The Insta-Worthy Places to Visit in October

Where to Stay

Set amongst the Blue Ridge mountains, the Inn at Willow Grove is an ideal fall destination for travelers looking to escape, while still craving the comforts of home. Book one of the boutique rooms in the colonial-style Manor house that dates back to 1778, or stay in one of the private cottages peppered across the beautifully-manicured, 40-acre property. Each room is uniquely decorated and comes equipped with a fireplace, spacious private porch, and deep soaking tub. Spend warmer fall days lounging by the heated saltwater pool or relax around the outdoor fire pits on chilly fall evenings. When you wake up each morning, French-pressed coffee and house-made beignets will be delivered to your door.

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What to Do

If you can pull yourself away from the inn, explore the winery at the 18th century Barboursville Vineyards. Sip on a glass of cabernet franc in the library-slash-tasting room with a view overlooking the grape vines, then explore the historic ruins located on the property, built by none other than Thomas Jefferson. For added culture, carve out time to visit James Madison’s home at Montpelier, where he wrote much of the U.S. Constitution, just a few miles away.

Where to Eat and Drink

Head back to the inn for dinner at Vintage Restaurant & Pub, open exclusively to inn guests. Order the vintage lump crab cake with avocado puree, daikon summer salad, and peach & pepper gel to start, then try the spice rubbed monkfish with Spanish couscous and olives or the filet mignon served with charred onions, zucchini, and a bacon-chili jam for the main course.

Where to Stay

We've written about Lewes as a great, less-crowded beach destination in close proximity to New York City, and The Dog Fish Inn's fall offerings don't disappoint either. Its new outdoor activity package makes it easy to explore all the area has to offer.

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What to Do

Upon checking into the inn (we recommend booking the 1,200-square-foot Super Sweet!), the front desk will equip you with a slew of fall adventure guides and access to gear stored in their on-site shed (think: beach cruisers, hiking gear, hammocks, and binoculars). No adventure is off-limits, and the shed is constantly updated with new supplies throughout the season.

Where to Eat and Drink

Spend your days out in nature but be sure to return in time for happy hour—best spent sipping on one of Dog Fish brewery's seasonal pumpkin ales. For dinner, stroll the streets of the quaint downtown area of Lewes before making your way to Striper Bites nautical bistro. Order a crab bisque or baked oysters as a starter. For mains, you can't go wrong with one of their signature seafood dishes. Alternatively, make a reservation to visit Dogfish Head's brew pub.

Where to Stay

Set on the Snake River Valley with views of the Grand Teton mountain range, Jackson Hole’s Amangani resort is the ideal place to unwind or celebrate a special occasion this fall. Stay in roomy suites that have floor-to-ceiling views of the surrounding mountains, and zen interiors that incorporate natural elements, like wood and stone. Step out onto your private terrace for panoramic mountain views.

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What to Do

Outdoor lovers can fill their days exploring the autumnal scenery at nearby Yellowstone or Grand Teton National Parks. Participate in a private wildlife safari, hiking adventure, or elk tour coordinated by the resort. Back at home base, you can float amongst nature in Amangani’s all-season heated outdoor swimming pool.

Where to Eat and Drink

For breakfast, lunch, and dinner, the on-site restaurant offers local, sustainably-sourced meats, fresh fish, and in-season farm-to-table produce. If you’re visiting in celebration of a milestone, consider a custom dining experience like a chef’s tasting menu or a picnic in the forest.

Where to Stay

Book the White Barn Inn, part of the Auberge Resorts Collection, located in the charming coastal town of Kennebunk. With a recent update spearheaded by Jenny Wolf Interiors, the landmark property has a fresh new look that pays tribute to the inn's traditional New England aesthetic. Whether you choose a guest room, cottage, or suite, all have personal touches like fresh daily flowers and gorgeous views of the Kennebunk River.

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What to Do

Take part in a socially-distanced apple orchard excursion, or a private wine-and-cheese-pairing class set in the inn’s wine cellar. Make sure to carve out time for a beach walk to catch the fall sunset!

Where to Eat and Drink

For a quintessential New England weekend lunch or dinner, head over to The Clam Shack (open Friday to Sunday) for fresh seafood and local lobster dishes. Eat al fresco at picnic tables with waterfront views. For a more upscale dinner experience, book a table at the White Barn Inn Restaurant, where the chef highlights local Maine ingredients from nearby farms and fisheries.

Where to Stay

In a tiny cabin! With locations scattered across 11 U.S. areas, all of Getaway's accommodations are surrounded entirely by nature, built to provide a place for visitors to unwind and unplug. Ideal for an October escape, Getaway's tiny cabins in upstate New York have a thoughtful, minimalistic design that includes everything travelers may need to get the most out of their stay.

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What to Do

Spend your days hiking and exploring the area surrounding your cabin and return to the grounds for a cozy fall evening around the campfire. Getaway's tiny houses include cards and activity books for some analog ways to stay entertained.

Where to Eat and Drink

Flex your cooking muscles in your cabin, which comes equipped with a two-burner stove or the option to grill out over the fire. Need pots and pans? Getaway's got you covered with all of the cooking essentials. Non-perishables like coffee and pasta are for sale if you've left your essentials back at home.

Where to Stay

Set on 110 acres, The Blantyre, located in the Berkshires region, is all about foliage. The 1900s Tudor-style mansion is elegantly decorated with luxe fabrics and multiple fireplaces for warming up chilly October days. While The Blantyre has 24 rooms total, only half will be open for booking this fall—giving the estate an exclusive feel.

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What to Do

You don't have to leave the property to bask in prime leaf-peeping, but the surrounding landscape has a variety of fall hiking trails and waterfalls to explore. For a special occasion, book a hot air balloon ride for an incredible view of the autumnal colors. For a bit of culture, visit Chesterwood's outdoor sculpture gardens, or take a trip to the home of American abstract artists George L.K. Morris and Suzy Frelinghuysen.

Where to Eat and Drink

For breakfast or lunch, head into the town of Lenox and grab a bite at Haven Cafe & Bakery. Order an egg sandwich on challah, then take some of their signature baked goods, like a blueberry muffin or ginger cardamom scone, for the road. At the Blantyre, make a reservation at Café Boulud, Chef Daniel Boulud's inaugural Berkshire's restaurant. Dishes showcase the region's local ingredients through offerings like homemade potato gnocchi and garlic roasted chicken with kale. Dine al fresco amongst Blantyre's beautiful gardens or indulge in a gilded-age-style picnic that can be arranged for brunch or dinner.

Where to Stay

In the heart of the Midwest at Big Cedar Lodge in Ridgedale, Missouri, you can experience 4,600 acres of rolling hills and woodlands. The lodge is a fall attraction for the property's vibrant autumnal landscape, cozy log cabins, and lakeside cottage accommodations (some cabins date back to the mid-1800s). You can also check out its cool new creekside glamping experience.

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What to Do

Created as a place for travelers to enjoy nature, Big Cedar Lodge offers in-house activities for both adventure and relaxation. Head out for horseback riding at Dogwood Canyon Nature Park, book a tee time at one of the award-winning golf courses, or indulge in pampering at the 18,000-square-foot spa.

Where to Eat and Drink

Book a table at Osage Restaurant for sweeping views of the Ozark Mountains or hang out at The Buzzard Bar, which has nightly live music on the patio. To take full advantage of your surroundings, dine on Ozark-inspired food, like BBQ and slaws, at the Canyon Grill Restaurant inside the Dogwood Canyon Nature Park.