Title: 10 TOP Things to Do in Middleburg September 2025 | Expedia.ca [Hotels in Middleburg](https://expedia.ca/Middleburg-Hotels.d55837.Travel-Guide-Hotels)[Middleburg Car Rentals](https://expedia.ca/Car-Rentals-In-Middleburg.d55837.Car-Rental-Guide)[Middleburg Vacation Packages](https://expedia.ca/Middleburg.d55837.Destination-Travel-Guides) # What to do in Middleburg, VA ## Activities, attractions and tours ## Visit Middleburg Types of activities [Middleburg travel guide](https://expedia.ca/Middleburg.dx55837) ![Photo by Stephanie Sutton](https://mediaim.expedia.com/destination/2/993632cc8e31932137f542011e4b02a8.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Stephanie Sutton](https://mediaim.expedia.com/destination/2/993632cc8e31932137f542011e4b02a8.jpg) ![Photo by Erica R Hopper](https://mediaim.expedia.com/destination/2/1860de1dc0427173d326e908a595245f.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Erica R Hopper](https://mediaim.expedia.com/destination/2/1860de1dc0427173d326e908a595245f.jpg) ![Photo by Eric Mondres](https://mediaim.expedia.com/destination/2/c9573d0b783231a056d1a18ca81699ce.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Eric Mondres](https://mediaim.expedia.com/destination/2/c9573d0b783231a056d1a18ca81699ce.jpg) ![Photo by Erica R Hopper](https://mediaim.expedia.com/destination/2/6b4728a35f8031e7cbfd72811e997596.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Erica R Hopper](https://mediaim.expedia.com/destination/2/6b4728a35f8031e7cbfd72811e997596.jpg) ## Middleburg Attractions Let Expedia help you experience the best that Middleburg has to offer! If you’re looking for fun itinerary ideas, we can provide you with a list of the top sightseeing attractions, as well as helping you to find unmissable activities. Whether you’re travelling with your family, planning a romantic trip with your loved one, or visiting on business, we’ll make it easy to plan an unforgettable holiday that checks all the boxes. #### Activities and Tours Middleburg is crammed with must-see places to visit and things to do. We can help you decide where to stay, and make it a breeze to explore the surrounding areas with our guides on where to go, what to see and when to see it. No matter how long your stay, it’s easy to find places of interest in Middleburg to make sure that you enjoy your experience to the fullest and don’t miss a thing. Leave the local knowledge to us and leave the hassle behind. If you’re planning a visit, why not check out our handy guides to places of interest in the area? You can browse lists of things to do, learn about the most popular attractions, and get help with planning the details of your trip. Expedia makes it easy for you to check out all the top sights. #### Middleburg Attractions Expedia has something for everyone, so whether you’re planning to get active on a summer holiday, put a spring in your step with a romantic rendezvous, or pamper yourself with a leisurely winter trip, you’ll find plenty of attractions to keep you entertained. In addition to scheduling local tours, booking reservations and scoring advance event tickets, Expedia makes it easy to book your flight, hotel and rental car in advance, all on one consolidated travel itinerary, making for hassle-free travel and freeing you up to explore the sights of Middleburg. Looking for things to do can be time consuming, but we can take the hassle out of planning your holiday. Whether you’re looking to get active in the great outdoors, sample the cuisine or catch up with the vibrant local culture, our guides to Middleburg attractions ensure that you’ll have a successful trip, whatever the season. * * * Explore thousands of activities with **free cancellation and no added fees**. Design your experience with airport transfers, excursions, day tours & more. Get an insider's look in what to book before you travel. * * * ## Recommended things to do in Middleburg | Number of things to do | 10 | | --- | --- | | Cheapest thing to do on Expedia | [Historic Leesburg Guided Walking Tour](https://expedia.ca/things-to-do/historic-leesburg-private-walking-tour.a3957404.activity-details): CA $76 | | Top 5 things to do | - [Mosaic Lamp Workshop](https://expedia.ca/things-to-do/mosaic-lamp-workshop.a49322848.activity-details) - [Vineyard and Winery Bus Tour from Metro DC](https://expedia.ca/things-to-do/vineyard-and-winery-bus-tour-from-metro-dc.a48504181.activity-details) - [Historic Leesburg Guided Walking Tour](https://expedia.ca/things-to-do/historic-leesburg-private-walking-tour.a3957404.activity-details) - [Electric Bike Rentals Leesburg, VA: Full Day or Half Day](https://expedia.ca/things-to-do/electric-bike-rentals-leesburg-va-full-day-or-half-day.a48348068.activity-details) - [Rug Tufting Workshop](https://expedia.ca/things-to-do/rug-tufting-workshop.a49323004.activity-details) | | Half-day tours | - [Mosaic Lamp Workshop](https://expedia.ca/things-to-do/mosaic-lamp-workshop.a49322848.activity-details) - [Historic Leesburg Guided Walking Tour](https://expedia.ca/things-to-do/historic-leesburg-private-walking-tour.a3957404.activity-details) - [Rug Tufting Workshop](https://expedia.ca/things-to-do/rug-tufting-workshop.a49323004.activity-details) | | With kids | - [Mosaic Lamp Workshop](https://expedia.ca/things-to-do/mosaic-lamp-workshop.a49322848.activity-details) - [Historic Leesburg Guided Walking Tour](https://expedia.ca/things-to-do/historic-leesburg-private-walking-tour.a3957404.activity-details) - [Rug Tufting Workshop](https://expedia.ca/things-to-do/rug-tufting-workshop.a49323004.activity-details) - [Leesburg Premium Outlets Shopping Tour](https://expedia.ca/things-to-do/leesburg-premium-outlets-shopping-tour.a44924891.activity-details) | ## What to do in Middleburg * * * ### Discover the most popular places to visit in Middleburg ![Cana Vineyards and Winery](https://mediaim.expedia.com/destination/2/993632cc8e31932137f542011e4b02a8.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Cana Vineyards and Winery You can enjoy a tasting or tour at Cana Vineyards and Winery during your travels to Middleburg. While in this trendy area, you can savor the top-notch restaurants. [](https://expedia.ca/Cana-Vineyards-And-Winery-Middleburg.d553248621532661900.Vacation-Attraction) #### 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. [](https://expedia.ca/Greenhill-Winery-Vineyards-Middleburg.d553248621532661879.Vacation-Attraction) #### 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. [](https://expedia.ca/Glenwood-Park-Middleburg.d553248621532661869.Vacation-Attraction) #### Chrysalis Vineyards 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.ca/Chrysalis-Vineyards-Middleburg.d553248621532661899.Vacation-Attraction) #### Middleburg Historic District Find out about the history of Middleburg with a stop at Middleburg Historic District. Visit the area's spas, or simply enjoy its restaurants. [](https://expedia.ca/Middleburg-Historic-District-Middleburg.d950929389447987200.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.ca/Tudor-Day-Spa-Middleburg.d553248621532661871.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.ca/National-Sporting-Library-Museum-Middleburg.d553248621532661872.Vacation-Attraction) #### 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.ca/Red-Fox-Fine-Art-Middleburg.d553248621532661874.Vacation-Attraction) #### Middleburg Community Center Find out about the history of Middleburg when you spend time at Middleburg Community Center. Visit the area's spas, or simply enjoy its restaurants. [](https://expedia.ca/Middleburg-Community-Center-Middleburg.d950929376688914432.Vacation-Attraction) * * * Looking for fun things to do nearby? Check [things to do near me](https://www.expedia.ca/things-to-do-near-me) to find and book the best things to do, fun activities, and top attractions wherever you happen to be. * * * ## 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. > > > > - [Mosaic Lamp Workshop](https://expedia.ca/things-to-do/mosaic-lamp-workshop.a49322848.activity-details) > - [Historic Leesburg Guided Walking Tour](https://expedia.ca/things-to-do/historic-leesburg-private-walking-tour.a3957404.activity-details) > - [Rug Tufting Workshop](https://expedia.ca/things-to-do/rug-tufting-workshop.a49323004.activity-details) > - [Leesburg Premium Outlets Shopping Tour](https://expedia.ca/things-to-do/leesburg-premium-outlets-shopping-tour.a44924891.activity-details) ### 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. 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