Middleburg, VA

Travel Guide

Middleburg, VA is a beautiful and sweet little town. During the first weekend of December, the town celebrates the holidays with a parade of horses and hounds, ready for the fox hunt; performances from area schools; even more horses; and all the corgis you could ever need. While I was only a visitor, I felt like I was a part of the small town joy and excitement for the holiday. This is certainly something I'll go back to! #virginia #parades #holidays
Middleburg, VA is a beautiful and sweet little town. During the first weekend of December, the town celebrates the holidays with a parade of horses and hounds, ready for the fox hunt; performances from area schools; even more horses; and all the corgis you could ever need. While I was only a visitor, I felt like I was a part of the small town joy and excitement for the holiday. This is certainly something I'll go back to! #virginia #parades #holidays
A quiet town that is one fourth quaint, one fourth stuck in the past, one fourth high society, and one fourth English countryside. Housing less than a thousand residents (as of the 2000 census), Middleburg is a tiny blip of a town with a lot of character. Stroll the streets and look at the old buildings, stop into shops that sell pricy materials, and look at the devotion to horse and hunt. The town was established shortly after the American Revolution and that old-time feel is still there. Plus, fox hunting! I have never been to a place that does fox hunting and the clean, precise clothes can be purchased at local shops.
This winery is fairly new. I think they need a few more years to establish their wine selection. However the wines weren't terrible. I've just had better in this area. But the view from the upper deck is amazing. Definitely worth checking out if you are in the area. Staff is very friendly and knowledgeable. And their sangria was great! #drinkvirginiawine #winesnob #virginia #winery #canavineyard #outdoors
An terrific surprise find on a day of antiquing and vineyard stops. Leaves of Grass is wonderful. A beautiful tasting room in converted barn, great views, and amazing owner hosts. Only 4 wines right now but they are darn good. A long winding driveway right off Rt 50 and a little hard to find so go up driveway at 39060 john mosby (50) hwy. Love this place

Where to stay in Middleburg

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Downtown

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

Downtown
Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street Middleburg VA
Book a stay at this luxury resort in Middleburg. Enjoy free WiFi, an outdoor pool, and a full-service spa. Popular attractions Middleburg Community Center and ...
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Salamander Resort And Spa
The Red Fox Inn & Tavern

The Red Fox Inn & Tavern

4 out of 5
2 E Washington St Middleburg VA
Stay at this inn in Middleburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Red ...
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The Red Fox Inn & Tavern
Hyatt Regency Dulles

Hyatt Regency Dulles

4 out of 5
2300 Dulles Corner Blvd Herndon VA
Book a stay at this golf hotel in Herndon. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean ...
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Hyatt Regency Dulles
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Global Luxury Suites at Reston Town Center

Global Luxury Suites at Reston Town Center

3.5 out of 5
11850 Freedom Drive Reston VA
Book a stay at this business-friendly aparthotel in Reston. Enjoy free WiFi, an outdoor pool, and a 24-hour health club. Popular attractions Reston Town Center ...
Global Luxury Suites at Reston Town Center
Global Luxury Suites at Town Center

Global Luxury Suites at Town Center

4 out of 5
12000 Inspiration St Reston VA
Stay at this apartment in Reston. Enjoy an outdoor pool, a 24-hour front desk, and meeting facilities. Popular attractions Reston Town Center and ArtInsights ...
Global Luxury Suites at Town Center
Global Luxury Suites at Reston

Global Luxury Suites at Reston

4 out of 5
11410 Reston Station Blvd Reston VA
Stay at this apartment in Reston. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Reston Town Center and Fair Oaks Mall are located ...
Global Luxury Suites at Reston
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

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 studying the exhibits at Red Fox Fine Art during your travels in Middleburg. Visit the area's spas, or simply enjoy its restaurants.

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

Glenwood Park

5/5(1 review)

Explore the great outdoors at Glenwood Park, a lovely green space in Middleburg. Visit the area's spas, or simply enjoy its restaurants.

Glenwood Park

Greenhill Winery & Vineyards

3.5/5(3 reviews)

You can enjoy a tasting or tour at Greenhill Winery & Vineyards during your travels to Middleburg. Discover the bars and entertainment venues in this relaxing area.

Greenhill Winery & Vineyards

Middleburg Historic District

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

Middleburg Historic District

Chrysalis Vineyards

4/5(2 reviews)

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

Chrysalis Vineyards

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 savor the top-notch restaurants.

Cana Vineyards and Winery

Things to do

Leesburg Premium Outlets Shopping Tour

Leesburg Premium Outlets Shopping Tour

$90
per adult
Leesburg Premium Outlets Shopping Tour
Loudoun County Courthouse

Historic Leesburg Guided Walking Tour

$55
per adult
Historic Leesburg Guided Walking Tour
Electric Bike Rentals Leesburg, VA: Full Day or Half Day

Electric Bike Rentals Leesburg, VA: Full Day or Half Day

$84
per adult
Electric Bike Rentals Leesburg, VA: Full Day or Half Day
Virginia Wineries Tour

Virginia Wineries Tour

$250
per traveler
Virginia Wineries Tour
Enjoy encounters with the owners and receive a personalized tour from the owner herself.

Virginia Wineries Guided Tour and Tastings from Washington DC

$230
per adult
Virginia Wineries Guided Tour and Tastings from Washington DC
Virginia Winery Excursion by Luxury Vehicle Three wineries

Virginia Winery Excursion by Luxury Vehicle Three wineries

$1,459
per traveler
Virginia Winery Excursion by Luxury Vehicle Three wineries
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Reviews of Middleburg

4.7
Top Destination
5 - Excellent
22
5 - Excellent 73%
4 - Good
7
4 - Good 23%
3 - Okay
1
3 - Okay 3%
2 - Disappointing
0
2 - Disappointing 0%
1 - Terrible
0
1 - Terrible 0%

5/5 - Excellent

Verified traveler

Went there for wineries. Had a wonderful experience.

4/5 - Good

Verified traveler

It's a gorgeous countryside getaway!

5/5 - Excellent

MC

Quant town near a major sites.

3/5 - Okay

Verified traveler

Stores are a little dated

5/5 - Excellent

Verified traveler

Cute town. With good food and unique places to shop! Loved our stay on this town!

5/5 - Excellent

Verified traveler

Centrally located to wineries and breweries in the general surrounding areas.

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