Things to do in Middleburg

Find and book activities, attractions and tours

Photo by Stephanie Sutton
Photo by Stephanie Sutton
Photo by Erica R Hopper
Photo by Erica R Hopper
Photo by Eric Mondres
Photo by Eric Mondres
Photo by Erica R Hopper
Photo by Erica R Hopper

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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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

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

Cana Vineyards and Winery

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

Cana Vineyards and Winery

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.

Greenhill Winery & Vineyards

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.

Glenwood Park

Chrysalis Vineyards

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.

Chrysalis Vineyards

Middleburg Historic District

Find out about the history of Middleburg with a stop at Middleburg Historic District. Visit the area's spas, or simply enjoy its restaurants.

Middleburg Historic District

Tudor Day Spa

You can take time to visit Tudor Day Spa during your travels to Middleburg. Visit the area's spas, or simply enjoy its restaurants.

Tudor Day Spa

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.

National Sporting Library & Museum

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.

Red Fox Fine Art

Middleburg Community Center

Find out about the history of Middleburg when you spend time at Middleburg Community Center. Visit the area's spas, or simply enjoy its restaurants.

Middleburg Community Center

 

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

Leesburg

Purcellville

Purcellville

Photo by danny mccaslin

Bluemont

Photo by mary mahling carns

The Plains

Photo by Erica R Hopper

Aldie

Photo by Alfredo Art Studio

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.