Steeped in history, the quaint hamlets that connect southern Maryland and Northern Virginia offer treasures that have been around almost 200 years–creating an antique lover's paradise.

Chartreuse & co.
At Chartreuse & co., you'll find historical treasures spread out across three barns.
| Credit: Robbie Caponetto

Antiquing Day 1: New Market, MD, to Paris, VA (67 miles): Start on the Old National Pike (Route 144) in New Market. Once known as "the antique capital of Maryland," the town has been a stopover on the historic National Road since its inception as a trade route in the late 1700s. Its stately, Colonial Main Street is lined with colorful antiques stores like 1812 House (48 West Main Street; 301/865-3040) and Robert Esterly Antiques (20 West Main Street; 301/865-8000), which specializes in custom-made furniture and restoring antiques. Then head west through the rolling hills and abundant farmland of Frederick County, and pull into downtown Frederick to shop for your dream tea service at Emporium Antiques (112 East Patrick Street; 301/662-7099), which sells silver, furniture, antique glassware, and more.

Leaving Frederick, motor south on State 85 for a few miles to Buckeystown, where you'll find Chartreuse & co. (301/874-1882), a group of tucked-away farm buildings that host tag sales the third weekend (Friday-Sunday) of each month. Chartreuse is owned by Virginia Crum, who dreamed up the idea that her family's homestead could become a design destination. Her shop now fills three barns, features 20 vendors, and welcomes roughly 2,000 visitors during sale weekends. Inside, one barn houses a European boutique where crystal chandeliers dangle over a vintage red velvet-and-gilt French love seat and Tuscan trestle tables display ironstone platters.

From Buckeystown, head west about 11 miles, turn south on U.S. 15, cross the Potomac River, and stop for lunch and more antique shopping in Leesburg, Virginia. Warm up with Lightfoot Spicy Creamy Tomato Soup and Honey Ham Biscuits with Smoked Virginia Ham at Lightfoot Restaurant (11 North King Street; 703/771-2233), a soaring space that used to be an old bank. Afterwards, walk the same paths (now brick sidewalks) that General George Washington once strolled to the Leesburg Antique Emporium (32 South King Street; 703/777-3553) to admire furniture, linens, old books, jewelry, and various architectural items selected by more than 55 dealers.

Continue on U.S. 15 to Middleburg, in the heart of Virginia's hunt and wine country. Stop for a drink at The Red Fox Inn and Tavern (2 East Washington Street; 540/687-6301), the oldest continually operating inn in the United States. The basement taproom once served as a hospital for Confederate soldiers, and the bartender just might save your life with a Hendricks and Tonic adorned with a spear of cucumber. Once fortified, amble along Washington Street to some of the finest antiques stores in Virginia, including Hastening Antiques (7 East Washington Street; 540/687-5664), JML French Antiques (17 East Washington Street; 540/687-6323), and Middleburg Antique Emporium (107 West Washington Street; 540/687-8680), a multi-dealer store specializing in fine antiques; English, American, and French furniture; sterling; regal clocks; fine porcelains; linens; paintings; and more. Follow the fragrance of freshly baked pastries (and the prospect of chocolate chip cookies to go) to Home Farm Store (1 East Washington Street; 540/687-8882), a stylish market selling the region's best artisanal cheeses, perfect produce, and heirloom meats, among other temptations.

For dinner, hoof it around the corner to The French Hound (101 South Madison Street; 540/687-3018) and join the locals at the small cafe tables in the bar to make a meal of appetizers—French breakfast radishes and sea salt, Saucissons et Cornichons (dried French salami with strong little pickles), perfect golden frites dusted with fresh herbs, and a glass or two of Cotes du Rhone. As the light fades, follow U.S. 50 westward to Paris (Virginia, that is) and check in to The Ashby Inn & Restaurant (692 Federal Street; 540/592-3900). The building was established in 1829, and the inn, opened in 1984, overlooks lovely grounds that stretch to the rolling hills of Sky Meadows State Park. Don't forget the extra quilt in the antique hutch—November nights can get cold here.

Antiquing Day 2: Paris, VA, to Upperville, VA (5 miles): Fresh-squeezed orange juice, anyone? Ashby Inn owners Star and Neal Wavra moved to Virginia from the famed Blackberry Farm in Tennessee a few years ago, created a killer wine list (Neal is a sommelier), and worked with chef Tarver King to foster relationships with area farmers. Sample the winning results of their experience (and new neighbors) with breakfasts such as omelets with local morels and sweet butter from a nearby dairy and a Croque Madame made with spice-scented brioche French toast, Speck, Gruyère, a fried egg, and potatoes.

After one more cup of coffee, walk across the street and meet Carol and Gary Konkel, owners of American in Paris (694 Federal Street; 540/592-9008), which specializes in American country-and-folk art, including stunning baskets, quilts from the early 1900s, and maple candle stands. From Paris, follow U.S. 50 a few miles east to the village of Upperville—it's as pretty as a stage set—and visit Matthews House and Garden (9160 John S. Mosby Highway; 540/592-7147), a stunning interior design-and-home store housed in a 186-year-old church.

For a final dose of history, stop for lunch at Hunter's Head Tavern (9048 John S. Mosby Highway; 540/592-9020), an English pub that serves organic farm meats and produce from neighboring Ayrshire Farm. Grab a seat near the fireplace, sip a pint of local ale, and dig in to moist, fragrant baked chicken with mashed potatoes and seasonal vegetables. You'll need the fuel for all the shops left to hit on the way home.