Why we're packing our bags: Dealers and the country's leading designers convene in tents, barns, and dusty saloons to create flea-market nirvana—a shopper's wonderland—at the fabled Antiques Week (September 21-October 7, roundtop.org).
Perfect for: Anyone whose heart races with the thrill of finding treasure at a roadside antiques stand.
On the itinerary: Aim to kick back and get lost, drifting through the town's quaint shops (such as the vintage boutique Junk Gypsy (gypsyville.com)), cafes, galleries, and watering holes. Roll down the highway a few miles to tiny Warrenton for its sea of vendors.
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Save room for: The justifiably famous cherry or coconut chess pie at Royers Round Top Cafe (royerscafe.com).
Rest your head: The Prairie by Rachel Ashwell (theprairiebyrachelashwell.com), the Shabby Chic designer's bed-and-breakfast, sells out fast. (Rates from $245.) For other options, check out the lovely restored cottages and guest rooms at Round Top Inn. (Rates from $85, roundtopinn.com)
Bring it back: The polka-dot Dorset towels ($36 each) from Shabby Chic Couture (rachelashwellshabbychiccouture.com), Rachel Ashwell's new shop, or vintage hotel key chains ($7) from Junk Gypsy. Buy both the Thelma and Louise models, and give one to your favorite partner in crime.
Don't miss: The rowdy Junk-o-Rama Prom on October 4. The event (described as "a second life for old prom dresses") draws revelers in tiaras and scuffed up boots from around the U.S. (Yes, that's Miranda Lambert twirling by the bar.)