Things to do in Middleburg

Activities, attractions and tours

Autumn morning mist shrouds the Shenandoah Mountains in the Blue Ridge Mountains of Virginia.
Winter sunrise over the Blue Ridge Mountains of Virginia in the Shenandoah Valley
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.

Browse Middleburg activities by category

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Things to do

Guided Thrift Store Walking Tour in Historic Leesburg

Guided Thrift Store Walking Tour in Historic Leesburg

HK$2,352
per traveller
Guided Thrift Store Walking Tour in Historic Leesburg
Leesburg Premium Outlets Shopping Tour

Leesburg Premium Outlets Shopping Tour

HK$784
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

HK$941
per adult
3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade
Northern Virginia Wine Tours

Northern Virginia Private Custom Wine Tour and Tasting from DC

HK$7,804
per traveller
80% of travellers recommend
Northern Virginia Private Custom Wine Tour and Tasting from DC
Private Loudoun County Wine Tour from DC with 3 Winery Stops

Private Loudoun County Wine Tour from DC with 3 Winery Stops

HK$7,765
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

A red fox standing in the snow.

Red Fox Fine Art

9.6/10 (10 reviews)
America's leading gallery for sporting art, Red Fox Fine Art showcases exquisite 19th and 20th-century paintings and sculptures. Browse the curated collection that celebrates equestrian heritage in an intimate setting.
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Where to stay in Middleburg

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

Downtown

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

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

Leesburg

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.