Amazing Things to Do in Middleburg, VA: Attractions, Wineries & Hidden Gems

Things to do in Middleburg, VA start with a historic district less than a mile long but dense with attractions: America's oldest continuously operating inn, a Forbes Five-Star resort, boutique wineries producing Bordeaux-style blends, and a horse-and-hunt culture dating to 1728. Located in Loudoun County roughly 50 miles and about an hour from Washington, DC, Middleburg is known as America's horse and hunt country capital, drawing everyone from Jackie Kennedy Onassis to sitting presidents to its brick-lined streets. Whether you're planning a single Middleburg day trip or a full weekend, this guide covers every major Middleburg VA attraction in one place.

Best Things to Do in Middleburg, VA — Quick Reference

Middleburg VA Attractions: Explore Historic Downtown

The top Middleburg VA attractions start with the historic downtown itself, dating back to 1728, when a fieldstone tavern established by a cousin of George Washington became what's now the Red Fox Inn & Tavern — still operating today as America's oldest continuously running inn. Among Middleburg's best-known attractions is the National Sporting Library & Museum, founded in 1954 as the nation's leading research resource on equestrian and outdoor pursuits, with a collection of more than 16,000 books and a fine art gallery on the town's western edge. The historic district is less than a mile long but dense with chic boutiques, art galleries, and cafés lining brick-edged streets — a slow walk down Washington Street covers most Middleburg virginia things to do in under two hours.

Middleburg Wineries: The Best Wine Tasting in Town

Middleburg wineries anchor the town's identity as the heart of Loudoun County's wine country, with several standout names within a short drive of downtown. For a private wine tour covering multiple Middleburg wineries in one day, see our Virginia wine tour service — particularly useful given that no rideshare operates in town.

1. Boxwood Estate Winery. One of the premier Middleburg wineries, specializing in Bordeaux-style blends, with wine-blending experiences walking visitors through combining Merlot, Cabernet Sauvignon, and Cabernet Franc. Appointment required — max 12 per group.
2. Greenhill Winery. Widely regarded as one of Loudoun County's foremost boutique wineries, set among rolling vines and horse farms with an elegant tasting room and picnic spaces. Walk-ins welcome daily noon–6 PM.
3. Cana Vineyards. Award-winning estate reds and rosés in a family- and pet-friendly setting with a heated Sunset Pavilion — one of the few Middleburg wineries with a genuine year-round outdoor tasting option.
4. Chrysalis Vineyards. Focused on the Norton grape — Virginia's official state grape — with a farm-to-table approach integrating food production directly onto the winery grounds. A short drive from Middleburg proper.

Beyond wine, Lost Barrel Brewing, set on a historic horse farm just outside town, rounds out the Middleburg wineries day for groups with both wine and beer drinkers — more than 20 handcrafted beers and seltzers, a spacious taproom, and a biergarten with fire pits.

Horse Country Experiences

Middleburg's identity as America's horse and hunt country capital runs deep. The countryside surrounding the town is dotted with thoroughbred horse farms visible along stone-walled country lanes — a defining Middleburg VA attraction even for visitors not participating in any equestrian activity directly.

Middleburg Spring Races

The Middleburg Spring Races — a century-old steeplechase tradition — offer visitors a direct look at the region's competitive riding culture during the spring season, drawing crowds for a genuinely local, historic sporting event.

Christmas in Middleburg

The annual Christmas in Middleburg celebration includes the Middleburg Hunt & Hounds Review — a mile-long parade featuring horses, hounds, and riders in full traditional hunting regalia through the decorated downtown streets, one of the most photogenic things to do in Middleburg VA in December.

Middleburg Shopping: Boutiques, Antiques & Galleries

Middleburg shopping runs the length of the historic downtown, from equestrian-themed boutiques to fine art galleries. The Middleburg Antique Emporium is the standout stop — set up like a tastefully decorated Victorian home, it's one of the most memorable Middleburg VA attractions for antique and vintage collectors, and a genuine alternative to typical small-town retail.

Middleburg Restaurants: Where to Eat

Outdoor Activities Near Middleburg

Sky Meadows State Park

Sky Meadows State Park, a short drive from Middleburg, offers extensive hiking trails through open meadows and wooded terrain with panoramic Blue Ridge views — the strongest outdoor add-on to a Middleburg day trip for anyone who wants more than a wine and shopping itinerary. Budget 3–5 hours.

Scenic Drives

The narrow, stone-walled country lanes surrounding Middleburg — winding past horse farms, vineyards, and historic estates — are worth the drive independent of any specific destination. A slow loop through the surrounding countryside takes about an hour and is one of the more underrated things to do in Middleburg VA for first-time visitors.

Best Hotels & Inns in Middleburg

Perfect One-Day Middleburg Itinerary

1. Morning: Historic downtown walk and Middleburg shopping. Start on Washington Street — boutiques, the Middleburg Antique Emporium, and a coffee stop before the Middleburg wineries open.
2. Midday: National Sporting Library & Museum. A focused hour on the region's equestrian history — one of the most distinctive Middleburg VA attractions for visitors curious about what makes this town different from other Virginia wine country stops.
3. Afternoon: One or two Middleburg wineries. Boxwood Estate for a blending-focused experience (appointment required, max 12 per group), or Greenhill Winery for a walk-in tasting.
4. Evening: Middleburg restaurants — Red Fox Inn or Harrimans. Red Fox Inn's Tavern for the historic setting; Harrimans at Salamander for countryside views and an elevated Virginia cuisine experience.

Weekend Itinerary From Washington DC

For a fuller weekend rather than a single Middleburg day trip, pair the town with a night at Salamander Middleburg or the Red Fox Inn, adding Sky Meadows State Park for a morning hike and a second winery visit on day two. Middleburg is one of the strongest entries on our broader guide to weekend getaways from DC — particularly for couples or anyone building a wine-country weekend without traveling more than an hour from the city.

How to Get to Middleburg

Driving is the most common way to reach Middleburg — roughly 50 miles and about an hour from downtown DC via Route 50. For a Middleburg wineries day specifically, a private car service removes the need to designate a driver after tasting at multiple stops. For airport arrivals, Dulles Airport (IAD) transfers are the most practical given Dulles is the closest major airport to Middleburg; DCA and BWI both require a longer additional drive west. Full Loudoun County visitor information is also available via Visit Loudoun.

Frequently Asked Questions