Where: Philadelphia, Pennsylvania
What to do: History buffs already know Philly is the place to nerd out over early American artifacts, but there's also the top-notch boutiques of Rittenhouse Square, under-the-radar music venues like The Barbary, and incredible artsy destinations like the Rodin Museum and the Philadelphia Museum of Art, where you can catch special exhibitions on architect Zaha Hadid, photographer Zoe Strauss, and Van Gogh. Our picks? Shop for colorful housewares, bedding, and gifts at Open House near City Hall, then break for a cheesesteak.
What to wear: A comfy sweater and cropped trousers are ideal for a day of boutique browsing and museum-hopping, and flat oxfords will prep you for a day on your feet. A colorful crossbody bag and chic sunnies are the perfect casual-cool finishing touches.
Mango Navajo Style Jumper, $39.99, available at Mango; J.Crew Baby Brompton, $158, available at J.Crew; Bauble Bar Chroma Craft Wraps, $28, available at Bauble Bar; Super Lucia Sunglasses, $163, available at Piperlime; MHL by Margaret Howell Cropped Cotton-Twill Straight-Leg Pants, $295, available at Net-a-Porter; DV by Dolce Vita Mini Oxford, $78.95, available at Endless.
Photo: Via Greater Philadelphia Tourism Marketing Corporation
Where: Richmond, Virginia
What to do: Mixing Southern charm with the energy of a college town and plenty of old-school attractions, Richmond is one of our fave spots for unearthing treasures old and new. Hit up Carytown for adorable boutiques, take a stroll down Monument Avenue, or plan your trip around one of the city's wine festivals to taste some of the region's best vintages. We suggest taking a walk through Lewis Ginter Botanical Garden, then checking out the shops on Cary Street (especially Need Supply, our favorite), before settling in for a cozy dinner at Can Can Brasserie.
What to wear: A simple dress and walkable ankle boots can take you from strolling between shops to a casual dinner, and a roomy tote will let you stash everything from a bottle of wine to your great new jewelry finds.
Melissa Odabash Jamie Striped Stretch-Jersey Mini Dress, $230, available at Net-a-Porter; 3.1 Phillip Lim Camp Jacket, $650, available at La Garconne; Rag & Bone Mid Moto Boots, $535, available at ShopBop; H&M Necklace, $17.95, available at H&M; Zara Shopper with Clasp Frame, $99.90, available at Zara.
Photo: Via Richmond Metropolitan Convention & Visitors Bureau
Where: Lewisburg, West Virginia
What to do: Feeling outdoorsy? Head to wild and wonderful West Virginia for plenty of adrenaline-pumping fun — we're talking treetop tours, zipline adventures, rock climbing, whitewater rafting, hiking, mountain biking, and more. Make the quaint little town of Lewisburg your home base, and spend your long weekend getting back to nature, hunting for antiques, or browsing some of the best farmers' markets around. The perfect itinerary? Spend the morning on the trail in one of the area's state parks or navigating rope bridges and ziplines on a treetop tour. Then, decompress at The Greenbrier's acclaimed mineral spa.
What to wear: Comfort is key on a relaxed getaway like this one, so opt for broken-in chinos, a loose-fitting tank and windbreaker, and flat boots you can wear all day. Stash the day's necessities in a practical (but still really cute) backpack.
H&M Chinos, $29.95, available at H&M; Baggu Backpack, $34, available at Baggu; Kain Classic Modal and Silk-Blend Tank, $85, available at Net-a-Porter; TopShop Textured Drawstring Windbreaker, $56, available at TopShop; ONE by Matisse Footwear Oscar Ankle Booties, $188, available at ShopBop.
Photo: Courtesy of Southern West Virginia Convention & Visitors Bureau/Steve Shaluta