Middleburg

It’s no secret that we love Middleburg. Located about 40 miles outside of D.C., the community lifestyle in this small town is much slower-paced than surrounding areas. Rolling hills and horse farms make up most of the bordering landscape, offering the true Virginia experience. Middleburg has been named the capital of horse and hunt country, as well, attracting many prestigious visitors. It’s a great place to live out your equestrian dreams and discover some incredible history. 

Things to Know

Outdoor Entertainment

Tour Virginia’s Wine Country

Middleburg is one of the top 10 wine destinations in the world. Greenhill Winery and Vineyards, Chrysalis Vineyards, and 50 West Vineyards are all some of our top recommendations. While you’re here in town, look over some of Virginia’s best views and taste some of our country’s most famous spirits. 

The Virginia Fall Races

Hosted at Glenwood park in the middle of one of Virginia’s most beautiful seasons, the Virginia Fall Races is an event you shouldn’t miss! There’s food, vendors, mild autumn air, and fun for the whole family. Not to mention, oh so many horses! 

Window Shopping

This is one of Middleburg’s most popular attractions. And there’s no wonder. With all the incredible architecture and preserved civil war history, a simple stroll down Washington Street is all you need to fall completely in love. Plus, the French boutiques and gift shops are endless. We love visiting some of our favorites, The Fun Shop, The Christmas Sleigh, Second Chapter Books, and Crème de la Crème. Feel like a warm cup of coffee? Cuppa Giddy Up is the cutest little brick coffee shop. Plus, it’s right next door to our Middleburg office, so come say hello with a latte in hand.  

Community Center

A dreamy yellow building at 300 West Washington is the home of Middleburg’s illustrious Community Center. It hosts many of Middleburg’s town events, including drive in movie nights during the summer months, a farmer’s market, fitness classes, summer camps, and Concert on the Steps. They are also a popular wedding venue, feature a community pool, and host numerous art classes and activities for kids. 

The National Sporting Library and Museum

The NSLM has numerous events and exhibits open to the public. If you live for horses, books, and foxhunting, this is the place for you. The research library was built in 1999 and is open for free public use. There’s also a fantastic art museum that seeks to bring horses alive through art and literature. It’s Virginia’s destination for everything equestrian.

Dining & Night Life

Mt. Defiance Cidery and Distillery

Has some of the best hard cider blends around. All made from local apples, Mt. Defiance is particularly famous for their absinthe and sweet vermouth. Their friendly customer service and excellent tastings put them on our list of top places to stop while in Middleburg. 

Side Saddle Café

Can’t get enough of Middleburg’s equestrian side? We can’t either. That’s why we suggest dismounting for lunch at the Side Saddle Café. This unique restaurant offers breakfast and lunch from farm to table. All produce and meats come straight from Fields of Athenry Farm, also a business of the owner’s. Virginia’s southern charm really shines through fantastic customer service and delicious scrapple. 

The Red Fox Inn

For such a small and quaint little tavern, the Red Fox Inn has experienced more than its share of big historical events. They’ve been one of Virginia’s top stop locations since the revolutionary war, and housed important guests like John F. Kennedy, Tom Cruise, Paul Newman, and perhaps even George Washington. Experience some of Middleburg’s best lodging and fine dining. 

Best Thai Kitchen

No wonder the food’s so good! The sweet family owners of Best Thai Kitchen bring their skills all the way from Thailand. We recommend the panang curry or the fantastic house special, their pad Thai. They truly live up to their name as one of the best.