The Loudoun County town known for its equestrian flair is a storybook setting in the fall. Cradle a warm drink as you walk quaint streets and browse shops, slip into wood-paneled taverns, and celebrate the season at local festivals.
Distance from DC: 45 miles
Where to Stay
In the heart of Middleburg, the Red Fox Inn & Tavern has 22 guest rooms, suites, and cottages. It’s also home to two of the town’s great eateries: the Tavern, a prix fixe dining room (where John F. Kennedy famously held a press conference), and the Night Fox Pub. For a more secluded getaway, Goodstone Inn is a nine-minute drive from downtown and features 18 luxurious rooms and suites across six historic buildings. Some suites are outfitted with claw-foot tubs, while the cottages have fireplaces. The picturesque property spans 265 acres, much of which is dedicated to sustainable practices, such as a farm with chickens, sheep, cattle, and vegetables for farm-to-table cuisine. You can even pay a visit to Greyson the llama, the inn’s unofficial mascot.
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Things to Do
Stroll the charming brick streets while popping into shops. Every Little Something is a beautiful stationery-and-paper-goods store with a rainbow of notebooks and pens plus other cute items such as children’s plushies and glass cocktail stirrers. Find cheeky gifts at Brick & Mortar Mercantile, stocked with clothing, candles, and trinkets, many American-made. At indie Middleburg Books, readers can peruse the floor-to-ceiling collection of novels and cookbooks. For vintage wares, Middleburg Antique Gallery has a trove of local, European, and stateside antiques from more than 45 dealers; nearby, explore three floors of retro finds at the Accidental Peacock thrift shop. Meanwhile, the home-goods store Crème de la Crème may inspire you to overhaul your china cabinet with new tableware. Need a massage after hauling shopping bags? Unwind with a spa treatment at the luxe Salamander Middleburg.
The town’s calendar is also packed with fun seasonal events. Channel Munich in Middleburg during Oktoberfest on September 20, showcasing German food, biergartens, music, and games. On October 11, immerse yourself in horse country’s steeplechase history at the Virginia Fall Races, when 10,000 fans gather at Glenwood Park.
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Dine and Drink
Start your day with a latte at Middleburg Common Grounds, a warm cafe with coffee, tea, pastries, and sandwiches. There’s indoor and outdoor seating as well as treats for dogs. At lunchtime, Red Horse Tavern offers American cuisine under patio umbrellas. Want to take in the surroundings while enjoying a local brew? Celebrate the apple harvest at Mt. Defiance Cidery & Distillery or grab a pint at Lost Barrel Brewing, located on a horse farm. Both are dog-friendly and host live music.
This article appears in the September 2025 issue of Washingtonian.
