Wildflower Farms, Auberge Resorts Collection

Hudson Valley, New York

Leaf peepers, assemble: Just 80 miles north of NYC, on 140 idyllic acres in the Hudson Valley, Wildflower Farms is where you go for sweeping views of the Shawangunk Ridge in all its autumnal glory. Settle into one of the freestanding cabins scattered across the property and you’ll have a dozen places to cozy up: by the fireplace, on your terrace, in your private garden… (Don’t let the word “cabin” throw you: These Electric Bowery–built cottages are intimate and woodsy but still well-appointed and comfortable.)

At the restaurant, chef Rob Lawson and the property’s founding farmers—who have a cooking school and farm education center on-site where you can learn to pick, pickle, and preserve—serve a New American menu based in pan-Asian techniques and seasonal, sustainable ingredients.

What to Pack: Opt for outdoorsy pieces in plush textures to echo the property’s laid-back-but-luxe vibe. Like a nostalgic cable-knit poncho or a mustard-hued wool sweater and wide-wale corduroys. A chic, chillproof puffer and shearling-covered boots will keep you warm on a nature walk or foraging excursion. And versatile accessories (classic shades, diamond studs) and nourishing skin care round out your assortment.

What to Bring

Villa mara

Carmel-by-the-Sea, California

The great secret of the California central coast is that fall is its best season: The crowds thin out, the skies brighten, and the fog clears. Which means you’re due for a trip up (or down) PCH for a weekend at the adults-only Villa Mara, just a skip from the beach in Carmel. It’s the kind of place where you’ll emerge through French doors onto your private patio in the morning and take your time getting to breakfast downstairs (expect quiche, pastries, and really good coffee).

Carmel’s beauty lies in its slow pace. Walk over to Mad Dogs & Englishmen and rent an electric bike—you’ll want to spend a leisurely morning cycling down 17-Mile Drive (we recommend using your lunch stop at The Links at Spanish Bay as a turnaround point). Meander down to the water and make eye contact with the Pacific Ocean for a few hours. And as the sun sets, how about a cocktail or a glass of red by Villa Mara’s firepits?

What to Pack: A stretchy navy-blue set and cushiony sneakers for strolling or biking, plus a snuggly sherpa jacket to keep you warm in the ocean breeze. Your formula for everywhere else? Easy, elevated pieces that match the California-coastal vibe—like wide-leg jeans, a chunky knit, and sleek ankle boots, with a sculptural leather crossbody to finish the look.

What to Bring

Hotel Grand Stark

Portland, Oregon

With Hotel Grand Stark, Palisociety captured the hipster flavor of Portland and omitted the kitsch—and the result is totally charming. It’s pretty enough to hang out in all day if you need to; like other Palisociety properties, it’s built with comfy common areas and a coworking space. But you’re not in downtown Portland to stay inside. Here’s what’s on the docket: You could spend a week thrifting and boutique-ing through town, or you can one-stop it at the expansive House of Vintage. Catch a car across town to Great Notion for supremely special beers you can only get here. (Even if you’re not usually into sours, we’re betting you’ll walk away with a case.) And for dinner, take your pick between citrusy, brothy noodles at Tokyo transplant Afuri Izakaya or Thai BBQ and tiki drinks at Eem.

What to Pack: Crisp black jeans, an ultrafine cotton-cashmere turtleneck, and toothy tread soles are equal parts cool and practical. You’re in the PNW, so don’t forget a warm snood and a hooded rain slicker. And in the (likely) event that you stumble upon colorful street art, a film camera is the most Portland way to document it. For dinner, swap the jeans for a structured mini, then add a cozy plaid shacket and a gleamy pinkie ring for a touch of polish.

What to Bring

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