Film screenings out east, vintage cars in Newport, and a few good reasons to stay the night. Here’s where we’re going this October and what we’re packing.

Once Fashion Week is over, New York settles into a different kind of calendar. The coats come out, weekends open up, and suddenly a reservation two hours from the city sounds better than another Saturday at home.

October has plenty to plan around: a film festival in the Hamptons, antiques and cocktails in Hudson, a few nights in the mountains, and Newport at its most dramatic. Here are four getaways we’d make room for, with a daytime look and a dinner look for each.

SAG HARBOR  
Main Street, the Movies and Dinner by the Harbor

The Hamptons International Film Festival runs October 2–12, and Sag Harbor Cinema is one of its screening venues. Choose a film before you go. Spend the afternoon on Main Street, then head to the cinema and dinner afterward.

For the day: The Flavia Barong Mini in Cioccolato Brown, tall boots, and the Avignon Convertible™️ Drop Earrings as floral studs.

For the evening: Change into the Quinn Midi in Lapis Blue and attach the Avignon pearl drops. The dupioni gives a film-and-dinner night enough polish without turning it into a premiere look.

Stay at Faraway Sag Harbor and make breakfast by the water part of the plan.

HUDSON  
A Good Antique Find and a Better Cocktail

Start on Warren Street with no particular shopping list. There are enough antiques, galleries, and small shops to fill the afternoon. For cocktails, go to The Maker’s Lounge, set in a former carriage house, then stay for dinner in town.

For the day: The Sadie Top and Blake Crop Pant in navy. The matching separates look considered but leave you free to spend the day walking.

For the evening: The Soma Duo Bow Mini in Eventide Gardens, sheer tights, and a low heel. The print and shoulder ties are enough detail.

Check into The Maker if you want to pick up where you left off on Warren Street the next morning.

THE CATSKILLS  
A Cabin at INNESS

At INNESS in Accord, keep the schedule light. Arrive early enough to spend time on the property, then meet for dinner at the restaurant. The cabins, mountain views, and a reservation are plenty for one weekend.

For the day: The Dinty Off-Shoulder Top and Friday Pant in Morning Gingham is the cocktail outfit that feels at home in the Catskills.

For the evening: The Gabriella Midi in Twilight Marble with heels and a statement clutch. Its long sleeves and stretch jersey make sense for a comfortable but upscale dinning expereince.

Staying two nights? Pack the reversible Este Convertible™️ Jacket for another afternoon, worn over a plain tee and trousers so the jacket’s print stands on its own.

NEWPORT  
The Mansions and a Proper Dinner

Newport is good in October: the coast is cooler, the mansions are still there to explore, and dinner is worth changing for. If your trip falls October 1–4, add Audrain Concours & Motor Week to the itinerary.

For the day: The Isabel Short Sleeve Cardigan & The Demi Midi Skirt with flats and a coat. Wear the Carlotta Convertible™️ Earrings as simple gold flower studs.

For the evening: Change into the Casablanca Midi in Venetian Patchwork for dinner at Castle Hill Inn. 

THE ONE THING EVERY SUITCASE NEEDS

The daytime look has a plan. The dinner look has a reservation. The Gigi Pajama Set is for the part of the weekend you leave open: coffee in the room, a slow start, and the pleasure of staying a little longer.

Four places to go. A few good reasons to get dressed. Find your next weekend look among Mestiza’s Fall arrivals.

From the Stylist’s Desk