Annapolis, Maryland
Distance from DC: About 1 hour
If you love polished prep, all things Americana, and crabs on the waterfront, head to Maryland’s quaint capital. The shops here veer mostly classically chic (yes, there’s lots of Lilly Pulitzer) and maritime antiques, but there are some pretty darn trendy places, as well. Don’t miss: Re-Sails for sleek sailing duffels, in-business-since-forever Laurance Clothing for classic boating garb for your guy, and the handbag line Hobo’s amazing flagship store, which just opened in April.
See our Annapolis shopping guide.
Leesburg, Virginia
Distance from DC: Less than an hour
With plenty of Anthro-chic antique and homegoods stores, plus one of our favorite coffee shops in NOVA, this somewhat sleepy historic town is ideal for a less rowdy group that wants to spend a few hours away from the noise of the city. Don’t miss: The Out With the Girls category in our Great Day Trips highlights our favorite shops in Leesburg.
See our complete Leesburg shopping guide.
Charlottesville, Virginia
Distance from DC: About 2.5 hours
This might seem like a long drive, but the trip south down 29 is so gorgeous you won’t mind. And there’s plenty to do in this college town besides tailgate at the football stadium and continue to party on the Corner. Head to the more grown-up, brick-lined downtown, where restaurant seating spills onto the sidewalk and boutique shopping is way more forward-thinking than you’d ever expect. Make a weekend out of it with a trip to nearby vineyard. Don’t miss: Anthrolopogie fans will flip for Eloise and Roxie Daisy; Sustain is one of the most gorgeous eco-boutiques we’ve ever laid eyes on.
See our complete Charlottesville shopping guide.
Frederick, Maryland
Distance from DC: About 1 hour
Where else in Maryland can you dine at a Top Chef winner’s restaurant, rummage through a 55,000-square-foot antiques emporium, and find Bloomingdale’s-worthy brands in cozy boutiques? If you think of an answer other than Frederick, let us know. Seriously. For stunning views of rolling countryside, take 15 North instead of 270 into town. Don’t Miss: Silk & Burlap is a slice of big-city sophistication in clothing and home decor, and Urban Cottage stocks beautifully packaged bath and beauty products.
See our complete guide to Frederick.
Richmond, Virginia
Distance from DC: About 2.5 hours
There’s something a little grittier about Virginia’s capital city, and we love it for exactly that reason. Between the amazing brunch at Lulu’s, custom burgers at Station 2, and the bevy of boutiques in Carytown (not to mention excellent hipster street style around the VCU campus), there’s plenty to entertain all your senses. Don’t miss: Need Supply is our honest-to-god favorite boutique on the East Coast; the Shops at 5807 house 21 different shops inside one storefront.
Check out this great Design Sponge post for a more complete list of shops to explore.