Fall has become more of a state of mind than a season — conjuring soft sweaters, pumpkin-spiced scents, crackling fireplaces, and technicolor foliage — all best enjoyed in a scenic, sleepy town. The problem with the good ol’ U.S. of A (and it’s a good problem to have) is that there are too many adorable storybook cities to choose from, making an October or November escape quite difficult for those of us who are indecisive.
To help narrow your search, we reached out to travel experts and editors Tanner Saunders (The Points Guy), Bree Green (Travel + Leisure), Nikki Vargas (Fodor’s Travel), and yours truly for autumn-time destination recommendations, as well as a few insider tips to keep in mind once the trip has been booked and the itinerary planning begins.
These spots boast the ultimate cozy vibes that call for woolly socks, long afternoon naps, and spontaneous jumps into oversized piles of leaves. Check out our top picks below.
Round Top, TX
Tanner Saunders: With a population of less than 100, Round Top, Texas, is charming and quaint but full of little surprises like Royers Cafe and the eclectic Junk Gypsy shop where you can find plenty of treasures for your home. It’s the kind of place where people sit on the porch drinking coffee while the world slowly passes by. However, twice a year, the sleepy town wakes up, for a miles-long antique festival during which thousands of people come to shop for odds and ends.
Greenville, SC
Joey Skladany: Greenville more than lives up to its name with an abundance of outdoor spaces and trails to walk, bike, and picnic, but it swaps the green for orange, yellow, and red during fall, offering a nature-forward oasis for anyone lucky enough to pop in for a visit. After a day of exploration, head downtown, where dozens of establishments show off local talent at art galleries, restaurants and cafes, and boutique clothing stores. It resembles the quaint Southern town that’s often depicted in Hallmark Movies and is a wonderful alternative to livelier and more touristy Charleston.
Woodstock, VT
Saunders: Like a town ripped right out of a Hallmark movie, Woodstock, Vermont, is a dreamy place to see the leaves changing in the fall while learning how fresh maple syrup is made out in the woods. In town, there’s a strip of charming stores, and if you wander around enough, you’ll run into a picture-perfect covered bridge.
Mackinac Island, MI
Bree Green: As someone who was born and raised in Detroit, Mackinac Island was just a road trip away, with its beautiful foliage and delicious, classic small-town fudge. Booking your stay at one of the historic local hotels, like Grand Hotel, or bed-and-breakfast accommodations is a must.
Taos, New Mexico
Skladany: The desert may not be the first place that comes to mind as temperatures dip, but nothing beats a mild fall hike off of the region’s 84-mile Enchanted Circle Scenic Byway. But don’t just treat the Western gem as a quick road trip stop — it’s chock-full of adobe buildings and a thriving Native American community where you can purchase one-of-a-kind artwork, beaded and gemstone jewelry, handwoven garments, and an array of wellness-minded beauty products to take full advantage of the season’s more relaxing mood.
Franklin, TN
Saunders: About half an hour outside of bustling Nashville, Franklin, with its Main Street downtown area, is like a Southern version of the fictional Stars Hollow in “Gilmore Girls”. Full of beautiful homes and cute shops, the town is ideal for a fall stroll — grab a banana iced coffee at Frothy Monkey to enjoy as you take it all in. To really soak up the season, make a pitstop at Gentry’s farm for hot apple cider and a corn maze.
Poconos, PA
Green: A longtime favorite of New Yorkers seeking refuge in the winter months, the Poconos is the snowy getaway you need. It has resorts that guarantee a romantic couple’s retreat or, for families, quaint cottages you leave only to indulge in the various outdoor activities offered.
Eureka Springs, AR
Skladany: All eyes are on the Ozarks when it comes to stunning fall foliage, and the mountainside town of Eureka Springs is at its epicenter with scenic paths and overlooks that out-of-towners drive out of their way to visit and photograph. Aside from its jaw-dropping natural beauty that resembles a classic Bob Ross painting, the friendly area also brims with beloved small businesses, ranging from bookshops and bakeries to diners and breweries. In fact, all of Northwest Arkansas is having a bit of a moment, so treks to nearby Bentonville and Fayetteville are also musts if you’re dedicating a few extra days to the appropriately nicknamed Natural State.
Cannon Beach, OR
Nikki Vargas: When visiting Cannon Beach in the fall, during the offseason, the hotel prices drop, the crowds become sparse, and the town seems to epitomize autumn. You wake up with the sun and explore the tidepools dotting the base of Haystack Rock. In the afternoon, you can go hiking at one of the many nearby parks to take in that lovely, melancholy Pacific Northwest weather. In the evening, you can have wine and s’mores over a beach bonfire. If going, I highly recommend staying at the Surfsand Resort, which puts you within feet of Haystack Rock and offers a myriad of activities to enjoy, from cookie hour to bonfires.
Hobart, NY
Vargas: Arguably, it doesn’t get more sleepy or charming than Hobart, New York. Notably, this Catskills town is a book village where you’ll find more quaint bookshops than shops or restaurants. For any bookworm, Hobart is a great town to spend a day roaming the many bookshops that line its Main Street before continuing on to one of the many sleepy towns that dot New York’s Catskills and Hudson Valley.
Rapid City, SD
Skladany: Adjacent to Custer State Park where you can camp, hike, and literally roam with the buffalo, Rapid City is like a tiny Midwestern Brooklyn but with direct access to all things nature. Its coffee shops and restaurants boast eclectic, chill, hipster-esque vibes, which is a unique and welcomed backdrop to the more energizing trails and rivers you’ll likely explore during a visit. This contrast makes it the perfect spot for anyone traveling in a group or with someone who has a different set of vacation priorities — you can spend the day on the go but return to a town where life is just a little bit slower paced than the norm.
Palm Springs, CA
Green: Aside from Coachella, Palm Springs is typically the kind of city where you quite literally sit back and relax. I’ve experienced the most serene moments at dusk, when the sunny desert is a bit cooler, while watching the clear starry view from a beautiful Airbnb.
Bloomington, IN
Vargas: Having earned my undergraduate degree at Indiana University, I am admittedly biased about adding Bloomington to the mix. But Bloomington is, in fact, a stunning college town whose gothic architecture becomes hauntingly beautiful once flanked by autumnal foliage. Kirkwood Avenue is lined with stellar restaurants, cute bars, and (if memory serves me correctly) a slew of boutique shops worth checking out.
Naples, FL
Skladany: I may be biased by including my hometown on this list, but autumn is the perfect time to visit Southwest Florida before the snowbirds descend. By October, most of summer’s intense humidity has dissipated, yet the Gulf of Mexico remains warm enough for a quick dip or wade through the sandbar in search of seashells. And while coziness may not come in the form of chunky scarves and warm woolen mittens, there is no denying that a nap in a hammock or lounge by the pool can bring a necessary wave of calm and relaxation before the holiday madness.
