are there free things to do in Middleburg?

In Middleburg, National Sporting Library & Museum is a top spot for anyone planning to tour the city without reaching for their wallet. Also, wander around the parks and other neighbourhoods, and ask for recommendations from a local tour guide. It's an easy way to learn about the best free things to do in Middleburg.