4 Fall Weekend Itineraries—and What to Wear for Each
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It’s easy to fetishize fall: There’s that crisp in the air, the blaze of changing leaves, the pumpkin-dotted doorsteps, the steam rising off a mug of hot cider. And yet peak fall is all too brief—a fleeting moment suspended in time before the sprint to the holidays begins. To help you make the most of it, we’ve mapped out four weekend itineraries—and a sartorial plan to go with each one.
Courtesy of Airbnb/The Six Bells Countryside Inn
The Hudson Valley
Head upriver from the city and make a stop at Storm King before checking in to the Six Bells Countryside Inn, Audrey Gelman’s storybook-perfect 11-room hideaway. On the agenda for the weekend: thrifting in Rosendale (Club House Vintage), antiquing in Rhinebeck (Beekman Arms, Rhinebeck Antique Emporium), a stop at Samuel’s Sweet Shop, and at least one meal at the Feathers Tavern, where you will absolutely want to order the short rib and potato croquette. The dress code for the weekend’s adventures: countryside chic. Think good denim, sturdy brown boots, and hits of deep red. A cropped jacket and a burgundy beanie give the classics a current feel, while the diamond drops and signet ring lend an elevated counterpoint to the more rugged pieces.
New York City
There are so many (perfect) ways to do autumn in the city, but the one topping our list right now is Upper East Side–centric (because the Central Park Mall when the leaves on the elms change? My god). Start with a cappuccino and oven-baked eggs at Via Quadronno, then head into the park and wander for a bit before walking north through the Ramble to the Met. The permanent collection never disappoints, but the Orientalism exhibit currently on view is a standout. Afterward, pop over to the just-reopened Café Sabarsky at the Neue Galerie, order a hot chocolate and a punschkrapfen, and thank us later. As for the lookbook: It’s classic NYC—black on black on black, punched up with accessories that add texture, tension, and personality. The patterned scarf breaks up the streamlined silhouette, while the antique French Art Deco coral-and-onyx ring becomes a focal point, bringing a graphic hit of color and a collected, artful quality that feels especially fitting for the day’s activities.
Courtesy of the author
The North Fork
A fall weekend by the water is hard to beat. And on the North Fork, this time of year is particularly sweet: The crowds thin out, but all the charm remains—in fact, it’s arguably amplified as the leaves change and the grapevines shift from green to burnished gold. Check in to the Menhaden in Greenport—it’s central and comfortable. Nonnegotiables: A lazy afternoon at Croteaux Vineyards, a stop at Mattituck Mushrooms, self-serve oysters from Little Ram, and dinner at First & South.
As for what’s in your weekender? A marinière is a must; wear it with creamy denim, tortoiseshell shades, and sleek gold extras. For day two, a swishy skirt in painterly plaid paired with a chunky mockneck and knee-high boots makes for a polished, seasonal take on coastal chic. And the blue suede tote adds an unexpected tonal shift to both looks.
The Connecticut Shoreline
Across the Sound from the North Fork, Mystic has a similar coastal appeal coupled with small-town New England charm. Check in to the Whaler’s Inn on Main Street, then spend a few hours strolling and shopping. Stop at Sift for the best chocolate chip cookie you’ve ever had, hit up Oyster Club for happy hour, then do dinner at the Shipwright’s Daughter (the tasting menu is our rec, but if you go à la carte, don’t miss the Rohan duck with pickled blackberries and chili crisp). On Sunday, grab a coffee and set south early to make it New Haven in time for the crypt tour at Central Church on the Green: The 137 gravestones are a beautifully preserved example of early Puritan funerary art. Then pick up a pie at Sally’s before heading home.
As for the outfitting, a collegiate approach feels fitting here: Cropped charcoal trousers and polished flat boots create a clean foundation that’s softened by an ivory tank and a pale-pink cardigan. A structured bag brings a classic, ladylike element, while the cropped jacket and knit beanie keep the overall look relaxed and modern.
