Things to do in Middleburg

Activities, attractions and tours

A sunrise over a mountainous landscape with layers of clouds.
A sunset over a snow-covered landscape with bare trees and a clear sky.
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.

Things to do

Leesburg Premium Outlets Shopping Tour

Leesburg Premium Outlets Shopping Tour

RM403
per adult
Leesburg Premium Outlets Shopping Tour
Luxe Day Trip: 3 VA Wineries & Optional Tasting-Inclusive Upgrade

Loudoun County 3-Winery Tour from DC Metro or Leesburg

RM483
per adult
Loudoun County 3-Winery Tour from DC Metro or Leesburg
Guided Thrift Store Walking Tour in Historic Leesburg

Guided Thrift Store Walking Tour in Historic Leesburg

RM201
per adult
Guided Thrift Store Walking Tour in Historic Leesburg
Private Loudoun County Wine Tour from DC with 3 Winery Stops

Private Loudoun County Wine Tour from DC with 3 Winery Stops

RM3,985
per adult
Private Loudoun County Wine Tour from DC with 3 Winery Stops
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What to do in Middleburg

Stay near popular Middleburg attractions

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Glenwood Park

10.0/10 (2 reviews)
Glenwood Park becomes a premier equestrian venue hosting steeplechase races over natural hedges. Bring binoculars to the Virginia Autumn Races in October for the quintessential Middleburg horse racing experience.
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Where to stay in Middleburg

Find the best Middleburg areas for the activities you enjoy most.

Downtown

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

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.