23 Best & Fun Things to Do in Middleburg (VA)

In search of the best and fun things to do in Middleburg, VA?

Middleburg is a beautiful town in Loudoun County, in the state of Virginia, United States. It is one of the smallest towns, with a population of 669 in 2021.

Found just 40 minutes from Washington, Middleburg is commonly referred to as the horse and hunt capital of the nation due to the town’s foxhunting, large estates, and steeplechases.

Middleburg is undisputedly a simple but elegant American small city. It is home to unique boutiques, historical landmarks, art galleries, and restaurants.

The town was founded by John Leven Powell, a Virginia statesman and an American Revolutionary Lieutenant.

The best places to visit in Middleburg, VA, include 50 West Vineyards, the Red Fox Inn and Tavern, the Middleburg Antique Gallery, Middleburg Common Grounds, the National Sporting Library and Museum, the Boxwood Estate Winery, and more.

Check out the top things to do in Middleburg, VA.

Things to Do in Middleburg, VA

1. The Red Fox Inn and Tavern

Red Fox Inn and Tavern
Credits: lcm1863 / Flickr
Red Fox Inn and Tavern

Existed for almost three centuries, the Red Fox Inn and Tavern is a classic boutique inn and tavern founded in 1728.

The Red Fox Inn and Tavern offer a blend of a classy and romantic atmosphere, being found not too far from Wine Country and Virginia.

The inn features beautiful and comfortable rooms designed in southern style, offering a whole new culinary experience.

It features a rustic tavern offering selection of gourmet meals such as Prime filet mignon, butternut squash wontons, and New York strip steaks.

The Red Fox Inn and Tavern feature the Night Fox Pub, which offers Clever pub fare, including burgers, lamb sausage, mac and cheese, etc.

Address: 2 E Washington St, Middleburg, VA 20117, United States

2. Salamander Tree Top Zip Tour

Salamander Tree Top Zip Tour
Credits: Thanchanok.p / Shutterstock

Among the fun things to do in Middleburg, VA, is to go zip-lining at the Salamander Tree Top Zip Tour, one of the latest adventure attractions in the region.

Salamander Tree Top Zip Tour offers different fun packages, such as a rappelling adventure, a 20-acre zip-lining adventure, a leadership odyssey, and survival 101.

Empower Adventures houses the Salamander Tree Top Zip Tour as a family-friendly destination located at Salamander Resort.

The area features eight stations, two sky bridges, and five zip lines with Empower guides enlightening the public about the various flora and fauna scattered throughout the preserve region.

Salamander Tree Top Zip Tour is strategically located, making it easy to spot and perfect for many families.

Address: 500 N Pendleton St Middleburg, VA 20117 United States

3. The Sporting Gallery

If you want to learn about the city’s sporting history, add a visit to the Sporting Gallery to your list of top things to do in Middleburg, VA.

The Sporting Gallery is one of the oldest art galleries in the United States, which features wildlife and sporting-related artworks.

The Gallery celebrates the rich history of Middleburg, basically on sporting and foxhunting. It is found in an elegant notable Duffy House erected in 1820, located in the town’s downtown area.

Many famous artists are on display, such as Peter Sculthorpe and Linda Volrath, who are reputable for their unique animal paintings.

You will find an extensive collection of Fox porcelains, such as Royal Doulton pieces, Nymphenburg, and Royal Worcester.

The Sporting Gallery showcases a unique collection of animal-related collectibles such as glassware, Australian bronzes, and jewelry.

Address: 11 W Washington St, Middleburg, VA 20117, United States

4. Trowbridge-Lewis Galleries

Trowbridge-Lewis Galleries
Credits: BearFotos / Shutterstock

Trowbridge-Lewis Galleries is exclusively focused on promoting original works from both American and international artists.

It is a paradise for art lovers as there are numerous artworks that send important messages to the viewers.

The gallery is packed with different artworks, including modern glass, steel & bronze sculptures, landscapes, and Asian antiquities from the Han Dynasties, Wei, Tang, and Ming.

Trowbridge-Lewis Galleries showcases the works of more than fifteen talented artists with a great focus on experimentation and education.

The gallery strives to create an interactive and friendly environment for people to view and talk about art.

Address: P.O. Box 2084, Middleburg, Virginia, United States

5. Goodstone Inn and Restaurant

Goodstone Inn and Restaurant
Credits: Goodstone Inn & Restaurant / Facebook
Goodstone Inn and Restaurant

Goodstone Inn and Restaurant is one of the best places to visit in Middleburg, VA, whenever you’re hungry. It is a popular restaurant in Virginia.

Goodstone Inn and Restaurant was listed in the top 100 best wine restaurants by Wine Enthusiast Magazine. It is one of the most romantic inns in USA Today.

It is a combination of an inn and a restaurant. It is located on a farm that spreads for two hundred and sixty-five acres.

Jamie Leith purchased the property in the 18th century to serve as a plantation. In 1996, the plantation was transformed into a Virginia country, featuring classic guest suites and rooms equipped with amenities such as flat-screen televisions, whirlpool tubs, and scenic views of mountains.

Goodstone Inn and Restaurant offer farm-to-table authentic French dishes carefully crafted by Jan Van Haute, the executive chef.

The restaurant offers an impressive menu featuring Shenandoah Valley lamb loins, Madeira caramel, and scallop ceviche with a selection of wines and signature cocktails.

Address: 36205 Snake Hill Rd, Middleburg, VA 20117, United States

6. Mt. Defiance Cidery and Distillery

Mt. Defiance Cidery and Distillery
Credits: Brent Hofacker / Shutterstock

Mt. Defiance Cidery and Distillery, founded in 2014, is known for producing handcrafted ciders and spirits.

Mt. Defiance Cidery and Distillery makes these products in small batches at similar facilities in Middleburg.

The Cidery focuses on traditional farmhouse mixes for dry cider composed of tasty flavors such as fresh pepper and ginger.

Some of the ciders co-fermented are available for tasting all year round ranging from blueberry to honey. Revival classic spirits are showcased at the distillery with an emphasis on “lost spirits” from the colonial era in the region.

Mt. Defiance Cidery and Distillery offers apple brandy, amber rum, straight bourbon, absinthe, and whiskey throughout the year. The two locations offer tours, food truck delights, and flight tasting.

Address: 207 W Washington St, Middleburg, VA 20117, United States

7. Popcorn Monkey

Popcorn Monkey
Credits: Mary Ann Madsen / Shutterstock

A unique gourmet popcorn store, Popcorn Monkey, was established by Deltone L. Moore, an entrepreneur, to offer the public quality gourmet popcorn.

Popcorn Monkey offers fresh popcorn made onsite for visitors throughout the year, along with several kinds of confections and candies.

They offer these treats in different artisanal flavors, which include tasty concoctions such as dark chocolate, delightful classics, and sea salt.

 You will also find other flavors like loaded potato, Old Bay-infused Old Crabby, and more, including a broad range of fudge flavors crafted in the facility, such as French vanilla, orange chocolate fudge swirl, and more.

Address: 101 W Federal St, Middleburg, VA 20117, United States

8. The National Sporting Library and Museum

National Sporting Library and Museum
Credits: Wisconsinjpc [CC BY-SA 4.0], Wikimedia Commons
National Sporting Library and Museum
The National Sporting Library and Museum, housed on a six-acre campus, is solely committed to preserving the cultural history and tradition of the country.

The Museum was established in 1954. It is found within the center of the gorgeous hunt country of Virginia, which features historic buildings.

Visitors get to discover a lot of history, beginning from the era of steeple chasing, angling, fox hunting, horsemanship, and shooting.

The National Sporting Library and Museum feature an extensive collection of exhibits relating to different sporting events, which are rotational.

You will find an animal & sports art of 400 years ago, Animal and sporting artists, and a wide range of educational programs offered all year round.

Students can also go through the enormous collection in the Library to broaden their knowledge.

Address: 102 The Plains Rd, Middleburg, VA 20117, United States

Also, check out the best of attractions and activities in Tysons Cornerand Fredericksburg for a fun vacation in Virginia.

9. Kizmetz

Credits: Kizmetz / Facebook

If you want to shop for unique items, add a visit to Kizmetz to your list of best things to do in Middleburg, VA, as it’s a place that offers rare items.

Kizmetz began as only a brick-and-mortar shop but currently offers a collection of rare and unique items you can’t get elsewhere.

The name of the store, “Kizmetz,” is a Turkish word for destiny, which implies that when you discover something by coincidence, it is bound to happen.

The store offers works made by artisans in the United States and other popular foreign locations. Every piece featured in Kizmetz was hand selected and acquired straight from fair Trade cooperatives and artisans.

You will have a great time browsing through the impressive collection of works. Their staff is friendly and ready to offer assistance.

Address: 116 W Washington St, Middleburg, VA 20117, United States 

10. The Byrne Gallery

The Byrne Gallery
Credits: The Byrne Gallery / Facebook
The Byrne Gallery

The Byrne Gallery was established in 1995 with an enormous collection of works, including outstanding services.

You will find a wide range of exhibitions. The Gallery also offers art installation, appraisal, and custom framing.

The major aim of the Byrne Gallery is to showcase the most talented artists in various mediums and styles.

They host exhibitions and receptions, which allow the people of the public a chance to meet and interact with artists in their mediums and style and also find out about the inspiration for their work.

Having existed for nearly three decades, the Byrne Gallery has achieved its goals. The Byrne Gallery is open only by appointment on Monday and Tuesday but is open to all from Wednesday to Saturday from 11 am to 5 pm and Sunday from 12 pm to 5 pm.

Address: 7 W Washington St, Middleburg, VA 20117, United States

11. Middleburg Common Grounds

Middleburg Common Grounds
Credits: Yulia Grigoryeva / Shutterstock

Middleburg Common Grounds is the number one spot in Middleburg if you ever need a place to enjoy a locally made coffee.

A perfect way to start your day in the city is through a delicious cup of coffee or any other beverage, along with some delightful light fares from the kitchen of Middleburg Common Grounds.

The shop features an outdoor patio where customers can relax and chat with friends, family, and colleagues.

Middleburg Common Grounds is a dog-friendly shop known for offering a variety of delicious drinks, including beers and wines.

They also offer freshly made homemade pastries, sandwiches, Avocado Toast, bacon egg & cheese, chicken salad, and more.

Address: 114 W Washington St, Middleburg, VA 20117, United States

12. 50 West Vineyards

50 West Vineyards
Credits: rawf8 / Shutterstock

If you’re looking for what to do in Middleburg, VA, visit 50 West Vineyards, an exceptional winery.

50 West Vineyards is owned and managed by Diane and Mike Canney. It was named after the historic road adjacent to the facility.

The winery expands over three thousand miles throughout the country within West Sacramento, Ocean City, California, and Maryland.

It is one of the biggest functioning wineries in Virginia, found on a charming bluff, offering a beautiful view of Bull Run mountains.

50 West Vineyards produces high-quality wines following the ancient World Wine production method with only the original Virginia fruit.

You can try out some of their productions, such as Sauvignon Blanc, Chardonnay, Vidal Blanc, and Albarino, offered in the winery’s taproom.

Address: 39060 John Mosby Hwy, Middleburg, VA 20117, United States

13. Boxwood Estate Winery

Boxwood Estate Winery
Credits: OPOLJA / Shutterstock

If you don’t want to go wrong in your choice of wines, drop by Boxwood Estate Winery; it is one of the best things to do in Middleburg, VA.

Boxwood Estate Winery is the realization of the long-time dream of Proprietor John Kent Cooke, the previous president and owner of the NFL Washington Redskins.

Cooke and his dedicated team are highly concerned with making classic white wines using the traditional method of Bordeaux with a Virginia touch.

The winery is located in a region drenched in Civil War American revolutionary history known as farms of world-recognized horses.

Now, this particular region is popularly known as a wine area. Boxwood Estate Winery covers nearly twenty-seven acres of a historic farm producing original Bordeaux varietals used in producing Cabernet Franc & Sauvignon Blanc, Cabernet Sauvignon, and Merlot.

 Address: 2042 Burland Ln, Middleburg, VA 20117, United States

14. Middleburg Ghost Tours

Middleburg Ghost Tours
Credits: Middleburg Ghost Tours / Facebook
Middleburg Ghost Tours

Are you a fan of creepy and scary stories and places? If yes, Middleburg Ghost Tours is something you shouldn’t miss in Middleburg.

Middleburg Ghost Tours offers guided strolling tours to some of the most haunted sites in historic Middleburg.

They take you on a journey back in time through the region’s haunted history by listening to stories about numerous hauntings recorded within the historic district of Middleburg.

They boast of offering visitors nothing less than an amazing experience, regular tours, mostly on Fridays and Saturdays at 8 pm, and private tours by appointment.

Middleburg Ghost Tours is an experience every visitor interested in hunt country should add to their itinerary of fun things to do in Middleburg, VA. It is a family-friendly adventure that children would absolutely love and wouldn’t forget in a hurry.

Address: Middleburg, VA 20117, United States

15. The Fun Shop

The Fun Shop
Credits: The Fun Shop / Facebook
The Fun Shop

A family-owned and managed business, the Fun Shop, was established by Nancy Lee Allen in 1956 in Middleburg.

The shop is run by her two daughters, who have vouched to respect her values and legacy. Betsy Allen Davis serves as the office manager, while Page Allen is the Buyer and manager of the shop.

It is housed in a facility of 6,000 square feet and packed with merchandise ranging from children’s items to home decor and gifts.

The Fun Shop offers children’s toys, bed & bath products, cards & party goods, clothing, lamps, books, kitchen & gourmet items, stationery, gift items, shades, and many more.

The shop offers essential personal services such as the special ordering of products, free gift-wrapping, and personal shipping & shopping services.

Address: 117 W. Washington St., Middleburg, VA, 20117 United States

Check out the things to do in Blacksburg, and things to do in Woodbridge for a memorable exploration of Virginia.

16. Middleburg Antique Gallery

Middleburg Antique Gallery
Credits: Aris-Tect Group / Shutterstock

Are you searching for a place to purchase a gift for a loved one? Then, Middleburg Antique Gallery is the perfect place. It should be on your Middleburg to-do list.

Middleburg Antique Gallery ensures there is something for everyone featuring about forty-five dealers offering European, state, and local antiques.

The Gallery also offers the finest American, European, and English furniture made of English oak, walnut, and mahogany, including Satinwood and Rosewood pieces.

You will find an impressive collection of Scottish and English furniture featuring several options depending on clients’ budgets and preferences.

Middleburg Antique Gallery offers a variety of lamps, antiquarian books, jewelry, coin silver, American sterling, sporting & fishing antiques, and oriental jugs.

You can stop by the shop, glance through the displayed antiques, and have an amazing shopping experience.

Address: 107 W Washington St, Middleburg, VA 20117, United States

17. Potomac Overlook Regional Park

Potomac Overlook Regional Park
Credits: Potomac Overlook Regional Park / Facebook
Potomac Overlook Regional Park

Potomac Overlook Regional Park is located along the Potomac River on a wooded terrain of seventy-acre.

The Park features hiking trails that are ideal for both beginner and experienced hikers, offering gracious views of the environment.

There is an educational center known as the James I. Mayer Center, where adults and children get to learn a lot about the relationship between nature and humans.

Potomac Overlook Regional Park features a charming educational garden for children of all ages, including adults.

The Park is a venue for outdoor summer events and a favorite place for kids’ summer camps. In addition, there is a picnic area where families and friends can enjoy a delicious meal or snacks together.

Address: 2845 North Marcey Road, Middleburg, VA 22207, United States

18. Second Chapter Books

Second Chapter Books
Credits: Jure Divich / Shutterstock

Is there any book you have been looking for, for a while, and you have lost hope of finding it? Then, don’t miss the chance to hold your favorite book with your palms.

Second Chapter Books offers new and second-hand books to all individuals, regardless of age.

The store is owned and operated by a dedicated individual passionate about providing a safe and calm environment for visitors to sit and read.

There are three rooms fully packed with carefully selected books and rare publications that are difficult to find.

Second Chapter Books offers newspapers, handmade cards, gifts, games, journals, maps, puzzles, bookmarks, calendars, and more.

Address: 13 East Statesgton, Middleburg, VA 2011. United States

19. King Street Oyster Bar

King Street Oyster Bar
Credits: K321 / Shutterstock
Fried Oysters

Are you in a celebratory mood or want to unwind with some friends? King Street Oyster Bar is always open for you.

King Street Oyster Bar is one of the city’s most popular places, attracting numerous locals and visitors.

As a favorite spot, King Street Oyster Bar is open throughout the week. It is the number one place for fresh oysters.

There is outdoor seating where you can relax, especially during the hot days, for some fresh air; you can also find a seat indoors at the bar.

King Street Oyster Bar offers Raw Oysters on the Half Shell, tuna tacos, Lobster Roll Warm, Fish and Chips, Fried Oysters, Oysters Rockefeller, Eggs Benedict, Seafood Pasta, and more.

The happy hour comes with discounts for beers, cocktails, snacks, wines, and oysters; their services are second to none.

Address: 1 East Washington St, Middleburg, VA 20117, United States

20. The Crème de la Crème

Crème de la Crème
Credits: PH888 / Shutterstock

The Crème de la Crème is comprised of three mortar and brick shops, including a French-Italian online boutique.

Their main store is situated in the middle of Hunt Country in Middleburg, with other branches located in downtown Maryland and Frederick in Virginia and Richmond, respectively.

The moment you step into any of their boutiques, you will be embraced by the lasting fragrance of their signature candles.

The Crème de la Crème is filled with unique treasures that can serve as gifts for your loved ones and home.

You can find jewelry, home fragrance, gifts, signature candles, bath & body products, garden accessories, and the art of the table items.

Address: 23 E Washington St, Middleburg, VA 20118, United States

21. The Middleburg Tennis Club

Middleburg Tennis Club
Credits: Ewebphoto / Shutterstock

Looking for what to do in Middleburg, VA, to spend your leisure time? The Middleburg Tennis Club is the best choice for you.

The Middleburg Tennis Club was established in 1969 as a recreation center that spans more than ten acres.

It is a members-only center featuring facilities and courts, including a swimming pool and a fully equipped fitness center.

The club offers camping and tennis classes for those who want to go on a camping adventure or master their skills in tennis.

The Middleburg Tennis Club offers an inviting and welcoming environment with a relaxed and simple feeling for everyone to enjoy.

The onsite restaurant offers different dishes, including sandwiches, salads, entrees, and many more.

The club also offers Labor Day cook-out, Memorial Day cook-out, special club dinners, Mother’s Day Brunch, and Father’s Day cook-outs.

Address: 1777 Zulla Rd, Middleburg, VA 20117, United States

22. Cuppa Giddy Up

Cuppa Giddy Up
Credits: Bojan Pesic / Shutterstock

Before you start your day-to-day activities in Middleburg, stop by Cuppa Giddy Up for a quick and flavorful cup of coffee.

Cuppa Giddy Up has been in existence for about fifteen years and has continuously offered the best services in the region.

They take pride in serving only the freshest and most delicious coffee mixtures, including specialty beverages with other delightful snacks.

This coffee shop is a popular place for coffee lovers in the town and is a meeting point for many locals and visitors.

Cuppa Giddy Up also offers hot chocolate, mocha, Americano, espresso, cappuccino, chai, smoothies, Italian soda, and more.

In addition, visitors can purchase cakes, bagels, muffins, cookies, brownies, and croissants. Cuppa Giddy Up offers catering services for various special events within the area.

Address: 8 E Washington St, Middleburg, VA 20117, United States

23. The Fox Chase farm

Fox Chase farm
Credits: Fox Chase Farm, Middleburg, VA / Facebook
Fox Chase farm

Are you planning an event? If you need a fantastic venue in Middleburg, check out the Fox Chase farm.

The Middleburg Barn is located at Fox Chase farm as a spectacular barn ballroom that serves as a platform for shows and numerous equestrian competitions.

It is a favorite place for weddings and several private events featuring contemporary amenities, which are necessary when organizing a fun-filled and stress-free event.

Although most weddings are usually from one hundred to two hundred and fifty, couples can invite up to three hundred and fifty persons.

The Fox Chase farm features a scenic picnic pavilion where couples can carry out a cocktail reception as guests get to enjoy cocktails.

Address: 23320 Foxchase Farm Ln, Middleburg, VA 20117, United States

Take to exploring other cities of Virginia. Check out our list of things to do in Waynesborothings to do in Front Royal, and things to do in Cape Charles.

Plan Your Trip to Middleburg

Middleburg is one of those cities in the state of Virginia that depicts how a typical developed American city should be, irrespective of size.

There are lots of fun and thrilling activities waiting for you to explore in Middleburg. You’re sure to have fun.