Destination Middleburg

Authentic Lifestyle Events in Horse & Wine Country

Horse & Wine

Known for over a century as the nation’s Hunt and Horse Capital, Middleburg represents the paradigm of equestrian tradition and excellence.  The gently rolling hills of the Piedmont create the perfect turf and terrain for a multitude of equestrian sports. Horses here are as ubiquitous as stone walls and day lilies.  That same landscape has proved ideal ground for wine-making grapes, and the region boasts dozens of Virginia’s finest wineries.  Not a horse or wine enthusiast?  The boundless countryside offers a vast array of outdoor sporting activities, from hunting and hiking to fly-fishing and falconry.

As your connection to sophisticated sporting and lifestyle events in the Virginia Piedmont, Destination Middleburg will custom-craft exclusive private outings using thousands of acres of historic hunt country land, licensable hunting and fishing spots and expert guides.  Whatever your desire, we’ll design detailed concepts, provide logistical plans, then work tirelessly to execute them flawlessly.

Custom Group Offerings:

Equestrian Experiences

  • Twilight Polo – Meet Players and Riders
  • Polo 101 – Learn and Play
  • Hunt Send-offs (join a hunt if experienced) 
  • Roading, Walking the Hounds
  • Field-Side Polo Brunches 
  • Steeplechase Rail Picnics 
  • Carriage-Driving Tours 
  • Trail Riding 
  • Farm & Stable Tours
  • Jump to It (professional demos)
  • Training Track Morning Workouts
  • Shoe-In (farrier demo)

Wine Country Outings 


  • Wine-Tasting Tours (via antique cars, hot air balloon, carriage)
  • Movies & Moonshine (outdoor screening at local vineyard)
  • Barn Parties
  • Stars & Cigars
  • Pinot Poker Parties 
  • Bonfires & Bourbon 
  • Rhythm & Booze 

The Sporting Life


  • Sporting Clays & Skeet Shooting
  • Falconry Exhibitions (on horseback, too) 
  • Retriever Demonstrations & Training 
  • Trick Shooters
  • Fowl and Game Hunting
  • Fly-fishing on the Shenandoah 
  • Hiking & Cycling 
  • Archery & Target Ranges
  • Golf
  • Kayaking on Goose Creek or the Shendaoah

From Village to Village


  • Antiquing & Boutiquing 
  • Civil War Site Excursions 
  • General Store Cycling Tours (Philomont, Atoka, Bluemont, Millwood) 
  • Village Pub Crawls 
  • Seasonal Fruit-Picking and Farmer’s Marketing 
  • Farm to Table Dining Experiences 
  • Virginia Native Plant Tours
  • Mechanicsville (work with/on vintage cars)