Middleburg has a history of welcoming visitors. Thirty-seven years before the town was founded, an 18-year-old surveyor named George Washington came to map the area and to visit with relatives at what today is the Red Fox Inn. A tavern has stood in that spot since 1728.

Virginia statesman Levin Powell founded Middleburg in 1787, when he bought 50 acres, at $2.50 an acre, from one of Washington’s cousins. Powell named the town Middleburg because it sat midway between Alexandria and Winchester, each a day’s ride away on Ashby Gap Road, now Route 50. Middleburg was a rest stop.

The location on a trading route helped the town prosper until the Civil War, when Union and Confederate armies alternately occupied the area and carried off crops and horses. The town served as a base for one of the war’s most colorful figures, Colonel John Singleton Mosby, the “Gray Ghost,” who staged guerrilla raids on Union troops.

By the early 20th century, Middleburg was a hub for fox hunting and steeplechase races. Still, it remained a relatively sleepy place until the 1960s, when visitors and residents such as John and Jackie Kennedy, Elizabeth Taylor, and Paul Mellon put the city on the map.

Washington Street, the main thoroughfare, has retained its charm despite traffic that can get heavy, particularly during the summer. There are many restaurants, antiques shops, art galleries, and stores selling clothing, gifts, wine, and books. Because so many of the buildings date to the late 18th and early 19th centuries, Middleburg is a pretty walking town. Start at the visitors center, known as the “pink box,” on North Madison Street for maps and enlightenment.

Just outside town you also can see some lovely scenery. Wine lovers can visit a number of vineyards, including Swedenburg Winery, a mile east of town. Swedenburg’s wines are quite good, especially the Riesling, and there are daily tastings and tours. Five miles east of town is Aldie Mill, a working gristmill that dates from 1809 and is open for tours.

Pizza to Peanut Soup

Finding a good place to eat in Middleburg is easy.

On the elegant end is the French Hound (101 S. Madison St.; 540-687-3018; thefrenchhound.com), which serves excellent food in an upscale setting. The best choices on a recent visit were seafood—a purée of white beans with fresh white anchovies on pizza and a grilled-salmon dish were superb—but meat and fowl are not far behind. Desserts are also very good. Most main courses are in the low to mid $20s; the wine list starts at $20. Chef John-Gustin Birkitt is from Leesburg but worked in France and the Napa Valley.

If you’re looking for local color, the Red Fox Inn (2 E. Washington St.; 540-687-6301; redfox.com) is the place. It is an institution in these parts. Try one of the daily specials, but include the peanut soup in any meal. The eggs Benedict and the crab cakes have their fans, too. Entrées average about $30.

Salvia Ristorante Italiano (3 W. Washington St.; 540-687-8711; salviaristorante.com) is straightforward northern Italian. Pasta is a good bet, but the kitchen can handle a nice range, from veal piccata to pizza. Main courses average $20.

For 1950s-style dining, complete with a counter as well as tables, go to the Coach Stop (9 E. Washington St.; 540-687-5515; coachstop.com), which offers a variety of standard American dishes for breakfast, lunch, and dinner. It’s a family-style restaurant in the best sense. Main courses average about $19.

For simpler fare in simpler settings, the choice is larger. Back Street Cafe (4 E. Federal St.; 540-687-3122) does a fine job with pasta and thick sandwiches. The Upper Crust (2 N. Pendleton St.; 540-687-5666), a bakery and restaurant, offers sandwiches on excellent house-made bread, plus house-made soups, pastries, and pies. For a good hamburger or sandwich, indoors or out, try Dank’s Deli (2 N. Liberty St.; 540-687-3456).

Red Horse Tavern (112 W. Washington St.; 540-687-6443) serves such staples as chili and meatloaf in a low-ceilinged room with red walls and a flat-screen TV. If it’s pizza you’re after, head for Teddy’s Pizza (7 E. Federal St.; 540-687-8880), which serves thin-crust pies in a downscale setting.

The town supports two ice-cream parlors. Scruffy’s (6 W. Washington St.; 540-687-3766) serves large scoops of Hershey’s, while Middleburg Creamery & Country Store (5 W. Washington St.; 540-687-4754), across the street, offers good house-made flavors.

To experience an old-fashioned soda fountain, head to Home Farm Store (1 E. Washington St.; 540-687-8882; homefarmstore.com) and walk up the stairs in the back. Or check out the market itself, which offers takeout as well as fresh meats, vegetables, and other food you can bring home. Everything looks as good as it tastes.

You’ll find more gourmet prepared foods, and a large wine selection, at Sheila Johnson’s Market Salamander (200 W. Washington St.; 540-687-8011; marketsalamander.com). Your choice: Pack up the fare for a picnic elsewhere or eat at tables on the property.