Virginia’s Most Picturesque Small Town Makes A Dreamy Fall Getaway

It’s autumn in Middleburg, Virginia, and the landscape is turning itself into a painting. Shades of fire and flame illuminate maples and hickories, while towering oaks and beeches change to copper before emptying their branches. Roads leading to and from this tiny town in Loudoun County are lined with low, gray stacked-stone walls that evoke centuries past. Beyond them, flaxen-tailed horses stand on the rolling hills, which are still green in mid-October. Leafy vines bearing clusters of grapes extend in perfect rows next to picturesque wineries and their tasting rooms, each with scenic views of the Piedmont region.  

There’s no finer time to visit than the fall, not only for the changing landscape, but for a host of seasonal traditions that define this place, most notably its devotion to all things equestrian-related. Read on to learn more about the town and plan the perfect autumn getaway. 

Check Out A Horse Competition

Long a destination for well-heeled visitors escaping Washington, D.C., this place is called The  Nation’s Horse and Hunt Capital. Annual events, such as The Virginia Fall Races’ steeplechase in the spring and the Theodora A. Randolph Field Hunter Championship in autumn, bring equestrians, trailers of horses, and thousands of spectators to town. 

Make A Stop At The Red Fox

Middleburg’s proximity to D.C. (it lies around 20 miles from Washington Dulles International Airport) played a major role in its eventful past. During the 20th century, the town hosted a starry roster of guests and residents, including the Kennedys and Elizabeth Taylor, all of whom spent time at The Red Fox Inn & Tavern. As the oldest property in the area and one of the longest continually operated inns in the U.S., the nearly 300-year-old structure made of local fieldstone anchors the downtown. 

Former President John F. Kennedy once made an address upstairs in the spot where you can now find the Night Fox Pub, and the inn’s check-in operations are housed in a room known to have been beloved by Taylor. “The buildings and businesses here have roots,” says Matilda Reuter Engle, a seventh-generation Middleburg resident and the proprietor of The Red Fox Inn & Tavern, which has been owned and operated by three generations of her family. “My grandparents went on their first date here, and since then, the inn has become their legacy. We love showing off The Red Fox, with all of its quirks and its hundreds of years of history.” 

Many elements of the tavern have had long lives: The Tap Room served as a hospital during the Civil War, the bar is made out of reclaimed wood from a surgeon’s operating table, and an original  beam keeps watch over the door. “The goal is to maintain the integrity and history of the space while writing new chapters,” says Engle.  

Have A Memorable Meal

King Street Oyster Bar

Several downtown boutiques and restaurants, tucked snugly along Washington Street, open their doors to the cool air. King Street Oyster Bar features a selection of seafood and a row of tables lining the sidewalk, making it an ideal place for people-watching. 

Tremolo Bar And Knead Wine

One of the newer additions to the dining scene, Tremolo Bar serves small plates both indoors and  out on a light-dappled patio. The showstopper here is the flaming chorizo, which adds a touch of drama to dinner. Also from Jarad Slipp (the mind behind Tremolo), Knead Wine has set up shop just steps away and is a favorite for pick-up pizzas. Expect creative combinations like the Knopfler (with roasted  squash, maple-sage ricotta, toasted hazelnuts, and balsamic). As you’re checking out, grab a pack of Slipp’s enormous chocolate-and-peanut cookies at the register. 

Bluewater Cocina

This food truck, which has tacos, burritos, margaritas, and other Mexican specialties, has quickly become one of the buzziest eateries in town. It is parked behind Nature Composed, a garden shop teeming with greenery and design-minded gifts. Hidden in the back, Bluewater is small and unfussy with covered outdoor seating that’s surrounded by curtains of hanging vines and frequented by bumblebees flying among the tall stands of flowers. 

Shop One-Of-A-Kind Stores

Clothing And Home Goods

Notable retail options in the area include The Shaggy Ram, which sells a variety of elegant imports from England and France, and Tully Rector, a clothing store that has been open in Middleburg for more than 30 years. Crème de la Crème is popular for home goods and is stocked with an assortment of glassware, candles, linens, and garden accoutrements. 

Along South Madison Street, Federal & Black greets patrons with beautifully displayed gifts and furnishings. After relocating to Middleburg, Rebecca Kidder founded the shop in 2023 and curated an inventory that was inspired by Virginia, German, and Early American styles. 

Antiques And More

Thistlethwaite Americana purveys the finest 18th- through 20th-century pieces you’ll find in the region, while Middleburg Antique Gallery is stuffed with a wonderful collection of furniture, art, and jewelry. An open door here is an invitation to hours of browsing, and you’ll want to linger. The gallery smells faintly of cinnamon and polished wood. 

Books

Only a few doors away, Middleburg Books also opened in late 2023. The brainchild of friends and co-owners Mary Beth Morell and Christina Duffy, it is a jewel box for anyone who loves to read. A spangled starburst chandelier presides over the checkout desk and is surrounded by gold stars strewn across the midnight-navy ceiling. “We met as librarians in D.C. and were inspired to create a book-filled space where people can feel safe and seen,” says Duffy, gesturing to a gathering of customers trading stories at the till.

Although it hasn’t been open for decades—yet—Middleburg Books has already become a dynamic hub of activity for all kinds of readers. “We’ve received such a warm welcome from the community. There were 50 people at the ribbon cutting, and they weren’t our moms,” Morell says, laughing. “We’re grateful because so much growth can be traced to the Salamander Middleburg resort and the energy and visitors it has brought to the area. We wouldn’t be here without Sheila Johnson and the Salamander.” 

Book A Stay At The Salamander (Or Just Visit)

Take the winding drive to Salamander Middleburg, and you’ll soon feel any tension you may harbor melt away entirely. This place came to be in 2013 thanks to Johnson, an entrepreneur, philanthropist, and former television executive. Set on 340 acres, the property has a luxury spa that stretches across more than 23,000 square feet, trails for  hiking and biking, wide patios overlook- ing green lawns and old-growth forests, a catch-and-release fishing pond, and paddocks and stables that allow resort guests to bring and board their horses while traveling. 

The food and beverage options include Harrimans, with a menu that incorporates ingredients from local farmers, and Gold Cup Wine Bar, offering a variety of Virginia wines and seasonal cocktails. The latest addition here is a neighborhood called the Residences at Salamander, where those who have fallen in love with the region can buy a home and stay forever. 

Over the past decade, the Salamander has created spaces to appreciate the traditions of Loudoun County while bringing new businesses, tourists, and programming to the area, like the Middleburg Film Festival, held in October. 

Visit A Vineyard

You could say this town is in the heart of wine country, but to be more precise, it’s part of the Middleburg Virginia American Viticultural Area (AVA). Just about every drink menu you encounter basks in abundant local selections, from Cabernet Francs to blanc de blancs. Established in 2012, this AVA encompasses 30 wineries that make their homes in Loudoun and Fauquier Counties, and almost all of them have incredible views. 

Boxwood Winery

Must-see destinations include Boxwood, which was founded by John Kent Cooke, a former National Football League team president and owner. Take a tour through the workings of the property, and you’ll see a fascinating soil display that explores the concept of terroir and the ways the earth contributes to the development of wines. Tastings and events happen in a cool, barrel-lined cellar known as the Cave, while the best scenery can be found at the Pavilion, a high point where vines sprawl out all around. 

Cana Vineyards

Cana Vineyards has a two-story patio set along the hillside with verdant vistas of the grape-laden plants. Cana’s bright whites and earthy reds are the work of Melanie Natoli, the winemaker, vineyard manager, and 2022 winner of the Virginia Governor’s Cup. Rosés are among Natoli’s specialties, and one kind made with Cabernet Franc grapes won multiple gold medals in international competitions during 2023. Visitors are invited to sit in Cana’s tasting room, a structure with transparent walls that can be rolled up to let in  the breezes from the mountains. Settle in, and enjoy the repetition of swirling, pouring, and sipping. The splendors of autumn are waiting to be discovered here—both the small details and the sweeping views. 

More Wineries To See

At Greenhill Vineyards, which couldn’t be more aptly named, picnic tables are scattered across the grounds. Perched atop a bluff near the Bull Run Mountains is 50 West Vineyards.

No matter where you roam in and around Middleburg, the scenes are made by the glories of the landscape and also by the region’s many hands—those who tend the place and steward each of its chapters, leaving their marks, as well as those passing through who experience its wonders anew.