Flannel Shirt–Required Fall Getaways

Whether your goal is leaf-peeping, antique-browsing or straight-up R&R, there is a fall getaway destination with your name on it. And just as summer trips have their required packing list (bathing suit, cutoffs and not much else), so too do their autumnal counterparts.


The number one item in our weekend bags this season? The Flannel Tomboy Workshirt, a ridiculously cozy, oversized button-down, is basically made for any and all fall travel itineraries. Here, three destinations (complete with picks for where to stay, eat and have fun) we can’t wait to enjoy.


Stay: In one of the plush, colorful rooms at Pomegranate Inn.

Eat: Make a meal of locally caught bivalves at Eventide Oyster Co. and try the whoopie pies at Two Fat Cats Bakery. When you’re not actually eating, read about it; the selection at Rabelais Books is entirely food-focused.

Do: Take a short ferry ride to nearby Peaks Island where you can bike the scenic four-mile loop, then meander the streets of Old Port and catch a show or film at Space Gallery.


Stay: At the centrally located Union Street Guesthouse or, if you’re traveling with friends, splurge on Ten Broeck Cottage, a sprawling and stunning modernist house with acres of apple trees.

Eat: Revered New York City chef Zak Pelaccio recently pointed his compass due north to open Fish & Game, which boasts a menu highlighting locally sourced ingredients.

Do: Troll the myriad antique stores lining Warren Street and visit two very different estates: Olana, the one-time home of artist Frederic Erwin Church, and Hyde Park, the former residence of Franklin D. Roosevelt.


Stay: In one of 16 ocean-view yurts at Treebones Resort or one of the cozy modern-rustic rooms at Glen Oaks Big Sur. (Bonus: The Big Sur cabin has twin outdoor soaking tubs and a fire pit surrounded by the majestic redwoods.)

Eat: You can have breakfast, lunch and dinner at Big Sur Bakery & Restaurant, where the wood-fire oven figures big in a variety of dishes including a slew of pizzas (a morning variety is topped with bacon and eggs).

Do: Hike one of the many scenic trails at Point Lobos State Reserve, meditate and take a dip in the hot springs at Zen retreat Tassajara, then pay homage to one of literature’s greats with a visit to the Henry Miller Memorial Library.