Things to do in Middleburg

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A street with parked cars and storefronts, including a jewelry store and a restaurant.
A group of dogs standing on grass, with a horse in the background.
A group of hounds on a grassy field with a horse and rider in the foreground.
A horse and rider on a paved path with a group of dogs following.
A horse-drawn carriage in a town square with autumn trees and historic buildings in the background.

Things to do

Leesburg Premium Outlets Shopping Tour

Leesburg Premium Outlets Shopping Tour

￥14,396
per adult
Leesburg Premium Outlets Shopping Tour
Luxe Day Trip: 3 VA Wineries & Optional Tasting-Inclusive Upgrade

3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade

￥19,192
per adult
3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade
Private Loudoun County Wine Tour from DC with 3 Winery Stops

Private Loudoun County Wine Tour from DC with 3 Winery Stops

￥158,351
per adult
Private Loudoun County Wine Tour from DC with 3 Winery Stops
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What to do in Middleburg

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Glenwood Park

10.0/5 (2 reviews)
Glenwood Park becomes a premier equestrian venue hosting steeplechase races over natural hedges. Bring binoculars to the Virginia Fall Races in October for the quintessential Middleburg horse racing experience.
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Where to stay in Middleburg

Find the best Middleburg areas and neighborhoods for the activities you enjoy most. Learn more about Middleburg
Learn more about Middleburg

Downtown

While visiting Downtown, you might make a stop by sights like Middleburg Historic District and Middleburg Community Center.

Popular day trips from Middleburg

A calm lake surrounded by dense trees and a clear sky.

Leesburg

A river valley with dense foliage, a prominent rock formation, and a clear blue sky.

Purcellville

A vineyard with rows of grapevines, a winding road, and a distant view of rolling hills and a cloudy sky.

Bluemont

A park path with autumn leaves, trees, and a fence.

Aldie

A mountainous landscape with dense green forests and a clear blue sky with fluffy clouds.

Marshall

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 vacationing 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 neighborhoods, 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.