7 Horsey and Wine-y Things to do in Middleburg VA

WHY GO: Fox Hunting and Wine rule the day in Middleburg VA, a small well-to-do hamlet in Loudoun County outside Washington DC. So much so, you can stay in a 250+ year old Inn called the Red Fox, or in a new posh country estate centered on equestrian activities, and visit some fantastic wineries doing very innovative things.

Oh, and did we mention the distillery that excels at making traditional Absinthe? For a town of 600 people, there’s a lot to experience while visiting Middleburg, including a world-class Sporting Museum, great restaurants, and cool shops.

Unplug for a couple of days in one of the most charming small towns on the East Coast, and wile away some hours where the hospitality is heart-felt. We let you in on all the details below.

For a winery-hopping getaway, check out our greater Loudoun County VA post.

Middleburg is on our list of 20 Surprisingly Romantic Getaways in VA. Check it out if you wish to explore the state further.

Looking for someplace dreamy outside of Virginia? Check out our 150 Best Romantic Getaways in the Northeast US (Virginia to Maine).

Things to Do In Middleburg VA And Nearby

National Sporting Library and Museum Middleburg VA
National Sporting Library and Museum Middleburg VA

VISIT: The National Sporting Library and Museum

What exactly is “Sporting” and how is is different from, say, Basketball, Baseball, and Football? Well, explains one docent, the National Sporting Library and Museum is all about “old country sports. If they did it in a Jane Austin novel, they’ve got exhibits about it here.”

Artifacts are arranged on two floors throughout two connected buildings. With four temporary shows a year and a permanent collection of paintings, prints, and sculptures displayed in new state of the art galleries, there is a lot to see and ponder. This starts with the 2011 museum expansion itself,  built to blend in with the historic part of the home.

Of Horse Heads and More

Still Water National Sporting Library and Museum Middleburg VA
Still Water National Sporting Library and Museum Middleburg VA

Right away, the 9 ft. tall sculpture of a vertical horse head, “Still Water” by Nick Fiddian Green, commands attention. Those who’ve been to England will recognize it as the smaller of an astonishing 30 ft version that looms near London’s Marble Arch.

Silver Coach National Sporting Library and Museum Middleburg VA
Silver Coach National Sporting Library and Museum Middleburg VA

Besides horsey things; fly-fishing, wing shooting, grouse hunting and more are represented here.

Ogle a solid silver scale model coach  – part of an outrageously extravagant dining room set. With lanterns that swivel, rolling wheels, and a working break system. “If you hooked it up to guinea pigs, it would actually go,” a docent exclaimed.

Carriage Driving is still a competitive sport here. On any given day you might see antique coaches going up and down the dirt roads of Loudoun County.

National Sporting Library and Museum Middleburg VA
National Sporting Library and Museum Middleburg VA

You might feel compelled to spend some time in this Museum, with all there is to see. But don’t leave without checking out the main-floor Library, even if you have no interest in researching the Sporting Life.

Check out the antique weathervanes and trophies on shelves, and then….. stay. Staff here welcome those who just want a quiet place to work or study. Admission to the library and Wi-Fi is free, it’s air-conditioned, and there are tables and cozy nooks.

Forged-Edged Books and Terry Roosevelt’s Handwritten Essays

Book Edge Art National Sporting Library and Museum Middleburg VA

For a real treat, plan ahead and arrange for a special tour of the temperature controlled rare-artifacts library downstairs where antique books, periodicals, and other rare collectables are held. Ask to see a “fore-edged painting” book – one in which the book’s edge, when fanned out, reveals a painted scene.

There’s a 1752 calfskin bound ledger book from a French estate, itemizing, in someone’s beautiful handwriting, purchases and expenses for what must have been very spoiled horses in the stables.

Teddy Roosevelt Essay National Sporting Library and Museum Middleburg VA
Teddy Roosevelt Essay National Sporting Library and Museum Middleburg VA

My favorite bound book, however, is Teddy Roosevelt’s handwritten essay (not a copy), defending Fox Hunting as an American Sport. Study his actual strike-throughs, substitutions, and notations to get a glimpse into the President’s working mind. These days, with “delete” and “edit” capabilities on our electronic devices, it’s a writing process we no longer see. Check website for hours and admission fees.

Jenny McCloud, Chrysalis Vineyard, Middleburg VA
Jenny McCloud, Chrysalis Vineyard, Middleburg VA

GO/TASTE: Chrysalis Vineyard

Chrysalis Vineyard owner, Jenny McCloud, marches to the beat of her own drum. She has a billion ideas and the energy and gumption to see many of them through. McCloud has been turning out award winning wine, specializing in unique Spanish and French varietals and the native Virginia grape, Norton, for quite some time.

But McCloud has also enlisted experts to make cheese and bake bread on the premises as part of the “Ag District,” which connects visitors to Loudoun’s rich agricultural heritage. She has gone so far as planting Heritage Wheat for her fresh-baked breads.

House-made cheese utilizes milk from cows grazing on her 412 acres. See cheese aging and processing in basement rooms. Just wandering around puts you in a good, DIY mood.

Chrysalis Vineyard, Middleburg VA
Chrysalis Vineyard, Middleburg VA

Enter into the design-forward “commerce floor” to pick up said bread, cheese, and a bottle of your favorite wine. Take them home, or eat and drink on the top floor either indoors or out. Either way, enjoy smashing views of the surrounding hills and farmland.

Jenny McCloud-owner-Chrysalis Vineyard, Middleburg VA
Jenny McCloud-owner-Chrysalis Vineyard, Middleburg VA

Though “big in the wine world here,” McCloud is an amiable sort – what many would call “a hoot.” Far from a wine-snob, she loves giving her table wines names like “Snobby Bitch White Sangria.” McCloud’s Patio Red and Patio White, with CO2 added for slight effervescence, are mildly sweet and very popular.

Mt. Defiance Cidery Middleburg VA
Mt. Defiance Cidery Middleburg VA

GO/TASTE: Mt. Defiance Cider and Distillery

Named for the Civil War skirmish and “family feud” up the road, Mt. Defiance Cidery and Distillery are two separate entities. The cidery is a bit north of town on a hill in a barn-like building. Though the cidery doesn’t grow its own apples (it gets its juice from nearby Rinker’s Orchards), it makes traditional blends of farmhouse dry cider and its own Sweet Vermouth, Apple Brandy and Cider Pommeau – an apple “port.” Come to the tasting barn, and you can try them all, as well as other ciders on draft.

Mt. Defiance Distillery Middleburg VA
Mt. Defiance Distillery Middleburg VA

The Mt. Defiance Distillery is right in downtown Middleburg, in an old service station. Its claim to fame is something you don’t see much in distilleries these days. Absinthe.

Mt. Defiance makes this grass-colored spirit the traditional way, with herbs and wormwood grown in their own gardens.

Absinthe Experience Mt. Defiance Distillery Middleburg VA
Absinthe Experience Mt. Defiance Distillery Middleburg VA

Walk in, ask for a taste, and you’ll learn why absinthe was so maligned (its prohibition had more to do with competition and politics than any danger drinking it), how it’s made, and the traditional method of serving it.

True absinthe is a transparent forest green. (As opposed to fake neon green). Diluted by ice water that drips from a designated fountain, the concentrated Absinth turns a cloudy yellow – called “la louche.” Though the spirit itself is a matter of taste, the absinthe ritual is fascinating and worth a stop in to see.

TASTE: More Middleburg Virginia Wineries and Breweries

Boxwood Winery

A stunning farmland winery owned by former owner of the Washington Redskins (NFL), John Kent Cooke.

Greenhill Winery Vineyards

One of the top wineries in Virginia’s Hunt Country, celebrating local terroir with 100% Virginia wines.

Lost Barrel Brewing

Guests rave about the food, wine, craft beer and cocktails, and all around “chill” ambience at Lost Barrel.

Downtown Middleburg VA
Downtown Middleburg VA

SHOP: Middleburg Main St.

The town of Middleburg is not very big, but you’ll find some cute clothing, antique, art galleries, and gift shops on main streets. Among them, Highcliffe Clothiers – an old fashioned haberdashery men and women; Middleburg Antique Gallery – with “something for everyone;” and Creme de la Creme – a French and Italian country home goods store. Slow down and smell the soy candles.

Where to Eat in Middleburg VA

Red Fox Tavern Middleburg VA

EAT: The Tavern and Night Fox Pub at Red Fox Inn

(See Below Under Where To Stay)

Cauliflower Salamander Resort Restaurant Middleburg VA

EAT: Gold Cup Wine Bar – Salamander Resort

Just half a mile from “downtown,” it’s worth it to eat at the Salamander Resort even if you don’t stay. There are several ways to partake: sign up for a cooking class in the professional kitchen, book a table at the swanky Harriman’s, or grab a seat in the more casual Gold Cup Wine Bar, which showcases some cultishly good Asian influenced dishes. My favorites were the simply dressed Poke and Crispy Sesame Cauliflower: both served in eye-catching bowls.

Market Salamander Middleburg VA

EAT/PROVISION: Market Salamander

Find Market Salamander right in town, across from Mt. Defiance Distillery. Pick up sauces, jams, and prepared foods. The deli serves the freshest of sandwiches and salads for a quick bite.

EAT: Locals Recommend

Goodstone Inn Restaurant for fine American and French cuisine with an extensive wine list; Middleburg Common Grounds for coffee; The Upper Crust Bakery for baked goods, soups, sandwiches and ice cream; King Street Oyster Bar for seafood and raw bar,

Where to stay in Middleburg VA

Red Fox Inn and Tavern Middleburg VA
Red Fox Inn and Tavern Middleburg VA

STAY: Red Fox Inn and Tavern

The Red Fox Inn and Tavern in Middleburg VA, established in 1728, is one of the oldest and finest inns in the country. So it’s not difficult to imagine Bold Faced Names like Elizabeth Taylor and Jackie Kennedy overnighting here during fox-hunting seasons of yore.

While the restaurant and several rooms are located right on Main Street, most guest rooms are scattered in cottages a block from the busy intersection. Pictures and sculptures of horse and riders, dogs, roosters, and other genteel pursuits are found at every turn.

First Impressions of Red Fox Inn and Tavern

Cottage Red Fox Inn Middleburg VA

If you want to stay one step from the restaurants and shops of downtown Middleburg, and your skeptical, beaten-down heart yearns for the balm of a genuine, relaxed, and friendly welcome, this is your place. Pull in to the parking lot, park in a temporary unloading spot, and walk past the outdoor patio into the small reception area on the 2nd floor (upstairs from the street Tavern entrance). Check-in feels like an embrace.

Rooms at Red Fox Inn and Tavern

Guest Room Red Fox Inn Middleburg VA

Each room and suite is country-luxe. Burnished wood floors extend into charming antique-filled bathrooms sporting pedestal sinks and bathtub showers. The doilies on side tables are elegant, not kitschy.  Appropriately, horse, quail, and duck prints that hang on the walls establish a sense of place. Best of all is the pillowy bedding – so downright comfy, I wanted to take it home.

Red Fox Inn Walkway Middleburg VA

Most guest rooms are a walk from the restaurant, so The Red Fox Inn offers crack of dawn coffee brought right to your room. At your preferred hour! As a caffeine addict, this perk remains one of my all-time favorites: particularly because the housekeeper brought it to me exactly on time – the mark of a well-run inn.

Breakfast and Dinner at Red Fox Inn

Red Fox Tavern Middleburg VA

Picture a whitewashed fieldstone-walled hunt club with fireplace, wood tables, low ceiling. And then add excellent food. Within a warren of rooms, the Tavern, shade-lamp votives aglow, features Southern cuisine with local produce.  Observed on a cool autumn Monday night, this is one of the most popular restaurants in town – for a very good reason. Virginia Peanut Soup, Shrimp and Grits  Rack of Lamb, 16 oz. Ribeye, and more are all expertly prepared. Everything arrives at your table with a healthy dose of Southern hospitality. I’d return for the Hickory Bourbon Glazed Salmon on a bed of grits and sweet, noodled carrots. Decadence without guilt.

In the morning a full made-to-order breakfast comes complementary with the room, and is served in the Tavern. On the menu is a Veggie Omelet or Huntsman’s Breakfast (2 eggs any way, potatoes, bacon, toast, etc), and only-in-the-South offerings like the Fried Green Tomato Benedict. Sourced locally, everything on the plate tastes fresh from the farm.

Salamander Resort Restaurant Middleburg VA

STAY: Salamander Resort and Spa

Sheila Johnson, co-founder of BET (Black Entertainment Television), and one of the wealthiest African Americans in the USA, modeled Salamander Resort and Spa, her ultra-luxe 340-acre resort, on her own country house.

Loudoun County is known for wine and fox hunting. There are touches of both, along with Johnson’s personal effects, throughout the common areas and guest rooms.

Lobby Living Room Salamander Resort Middleburg VA

Johnson wants you to feel at home. So, post check-in, welcome into an alluring “Living Room.” Its high ceilings, fireplace, fine furniture, equestrian paintings, and a windows overlooking verdant horse country, puts you into a royal frame of mind. After all, they don’t call fox hunting and horse-racing the “Sport of Kings” for nothing.

Salamander Resort Middleburg VA

Of course, you can sign up to ride horses on the property. But fans also look forward to these seasonal programs: Yoga in the Stables; “Cocktails With Cupcake” – the miniature pony; Sunset Bike Ride; Zombie Archery; Treetop Tours; Nordic Trekking – and dozens more fitness, spa, art, and cooking classes. A virtual bonanza of offerings – no need to leave the property. Rates from $450 per night.

Middleburg VA Getaway Pin


  • Malerie Yolen-Cohen

    Malerie Yolen-Cohen is the Author of the cross-country travel guide, Stay On Route 6; Your Guide to All 3562 Miles of Transcontinental Route 6. She contributes frequently to Newsday, with credits in National Geographic Traveler, Ladies Home Journal, Yankee Magazine, Shape.com, Sierra Magazine, Porthole, Paddler, New England Boating, Huffington Post, and dozens of other publications. Malerie’s focus and specialty is Northeastern US, and she is constantly amazed by the caliber of restaurants and lodging in the unlikeliest places.

    View all posts

3 thoughts on “7 Horsey and Wine-y Things to do in Middleburg VA”

  1. Middleburg is where i spent many days and nights in the 20’s and now at 50 im still loving this town i call home. The Red Fox Inn is a wonderful place to stay and dine! Everything was wonderful from our stay to our lovely dinner and our server Grant Russell!! If you enjoy wine without making the trek to NAPA this is a wonderful weekend of tasting!

  2. Hi Ashley – thanks for reading and commenting. I can see why you love Middleburg. It’s a special place!

  3. I grew up in Middleburg til I turned 23 years old. I then moved to New England and became a Skier and worked for the Federation of USA Sking team. I recently moved back to the area and so many things have changed. I have enjoyed all the new stores and shops. Middleburg is a very adorable place with so much to offer.
    Its the town that never changes and been so many generations.

Comments are closed.