9 Gorgeous Fall Getaways Worth Visiting Every Year

Determined leaf peepers have made New England the foliage capital of the world, but the Berkshire mountains manage to retain their laidback charms despite the seasonal influx. For a visit that’s as radiant as the trees that serve as your backdrop, stay in North Adams, a Rockwellian town near the Massachusetts-Vermont border that’s dotted with churches and Victorian row houses. After a drive along auburn-fringed roads, drop your bags at the Porches Inn, then head to Public Eat + Drink for a dinner of farro risotto and pan-seared duck breast. In the morning, take in the colorful canvases at the Massachusetts Museum of Contemporary Art right next door.

Equally stunning as their New England counterparts, the roadways that wind through the Great Smoky Mountains offer their own autumnal beauty, especially in mid-October, when the treetops blaze crimson and copper. For a peaceful respite away from the crowds, hole up at Blackberry Farm, an award-winning luxury resort with one of the south’s best food programs. (The Lodge at Buckberry Creek is a more affordable alternative in nearby Gatlinburg, known as the gateway to the 520-acre national park’s waterfalls and hiking trails). To see the Smokies on a larger scale, hop aboard a historic steam engine on the Nantahala Gorge Excursion.

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This mining town is typically hailed as a winter wonderland, but the fall presents plenty of opportunities for outdoor highs. In October, ski runs transform into hiking and biking trails lined with golden foliage and a fly-fishing expedition looks like a scene straight out of A River Runs Through It. A room at boutique hotel Dunton Town House puts you in the heart of town, where you can break from rugged pursuits with a bit of upscale retail therapy—from home décor and jewelry at Picaya to designer fashion labels at Scarpe—before taking to the restorative waters at sister property Dunton Hot Springs.

Jackson Hole is a nature-lover’s paradise during the summer months thanks to its proximity to Yellowstone and Grand Teton national parks, but few realize that the autumn holds even more promise for outdoor adventure with thinner crowds and temperate weather that extends the season's best activities like hiking, biking, fishing, and more. Early September sees the arrival of the Fall Arts Festival, which hosts open-air art walks, exhibitions by local artists, and historic ranch tours. You can see it all from the gondola ride up Rendezvous Peak, then retreat to the rustic-chic rooms at Hotel Jackson.

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If autumn in New York feels a little too expected, consider its neighbor to the north. The Canadian cultural capital glows fiery red, yellow, and orange in late September and early October in places like Mount Royal Park, the Botanical Gardens, and Morgan Arboretum. Stroll the public markets at Atwater and Jean-Talon to sample the best of the season’s harvest, wander over to the historic Old Port to browse its shops before the region’s frigid winter temperatures freeze you out, then head to Mile End to indulge in one of the continent’s best restaurant scenes. Fair warning: don’t even think about trying the tasting menu at Île Flottante without securing a reservation in advance.

It’s worth braving the crowds to experience the Napa Valley’s annual grape harvest, which begins in early August and can last as late as December depending on the year. Most of the region’s vineyards and wine makers host crush parties with live music, local chefs, and tastings throughout the season; some, like Grgich Hills Estate, even let you stomp on your own grapes and blend personal bottles for a small fee. Just don’t expect to find a bargain at any of the area’s hotels. A worthy splurge: a cedar-and-glass villa at Calistoga Ranch, which sits on 157 pristine acres and offers mineral baths in its on-site spa.

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Foreigners flock to Florence during the summer months, but autumn is an even better time to visit: changing foliage gives the medieval city a painterly glow, hotel rates drop, and museums and restaurants once clogged with tourists become surprisingly accessible. Add the Tuscan wine and olive harvests—plus the food festivals that come with them—and the start of white truffle season in October, and you have all the makings of an ideal holiday. Make sophisticated Hotel Lungarno your base, then set off on culinary explorations to the city’s best new restaurants including Osteria dell’Enoteca and Gucci Osteria da Massimo Bottura, the star chef’s boîte inside the Gucci Museum.

There are few more atmospheric places to watch the foliage change than the Scottish capital, where leaf peepers have their pick of views from the tree-filled sights of the Royal Botanic Gardens to the jewel-toned panoramas of Arthur’s Seat and Calton Hill. Fall also means sweater weather, and tartans, plaids, and cashmeres are always in season here—hit Walker Slater for clothing and Anta for home furnishings. If those don’t do the trick on cool nights, there’s always a dram of scotch to warm your lungs. Do your imbibing at the Black Cat or Bow Bar, then retire in front of the fire at the Scotsman.

It’s little wonder why Cézanne and Van Gogh found so much inspiration in Provence—a fact that’s even more apparent in the autumn, when the wine harvest is in full swing, the open-air markets are packed with dried lavender and produce so lush you’ll be ruined for supermarkets, and the tourists are back home. The stone and wood guest rooms at Hôtel de Tourrel are a perfect landing spot for exploring the region’s oenophilic delights. Slip in some culture between sips: the agricultural relics at Musée des Apilles are just next door, and Cézanne’s atelier in Aix is just an hour away.