Fall long weekends used to mean defaulting to foliage. Book a B&B, pretend cider is exciting, maybe panic about how much fleece is too much fleece. But these days, the smartest travelers are mixing it up. Some classic destinations (hello, Berkshires and Adirondacks) are still in their prime, yes—but they’ve quietly leveled up. Think new design-forward hotels, festivals that feel more curated than quaint, and restaurants doing a lot more than serving “harvest bowls.” Meanwhile, lesser-known spots—desert towns, off-season islands, wine regions south of the usual suspects—are hitting their stride just as everyone else heads back to the office.
This is the sweet spot: after the summer stampede, before the holiday congestion, when flights and hotels are cheaper (around 20 to 40 percent less, according to Expedia), tables are available, and even the most over-it concierges start making eye contact again. Fewer families, more actual atmosphere. And thanks to the cosmic alignment of school calendars and shoulder-season pricing, you can pull off something that feels like a full reset in 72 hours or less.
We’ve rounded up 13 places that thrive in fall, whether or not they’re known for it. Some are stalwarts with new energy; others are late-blooming alternatives to the usual suspects. All have something going on, whether it’s an art festival, a reopening, or a hike that won’t be swarming with backpacked influencers. So whether you’re chasing peak foliage or just a decent Negroni away from home, here’s where to go when the forecast and your calendar finally agree.
The Best Long Weekend Trips to Make the Most of Autumn
Bayfield, WI
At the northern edge of Wisconsin, just far enough upstate to avoid sprawl and self-promotion, Bayfield is the kind of place Midwesterners only mention after you’ve passed the unspoken vibe check. With fewer than 600 residents and zero interest in reinvention, it sits on the lip of Lake Superior. Offshore, the Apostle Islands hold their stoic formation—22 pine-cloaked landforms rising from the water like they’ve been ignoring your drone long before you owned it. On land, Rittenhouse Avenue keeps things refreshingly unbothered: a bookstore with taste, a coffee roaster with opinions and art galleries that don’t feel compelled to explain themselves. In October, Apple Festival rolls in with brass bands, caramel everything and just enough Midwestern chaos to keep things charming. For those leaning into their Scandinavian era, Wild Rice Retreat delivers heated floors, cedar saunas and Nordic-style cabins that make skipping town feel like a wellness decision. Hoop’s Dockside serves perch and picnic tables without fanfare. The Copper Trout keeps it low-key excellent: fresh whitefish, housemade pasta and zero risk of a 10-minute monologue about foraging. It’s the kind of town where everything hits quietly—until you realize you’re already planning your return.
Courtesy of Bayfield Wild Rice Retreat
Charleston, SC
Fall in Charleston feels like the city letting its shoulders drop. The air clears, the humidity retreats, and suddenly the streets feel less like a film set and more like a functioning port town with layers worth peeling back. MOJA Arts Festival (Sept. 25 to Oct. 5) weaves Afro-Caribbean music, dance and visual art through backstreets and courtyards without fanfare. Come November, the Charleston Food & Wine Classic (Nov. 14 to 16) grabs headlines, but the real culinary energy hums under the radar—chefs staging intimate dinners in borrowed spaces for diners who know better than to ask for a menu.
Fall rituals here aren’t for show. Oyster roasts pop up under centuries-old live oaks, and ghost tours stretch into late November, threading folklore through alleys that predate the nation. For a nature reset, locals drift inland to Cypress Gardens, where cypress knees pierce blackwater pools under a canopy of flame-orange leaves. Others head to Shem Creek, where herons patrol the docks and locals argue over shucking technique with the enthusiasm of a contact sport. Charleston’s hotel scene, long defined by either legacy or spectacle, is seeing smarter entries. The Nickel, in Cannonborough, offers 50 apartment-style suites, a low-lit cocktail bar and a rooftop with views that trade flash for atmosphere. On a coveted waterfront plot, The Cooper opens in October with five new restaurants and an infinity pool, which may remain the talk of the town until the new Four Seasons flings open its doors in 2028.
Courtesy of The Nickel Hotel; Photo by Matthew Williams
The Adirondacks, NY
Fall in the Adirondacks is nature with an off-ramp. You’re deep in forest—millions of acres of it—but your cabin still comes with a heated towel rack and a pour-over setup. This is the season when the region sheds its summer busyness, yet keeps the polish. The Adirondack Rail Trail is slowly coming online; a crushed-stone path linking Lake Placid to Floodwood Road, with the final stretch to Tupper Lake expected by fall 2025. For now, the ride’s already worth it. Want a one-way glide without a U-turn? BikeADK, a Saranac Lake-based crew of trail whisperers, will shuttle you, your gear, and your expectations back to start. Book ahead. As the foliage hits peak saturation and the crowds thin, cyclists roll past marshes and moose-crossing signs that aren’t just props. Hikers veer toward café-lined Saranac Lake or the stillness of Connery Pond. If the forecast turns moody, duck into the revamped Lake Placid Olympic Museum for a dose of retro ambition and mid-century charm. Come evening, Bluebird Lake Placid delivers a low-lit, Japandi-leaning refuge with just enough attitude. Ask nicely and there might be an off-menu toddy that hits like a local secret.
Courtesy of Bluebird Lake Placid
Louisville, KY
Fall in Louisville hits all five senses, with brass bands, barrel-aged bourbon and just enough horse sweat to remind you where you are. From September 11 to 14, Bourbon & Beyond floods the city with high-proof spirits, big-name headliners (think Jack White and Phish) and culinary flexes from the likes of Edward Lee and Elizabeth Banks, the latter pouring her own Archer Roose wines. Come October, the mood shifts from loud to leisurely with the St. James Court Art Show, a sprawling open-air gallery set against Old Louisville’s Gothic-revival mansions and gaslit sidewalks. Over 600 artists show up, slinging everything from sculpture to Appalachian folk crafts without a trace of Etsy energy. Equestrians, or just those who enjoy the pageantry without the pressure, plan around Churchill Downs’ Fall Meet (Oct. 26 to Nov. 30). Think fewer fascinators, more trackside brunches and behind-the-scenes tours with actual grit.
Base yourself at the newly opened Hotel Bourré Bonne, where French polish meets Kentucky swagger. It’s walkable to Whiskey Row and NuLu, but also has its own rhythm—croissant loaves and caviar upstairs, bourbon-barrel installations and skyline views from the rooftop bar downstairs. Whether you’re tailgating at L&N Stadium, gallery hopping on Market Street or sipping something brown in the Back Door bar, Louisville in fall runs deep, warm and just a little bit wild.
Courtesy of Hotel Bourré Bonne
Orcas Island, WA
Getting to Orcas Island takes commitment, including the Seattle flight, a two-hour drive to Anacortes, then a ferry, but that built-in friction is exactly what keeps it from turning into just another West Coast weekender cliché. Once you land, the pace shifts. Turtleback Mountain and Mount Constitution stay quiet, save for deer and the occasional local hiker who clocks your rental plates and nods in approval. October is peak whale season and peak foliage, but (thankfully) not peak lodging prices. Rooms open up, rates come down, and long weekends suddenly feel feasible. The Village Inn offers a polished landing pad in Eastsound with EV chargers, recycled-bottle carpets and clever design choices. Even more essential? A reservation at Matia Kitchen, now permanently housed in the former Rose’s Café space. Chef Avery Adams turns hyper-seasonal Salish Sea sourcing into something far more interesting than standard farm-to-table fare, all from a chef’s counter that feels equal parts atelier and dinner party. Elsewhere, New Leaf Café handles storm-watching breakfasts with eggs Benedict and foraged chanterelles. At the Barnacle, seaweed might make its way into your martini—and somehow, you’ll be just fine with that. Ferry in early Friday, ferry out late Sunday, and let the tides (and maybe a local bartender) set the tone.
Courtesy of Satya Curcio Photography
The Berkshires, MA
Once the lawn chairs and weekenders clear out, the Berkshires settle back into their natural flow with a tad more self-possession…and that’s despite the leaf-peeping crowds. This is a region that predates the algorithm, built instead for Wharton, Melville and Rockwell—the people who knew a thing or two about needing space to think. The design set is gravitating toward Prospect, a new 30-acre retreat in Egremont from the Rivertown Lodge team, where 49 cedar-clad cabins sit lakeside with floor-to-ceiling glass, heated floors and wood-fired stoves ready to erase your last 40 tabs. The Cliff House, its more elevated cousin, throws in Taconic views and a hot sauna with no agenda but stillness. Culture doesn’t clock out here either. MASS MoCA keeps its edge with bold-scale installations in a former mill and late-night jam sessions during FreshGrass (Sept. 19 through 21). In Lenox, Doctor Sax House retools the old mansion template with moodier interiors and a basement cocktail bar that leans beatnik, not Bridgerton. Upstairs, Dulu skips tired prix-fixe formulas for Persian-accented small plates and seasonal improvisation. If you’re lucky, Tuesday night dinner might feel like the start of something. The kind of trip you don’t post about, at least not right away.
Courtesy of Cliff House; Photo by Cole Wilson
Bermuda
In the fall, hurricane season scares off the crowds, which is exactly when Bermuda gets good. From mid-October through mid-November, this Atlantic outpost hits its stride: temperatures settle in the 70s, the ocean still holds summer’s warmth and iconic beaches like Warwick Long Bay feel practically private. Smart travelers claim the 18-mile Bermuda Railway Trail, biking the old “Rattle and Shake” line through dramatic coastlines and cedar groves past the timeworn Somerset Drawbridge. With fewer tourists around, you’ll trade real good mornings with locals who’ve synced up with the beat of island life. Skip the cruise scene in Hamilton and head for St. George’s, a 400-year-old UNESCO town where mornings stretch long and Dark ‘n’ Stormy drinks land with proper bite, made with Gosling’s Black Seal rum and Barritt’s ginger beer, the way they’ve been mixed here since 1806. The Taste of Bermuda festival (Oct. 9 to 12) spotlights homegrown chefs and distillers in street-level celebrations that feel refreshingly unbranded. Clifftop Azura on Warwick’s South Shore makes the ideal base, with apartment-style suites, floor-to-ceiling Atlantic views and multiple saltwater pools that mimic the ocean’s polychromatic tones.
Courtesy of Azura
Hudson Valley, NY
For tri-state dwellers, Hudson Valley is the default day trip, predictable unless you know when to go. Skip the weekend wine trains and bachelorette chaos for midweek, when the region’s more sophisticated self shows up. The wine scene just leveled up with Klocke Estate, a $21 million Claverack property where the minimalist tasting room doubles as a contemporary art space, pouring riesling and cabernet franc from vines that catch Hudson River light. A One&Only resort is also breaking ground near the Culinary Institute, hinting at upstate luxury’s next era. Book Wildflower Farms for proper leaf-crunching walks, an actual working farm and the best hotel spa north of Manhattan.
October peaks with the Hudson Jazz Festival (Oct. 3 through 5) at Basilica Hudson, where Julius Rodriguez and Joel Ross bring heat to the warehouse scene before it turns twee. Over in Chatham, FilmColumbia screens future Oscar nominees while maples burn bright outside. For dinner, grab a table at the Culinary Institute’s student-run spots, where tomorrow’s James Beard winners practice on duck confit with local apples. Save a day to loop Cold Spring to Beacon, collecting bruised apples bound for cider, candlelit barn concerts, antique scores and private estates that only open when leaves turn gold.
The Henson
Savannah, GA
Summer’s heat finally lifts, Spanish moss goes from sticky to cinematic, and Savannah slides into its most irresistible season. The city’s famed oak canopy becomes a frame, not just shade and the historic grid reads less like a movie set, more like a functioning neighborhood. The 2025 debut of Municipal Grand raises the bar, set in a restored midcentury bank with Death & Co. at the helm, velvet-drenched sunken lounges and a rooftop pool reserved for guests only, bathed in late-afternoon gold. Outside, Forsyth Park’s farmers market piles high with satsumas and still-warm pecans while vendors hawk Savannah red rice from Carolina Gold varieties.
Skip the carriage tour and wander Bonaventure Cemetery at dawn, when mist threads the live oaks and the quiet does all the heavy lifting. SCAD’s fall art walks animate forgotten corners, a reminder that Savannah’s creative pulse never dulled. At The Grey, chef Mashama Bailey’s guinea fowl arrives with field peas that taste like October—earthy, just harvested. Book a table at Cotton & Rye for cocktails made with local honey and Georgia muscadine. The shrimp boats still work the Wilmington River, bringing in white shrimp for Low Country boils that stretch past midnight.
Courtesy of Municipal Grand; Photo by Kelly Calvillo
Sedona, AZ
Sedona won’t stop talking about vortexes, but come fall, the town finally earns the mystique. The air turns crisp, the canyons blaze in high-saturation reds and oranges, and the volume of SUV yoga decals drops to tolerable levels. The adults-only Ambiente is upping the stay game with 40 atrium-style suites suspended over the landscape, wrapped in floor-to-ceiling glass and crowned with rooftop decks that do most of the meditating for you. West Fork, Bear Sign and Boynton Canyon hit peak foliage by mid-October, while Secret Canyon rewards early risers; park at Dry Creek Road before 8 a.m. to avoid the Instagram hordes. Stargazing hits its stride in fall; Fay Canyon and Baldwin Trailhead offer wide-open skies where the Milky Way actually shows up. Meanwhile, the Verde Valley Wine Trail is mid-harvest, so opt for guided tastings at Page Springs, DA Ranch or Javelina Leap, where malvasia bianca thrives in the high desert heat. For art and local flavor, Sedona Arts Festival (Oct. 11 through 12) keeps things rooted. Wellness seekers go full retreat mode; think horseback rides, hot-air balloons, outdoor tubs with red rock views. And at Slide Rock State Park, Fall Fest (Oct. 19) swaps out kitschy hayrides for cold creek plunges and heirloom apples that actually taste like something.
Courtesy of Ambiente; Photo by Jeff Zaruba
Palm Springs, CA
Fall in Palm Springs reads like a well-timed secret. The heat finally taps out, the snowbirds haven’t descended yet, and the desert exhales. Think crisp mornings, honey-lit afternoons, and skies so clear you feel obligated to look up. Downtown, the newly opened Thompson brings polished energy, but the insider move is Hotel Wren in Twentynine Palms, a 12-room former motor lodge turned minimalist retreat with Santa Barbara plaster, cherrywood interiors and a saltwater pool practically pointing you toward Joshua Tree’s north gate, 10 minutes away. Looking to properly recalibrate? Book into Terra, where Ayurvedic rituals, desert botanicals and stargazing soaks make even your phone want a break. Back on the cultural front, Desert X returns with site-specific installations valley-wide, and the Agua Caliente Cultural Plaza opens its sacred hot springs to the public for the first time. Indian Canyons trails reopen for hiking, vintage shops on Palm Canyon Drive wake from their summer slumber, and if you time the Aerial Tramway right—Wednesday at 4 p.m.—you’ll get golden hour without the crowd.
Courtesy of Korakia
Valle de Guadalupe, Mexico
Two hours south of San Diego, Valle de Guadalupe feels like Napa before the IPOs, complete with unpaved roads, dry-farmed vineyards and winemakers who pour what they’ve crushed that morning. This pocket of Baja California produces 70 percent of Mexico’s wine, yet sidesteps pretense with a shrug. The new Banyan Tree Veya threads in without disrupting the mood: 30 glass-and-concrete villas with private plunge pools, a grenache-only winery on-site and the valley’s first temazcal, now a full-moon ritual. Book The Winemaker’s Villa, blend your bottle before dusk, then let a private chef build dinner around it. October marks harvest season, so winemakers will hand you a glass in vineyard-crusted boots while explaining why nebbiolo thrives in these granite soils. Rent a 4WD in Ensenada (trust us on the roads there). The annual food fest lures Mexico City’s culinary elite, but roadside taco trucks still serve lengua to locals who’ve been coming for generations. At dawn, the valley smells like wild sage and fermenting grapes, a combination that somehow makes perfect sense.
Courtesy of Banyan Tree Veya
Ojai, CA
Just far enough from L.A. to shed the noise but close enough to dodge the logistical drama, Ojai trades coastline for citrus groves and hype for something resembling peace. Tucked into the Topatopa Mountains, 30 miles east of Santa Barbara, this one-road valley town operates on its own mystical frequency—part artists’ retreat, part spiritual vortex, part functioning small town. The Hotel El Roblar reboot (summer 2025) channels the kind of low-glow glamour Ojai does best: 50 clean-lined rooms, a Mexican-Californian restaurant called Condor, and Snug Bar, where the mezcal flows just as the valley starts glowing gold. In October, Ojai Day fills the downtown plaza with tamales, handmade crafts, and locals who don’t need name tags. Roadside stands are stocked with pixie tangerines and heirloom squash, while Spa Ojai’s hilltop casitas offer a version of stillness that doesn’t require a sound bath. Yes, there’s the famous “pink moment,” when the mountains light up at sunset and everyone, from the barefoot healer to the out-of-office founder, is momentarily stunned into silence. But the real magic happens on weekdays: Rory’s Place has a table, Bart’s Books (the world’s largest outdoor bookstore) stays open late, and Meditation Mount becomes your unofficial therapist.
Courtesy of The Hotel El Roblar
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