Things to do in Middleburg

Activities, attractions and tours

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.

Browse Middleburg activities by category

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Things to do

Leesburg Premium Outlets Shopping Tour

Leesburg Premium Outlets Shopping Tour

P5,471
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

P7,295
per adult
3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade
Loudoun County Courthouse

Historic Leesburg Guided Walking Tour

P3,344
per adult
Historic Leesburg Guided Walking Tour
Northern Virginia Wine Tours

Northern Virginia Private Custom Wine Tour and Tasting from DC

P60,490
per traveler
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

P60,186
per adult
Private Loudoun County Wine Tour from DC with 3 Winery Stops
Maracas Waterfall

Maracas Waterfall Easiest Hike

P9,119
per adult
Maracas Waterfall Easiest Hike
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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 and neighborhoods for the activities you enjoy most.

Downtown

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

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.