3 Fall Weekend Getaways and What to Wear

Here, three destinations topping our weekend-away wish list at the moment—along with a carry-on-friendly edit for each one. The linchpin for all three packing lists: a pair of sneakers as good-looking as they are comfortable. Like the New Balance 9060s. The fashion-forward design, with its chunky sole and distinctive silhouette, is versatile—easy to wear with streetwear and workout clothes alike.

THE WESTON

WESTON, VERMONT

There’s nothing quite like New England in leaf season, and Vermont is the epicenter of all the beauty. This eight-room gem of an inn makes a luxurious home base for a weekend of taking it in. Each room is unique, decorated (exquisitely) with antique furniture and artwork, William Morris wallpapers, and plush upholstery in rich, deeply saturated hues. There are a spa and gym on site, along with a restaurant, the Left Bank (it’s excellent—order the deviled eggs topped with mustard seed pearls) and a firepit to gather around in the evenings. During the day, there’s great hiking nearby (some challenging trails, some easier), antique stores to browse, and just on the other end of Main Street from the inn, the original Vermont Country Store, which sells everything from shampoo to hunting gear, table linens to bat houses—you’ll want to set aside a couple of hours to do it justice.

What to pack: Lean into the cozy vibes with textural pairings in a moody palette—a cashmere-blend cardigan over a fluid silk maxiskirt, say, or a crisp cotton-poplin top tucked into plush corduroy trousers. A comfortable set to curl up by the firepit in. And to pull it all together, some streamlined outfit-finishers—bag, boots, sneakers—in a jet-black palette.

ZERO GEORGE

CHARLESTON, SOUTH CAROLINA

With 16 rooms in five historic (and beautifully restored) buildings set around a lush courtyard, this charming boutique hotel feels like your own personal bolt-hole in downtown Charleston. Inside, the décor is elegant and understated, with a sort of French-country-meets-Lowcountry aesthetic. There’s a fine-dining restaurant as well as a caviar bar on-site. When you’re ready to venture out—on foot or on one of the complimentary bikes—some ideas: Head over to walk the Battery. Or make your way toward King Street to browse the shops (HART is a favorite for jewelry, and it’s right next to Wynsum Antiques, a can’t-miss). For lunch, Leon’s for oysters, fried chicken, and hush puppies. And in the evening, a glass of Gamay at Graft followed by dinner at the intimate Chez Nous (the menu, which changes daily, is posted on Instagram each morning). Last but not least, set aside a few hours for a visit to the International African American Museum, which just opened last year.

What to pack: You’ll want light, easy pieces that feel feminine but not twee, like a sweet-meets-cool sundress in palest yellow and a simple tennis dress you can wear for workouts or walkabouts (with a sweater draped over your shoulders). A ruffled top in black-and-white checks paired with tailored shorts is laid-back enough for daytime and polished enough to wear straight to dinner.

ALISAL RANCH

SANTA YNEZ VALLEY, CALIFORNIA

Set on 10,500 acres in Santa Barbara wine country, Alisal Ranch is all about embracing the great wide open. Spend an afternoon horseback riding in the surrounding hills, take a canoe or a paddleboard out on the lake, hit the trails on a mountain bike or your own two feet, or just set up camp on a lounger by the pool. The rooms are comfortable and well-appointed, with a Western bent—think stone fireplaces, exposed wood beams, woven textiles, and vintage photographs of the ranch in earlier times (its history goes back to 1810). With all it has to offer on site, it is a more immersive escape than the other two, but there are still spots worth leaving the property for: You could head into nearby Solvang for a tasting at Blackjack Ranch Vineyards, followed by a steak dinner at Coast Range. A slightly longer drive will take you to Los Olivos, where you can’t go wrong with a meal at Bar Le Côte (try the aged branzino with romesco) or Mattei’s Tavern (the crispy cauliflower with roasted garlic tahini and spiced honey is a standout).

What to pack: If this weekend had an invitation, the dress code would be rustic chic—say, dark blue denim with a cherry-red sweater, cowboy boots, and a diamond-encrusted horseshoe pendant. A knit cotton cardigan-and-skirt set in dark espresso brown is a sleek (and low-key sexy) choice for dinner.