Title: Things to Do in Middleburg in 2026 | Expedia.com [Middleburg Travel Guide](https://expedia.com/Middleburg.dx55837)[Hotels in Middleburg](https://expedia.com/Middleburg-Hotels.d55837.Travel-Guide-Hotels)[Flights to Middleburg](https://expedia.com/Cheap-Flights-To-Middleburg.d55837.Travel-Guide-Flights)[Car Rentals in Middleburg](https://expedia.com/Car-Rentals-In-Middleburg.d55837.Car-Rental-Guide)[Middleburg Vacation Packages](https://expedia.com/Middleburg.d55837.Destination-Travel-Guides) # Things to do in Middleburg ## Find and book activities, attractions and tours ## Visit Middleburg Types of activities Where to stay [Middleburg Travel Guide](https://expedia.com/Middleburg.dx55837) ![central street of the ancient town near Washington. Ancient buildings of shops, hotels and restaurants., strolling tourists.](https://images.trvl-media.com/place/55837/07062b6f-ec03-489a-b962-e9e1809a8973.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![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](https://images.trvl-media.com/place/55837/035eff7a-dec7-4c43-8534-b04184b77b25.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![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.](https://images.trvl-media.com/place/55837/e43a3dbc-c85b-4de0-b62a-a4d0d7e9fb4e.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![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 ](https://images.trvl-media.com/place/55837/df4af456-0ff9-4ee2-9e33-16bd2f6c1a01.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![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 ](https://images.trvl-media.com/place/55837/ea92c1bc-97f5-4931-bccc-26d94f673411.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ### Middleburg Attractions It's not difficult to find exciting things to see and do in Middleburg. Learn a little about some local history and check out the top tourist attractions in this charming city. Organize your to-do list now so you're raring to go when you arrive. Discover the sights of Middleburg with some popular [tours & day trips](https://www.expedia.com/things-to-do/en/search?rid=55837&rfrr=ATG.LP.BodyContent&categories=ToursDayTrips), or get through our list of {9 fun activities in Middleburg [fun activities in Middleburg](https://www.expedia.com/things-to-do/en/search?rid=55837&rfrr=ATG.LP.BodyContent)}. We have no booking fees as well as free cancellation, so you can relax and channel your energy into planning an unforgettable vacation. --- - ![find price illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__find_price.svg) ### Explore activities Explore thousands of experiences from activities and attractions to day tours and transfer. - ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Book with ease Skip the line- book tickets online in minutes to top attractions with free cancellation on many activities. - ![trophy illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Treat yourself One Key members save % or more on select activities, hotels, cars and vacation rentals. [Learn about One Key](https://www.expedia.com/welcome-one-key) --- ## Recommended things to do in Middleburg | Number of things to do | 9 | | ------------------------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------ | | Cheapest thing to do on Expedia | [Historic Leesburg Guided Walking Tour](/things-to-do/historic-leesburg-guided-walking-tour.a3957404.activity-details): $55 | | Top 5 things to do | [Electric Bike Rentals Leesburg, VA: Full Day or Half Day](/things-to-do/electric-bike-rentals-leesburg-va-full-day-or-half-day.a48348068.activity-details)[Leesburg Premium Outlets Shopping Tour](/things-to-do/leesburg-premium-outlets-shopping-tour.a44924891.activity-details)[Historic Leesburg Guided Walking Tour](/things-to-do/historic-leesburg-guided-walking-tour.a3957404.activity-details)[Maracas Waterfall Easiest Hike](/things-to-do/maracas-waterfall-easiest-hike.a50757909.activity-details)[3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade](/things-to-do/vineyard-and-winery-bus-tour-from-metro-dc.a48504181.activity-details) | | Under $25 | | | With kids | [Leesburg Premium Outlets Shopping Tour](/things-to-do/leesburg-premium-outlets-shopping-tour.a44924891.activity-details)[Historic Leesburg Guided Walking Tour](/things-to-do/historic-leesburg-guided-walking-tour.a3957404.activity-details) | ## What to do in Middleburg - For free - With kids ### Free Things to Do in Middleburg An escape to Middleburg doesn't have to cost a lot. You can leave your wallet at home if you check out: **National Sporting Library & Museum** \- Take the entire family and set off on a journey of discovery through history with each other. ### Things to Do in Middleburg with Kids You'll find loads of fun things to do with your kids in and around Middleburg. Keep the crew happy with our [family friendly experiences](https://www.expedia.com/things-to-do/en/search?rid=55837&rfrr=ATG.LP.BodyContent&categories=Family%20Friendly). --- Looking for sports, concerts, or theater events in Middleburg? [Search event tickets](https://www.expedia.com/event-tickets/) to see what's happening today, or to plan what to do this weekend! --- --- ### Discover the most popular places to visit in Middleburg ![Tranquil Glenwood Pond landscape with water dam, green forest hill, and white summer cloudscape in Prince Edward Island, Canada](https://images.trvl-media.com/place/553248621532661869/c3ccace8-4825-4634-986a-be1dcd14cb71.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Glenwood-Park-Middleburg.d553248621532661869.Vacation-Attraction) ![Red fox in winter, Japan. Red Fox in winter landscape. Japanese winter landscape with the animal.](https://images.trvl-media.com/place/553248621532661874/ca8e16e6-f8da-4ef0-926a-3cb5c9c97ab8.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Red-Fox-Fine-Art-Downtown.d553248621532661874.Vacation-Attraction) #### 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. [](https://expedia.com/Greenhill-Winery-Vineyards-Middleburg.d553248621532661879.Vacation-Attraction) #### Middleburg Historic District You can learn about the history of Middleburg with a trip to Middleburg Historic District. [](https://expedia.com/Middleburg-Historic-District-Middleburg.d950929389447987200.Vacation-Attraction) #### 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. [](https://expedia.com/Cana-Vineyards-And-Winery-Middleburg.d553248621532661900.Vacation-Attraction) #### 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. [](https://expedia.com/Chrysalis-Vineyards-Middleburg.d553248621532661899.Vacation-Attraction) #### 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. [](https://expedia.com/Tudor-Day-Spa-Downtown.d553248621532661871.Vacation-Attraction) #### Middleburg Community Center Find out about the history of Middleburg when you take a trip to Middleburg Community Center. [](https://expedia.com/Middleburg-Community-Center-Middleburg.d950929376688914432.Vacation-Attraction) #### National Sporting Library & Museum You can spend an afternoon exploring the galleries in National Sporting Library & Museum during your travels in Middleburg. Visit the area's spas, or simply enjoy its restaurants. [](https://expedia.com/National-Sporting-Library-Museum-Middleburg.d553248621532661872.Vacation-Attraction) ### Discover the most popular landmarks and neighborhoods in Middleburg ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown While visiting Downtown, you might make a stop by sights like Middleburg Historic District and Red Fox Fine Art. [](https://expedia.com/Middleburg-Downtown.dx986019551221510144) [See our Where To Stay guide](https://expedia.com/Middleburg.dx55837.Where-To-Stay?rfrr=TG.LP..Neighborhoods) --- Looking for fun things to do nearby? Check [things to do near me](https://www.expedia.com/things-to-do-near-me) to find and book the best things to do, fun activities, and top attractions wherever you happen to be. --- ## Popular day trips from Middleburg ![Rows of wine grapes plants on vineyards of Virginia in the suburbs of Leesburg. Wine farm and agricultural machinery. Drone view.](https://images.trvl-media.com/place/8575/679d9a34-9770-46a5-9174-6277726505b7.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Leesburg ![Welcome sign to Upperville Virginia in Fauquier County.](https://images.trvl-media.com/place/184116/deb8a32e-602b-43b9-802d-e775f9221444.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Upperville ![Purcellville Town Hall, 221 South Nursery Avenue, Purcellville, Virginia](https://images.trvl-media.com/place/6338641/8aadf7b5-77e7-4f4e-ac26-036b98787026.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Purcellville ![Vineyard views at Bluemont Vineyard in northern Virginia.](https://images.trvl-media.com/place/6348602/d281e8a7-03d8-4064-8cbf-609c62d2fa45.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Bluemont ![Scenic views along virginia creeper trail](https://images.trvl-media.com/place/3000460647/41631fe1-839c-4608-a872-ed7cb99f0db4.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Round Hill ![Great coffee shop in the Plains. Also has a bike shop inside. Everything here is also gluten free, including soups, sandwiches, etc.](https://images.trvl-media.com/place/3000460694/146bbf6a-ccb3-4abc-9848-1f7571f83712.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### The Plains ![There's nothing better than taking drives in the fall. I love all autumnal things and spotting beautiful driveways with rich colors such as this is worth pulling over and taking a few pictures. I'm jealous of whoever lives here.](https://images.trvl-media.com/place/553248622877094266/18608b2e-1119-4905-8632-20967f9a86c7.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Aldie ![View of the Blue Ridge Mountains from South Marshall, in Shenand](https://images.trvl-media.com/place/553248633272644103/9c26efb4-7627-4a4e-a696-187c1b8e0f98.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Marshall ## Frequently asked questions ### Is Middleburg worth visiting? ### How do I spend a day in Middleburg? ### What is the top tourist attraction in Middleburg? ### Is three days enough to stay in Middleburg? ### What are some activities to do in Middleburg with kids? > - [Leesburg Premium Outlets Shopping Tour](https://expedia.com/things-to-do/leesburg-premium-outlets-shopping-tour.a44924891.activity-details) > - [Historic Leesburg Guided Walking Tour](https://expedia.com/things-to-do/historic-leesburg-guided-walking-tour.a3957404.activity-details) ### What to do in Middleburg for adults? ### Are there free things to do in Middleburg? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Hotels near The Byrne Gallery ](https://www.expedia.com/The-Byrne-Gallery-Hotels.0-l553248621532661875-0.Travel-Guide-Filter-Hotels) - [Hotels near Tudor Day Spa ](https://www.expedia.com/Tudor-Day-Spa-Hotels.0-l553248621532661871-0.Travel-Guide-Filter-Hotels) - [Hotels near National Sporting Library & Museum ](https://www.expedia.com/National-Sporting-Library-Museum-Hotels.0-l553248621532661872-0.Travel-Guide-Filter-Hotels) - [Hotels near The Boxwood Winery ](https://www.expedia.com/The-Boxwood-Winery-Hotels.0-l553248621532661867-0.Travel-Guide-Filter-Hotels) - [Hotels near Greenhill Winery & Vineyards ](https://www.expedia.com/Greenhill-Winery-Vineyards-Hotels.0-l553248621532661879-0.Travel-Guide-Filter-Hotels) - [Hotels near Glenwood Park ](https://www.expedia.com/Glenwood-Park-Hotels.0-l553248621532661869-0.Travel-Guide-Filter-Hotels) - [Hotels near Chrysalis Vineyards ](https://www.expedia.com/Chrysalis-Vineyards-Hotels.0-l553248621532661899-0.Travel-Guide-Filter-Hotels) - 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[Cabin Rentals in Upperville ](https://www.expedia.com/Upperville-Cabins.d184116-aaCabins.Travel-Guide-Accommodation) - [5 Star Hotels in Upperville ](https://www.expedia.com/5Star-Upperville-Hotels.s50-0-d184116.Travel-Guide-Filter-Hotels) - [Motels in Upperville ](https://www.expedia.com/Upperville-Motels.d184116-aaMotels.Travel-Guide-Accommodation) - [Lenah Hotels ](https://www.expedia.com/Lenah-Hotels.d553248635975876363.Travel-Guide-Hotels) - [Hotels near Stone Tower Winery ](https://www.expedia.com/Stone-Tower-Winery-Hotels.0-l553248633992315417-0.Travel-Guide-Filter-Hotels) - [Hotels near Winery at La Grange ](https://www.expedia.com/Winery-At-La-Grange-Hotels.0-l6163075-0.Travel-Guide-Filter-Hotels) - [Hotels near Evergreen Mills Equestrian and Hiking Trail ](https://www.expedia.com/Evergreen-Mills-Equestrian-And-Hiking-Trail-Hotels.0-l553248621532661973-0.Travel-Guide-Filter-Hotels) - [Marshall Hotels ](https://www.expedia.com/Marshall-Hotels.d553248633272644103.Travel-Guide-Hotels) - [Flights to Aldie ](https://www.expedia.com/Cheap-Flights-To-Aldie.d553248622877094266.Travel-Guide-Flights) - [Flights from Aldie ](https://www.expedia.com/lp/flights/553248622877094266/flights-from-aldie) - [Flights to Blue Ridge ](https://www.expedia.com/Cheap-Flights-To-Blue-Ridge.d553248635976006713.Travel-Guide-Flights) - [Flights from Blue Ridge ](https://www.expedia.com/lp/flights/553248635976006713/flights-from-blue-ridge) - [Flights to The Plains ](https://www.expedia.com/Cheap-Flights-To-The-Plains.d3000460694.Travel-Guide-Flights) - [Flights to Upperville ](https://www.expedia.com/Cheap-Flights-To-Upperville.d184116.Travel-Guide-Flights) - [Flights to Marshall ](https://www.expedia.com/Cheap-Flights-To-Marshall.d553248633272644103.Travel-Guide-Flights) - [The Byrne Gallery ](https://www.expedia.com/The-Byrne-Gallery-Middleburg.d553248621532661875.Vacation-Attraction) - [Red Fox Fine Art ](https://www.expedia.com/Red-Fox-Fine-Art-Middleburg.d553248621532661874.Vacation-Attraction) - [Tudor Day Spa ](https://www.expedia.com/Tudor-Day-Spa-Middleburg.d553248621532661871.Vacation-Attraction) - [National Sporting Library & Museum ](https://www.expedia.com/National-Sporting-Library-Museum-Middleburg.d553248621532661872.Vacation-Attraction) - [The Boxwood Winery ](https://www.expedia.com/The-Boxwood-Winery-The-Plains.d553248621532661867.Vacation-Attraction) - [Greenhill Winery & Vineyards ](https://www.expedia.com/Greenhill-Winery-Vineyards-Middleburg.d553248621532661879.Vacation-Attraction) - [Glenwood Park ](https://www.expedia.com/Glenwood-Park-Middleburg.d553248621532661869.Vacation-Attraction) - [Cana Vineyards and Winery ](https://www.expedia.com/Cana-Vineyards-And-Winery-Middleburg.d553248621532661900.Vacation-Attraction) - [Visit Aldie ](https://www.expedia.com/Aldie.dx553248622877094266) - [Aldie Vacations ](https://www.expedia.com/Aldie.d553248622877094266.Destination-Travel-Guides) - [Aldie Mill Historic Park ](https://www.expedia.com/Aldie-Mill-Historic-Park-Aldie.d553248621532661902.Vacation-Attraction) - [Visit Philomont ](https://www.expedia.com/Philomont.dx3000460608) - [Quattro Goomba's Winery ](https://www.expedia.com/Quattro-Goombas-Winery-Aldie.d553248621532661904.Vacation-Attraction) - [Oak Hill Plantation ](https://www.expedia.com/Oak-Hill-Plantation-Aldie.d6093219.Vacation-Attraction) - [Visit Rectortown ](https://www.expedia.com/Rectortown.dx3000355260) - [Visit The Plains ](https://www.expedia.com/The-Plains.dx3000460694) - [Oatlands Historic House & Gardens ](https://www.expedia.com/Oatlands-Historic-House-Gardens-Leesburg.d553248621533116510.Vacation-Attraction) - [Loudoun Museum ](https://www.expedia.com/Loudoun-Museum-Leesburg.d553248621533116509.Vacation-Attraction) - [Morven Park ](https://www.expedia.com/Morven-Park-Leesburg.d553248621533116511.Vacation-Attraction) - [Oatlands Historic House and Gardens ](https://www.expedia.com/Oatlands-Historic-House-And-Gardens-Leesburg.d6221542.Vacation-Attraction) - [Visit Upperville ](https://www.expedia.com/Upperville.dx184116) - 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