Things to do in Middleburg

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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

It's not difficult to find exciting things to see and do in Middleburg. Learn a little about some local history and check out the top tourist attractions in this charming city. Organize your to-do list now so you're raring to go when you arrive.

Discover the sights of Middleburg with some popular tours & day trips, or get through our list of {10 fun activities in Middleburg fun activities in Middleburg}. We have no booking fees as well as free cancellation, so you can relax and channel your energy into planning an unforgettable vacation.

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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: $55
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Under $25
With kids	Leesburg Premium Outlets Shopping Tour Historic Leesburg Guided Walking Tour

What to do in Middleburg

Free Things to Do in Middleburg

An escape to Middleburg doesn't have to cost a lot. You can leave your wallet at home if you check out:

National Sporting Library & Museum - Take the entire family and set off on a journey of discovery through history with each other.

Things to Do in Middleburg with Kids

You'll find loads of fun things to do with your kids in and around Middleburg. Keep the crew happy with our family friendly experiences.

Looking for sports, concerts, or theater events in Middleburg? Search event tickets to see what's happening today, or to plan what to do this weekend!

Discover the most popular places to visit in Middleburg

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 studying the exhibits at Red Fox Fine Art during your travels in 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

5/5(1 review)

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

3.5/5(3 reviews)

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 trip to Middleburg Historic District.

Chrysalis Vineyards

4/5(2 reviews)

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

Middleburg Community Center

Find out about the history of Middleburg when you take a trip to Middleburg Community Center.

National Sporting Library & Museum

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

Museum of Hounds & Hunting North America

You can spend an afternoon studying the exhibits at Museum of Hounds & Hunting North America during your trip to Middleburg.

Discover the most popular landmarks and neighborhoods in Middleburg

Downtown

While visiting Downtown, you might make a stop by sights like Middleburg Historic District and Red Fox Fine Art.

See our Where To Stay guide

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.

Popular day trips from Middleburg

Leesburg

Upperville

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

Marshall

Frequently asked questions

Is Middleburg worth visiting?

From shopping to outdoor pursuits and history, there are loads of fun things to do in Middleburg. Remember to enjoy the area's mix of unmissable sights, local charm and culture.

How do I spend a day in Middleburg?

National Sporting Library & Museum and The Sporting Gallery are two good places to start your vacation adventures. Remember to explore the dining and shopping options in Middleburg while you're here too.

What is the top tourist attraction in Middleburg?

Don't go home without exploring Greenhill Winery & Vineyards, rated the top tourist attraction in Middleburg.

Is three days enough to stay in Middleburg?

Three days will be plenty of time to check out many city highlights, like Greenhill Winery & Vineyards, Cana Vineyards and Winery and Chrysalis Vineyards. The average stay in Middleburg is two days. If you have the time to extend your escape, Loudoun County isn't far away.

What are some activities to do in Middleburg with kids?

Whether you're traveling with young explorers or playful teenagers, a fun-filled itinerary sets the tone for a great escape. Take a look at our recommendations for what to do in Middleburg with kids.

What to do in Middleburg for adults?

Whether you're an avid foodie, culture enthusiast or fan of nature, there are plenty 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 wanting to enjoy the city without reaching for their wallet. Also, wander around the local neighborhoods and parks, and ask for tips from a local tour guide. It's a simple way to explore the best free things to do in Middleburg.

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Things to do in Loudoun County