What to do in Middleburg, VA

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Middleburg travel guide

central street of the ancient town near Washington. Ancient buildings of shops, hotels and restaurants., strolling tourists.

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What to do in Middleburg

Popular places to visit

Tranquil Glenwood Pond landscape with water dam, green forest hill, and white summer cloudscape in Prince Edward Island, Canada

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.

Red fox in winter, Japan. Red Fox in winter landscape. Japanese winter landscape with the animal.

Red Fox Fine Art

You can spend an afternoon browsing the exhibits at Red Fox Fine Art during your trip to Middleburg. Visit the area's spas or simply enjoy its restaurants.

Middleburg Historic District

You can learn about the history of Middleburg with a visit to Middleburg Historic District.

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 trendy area.

Chrysalis Vineyards

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

Cana Vineyards and Winery

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

Middleburg Community Center

Find out about the history of Middleburg when you spend time at Middleburg Community Center.

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.

Museum of Hounds & Hunting North America

You can spend an afternoon exploring the galleries in Museum of Hounds & Hunting North America during your travels in Middleburg.

Explore areas of Middleburg

Downtown

If you're spending some time in Downtown, Middleburg Historic District and Museum of Hounds & Hunting North America 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.