Fall has become more 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.
If you’re planning a getaway this fall, there are plenty of sleepy towns across America that boast the right crisp temps and cozy vibes, making them ideal locales to pull on wooly socks, catch up on Zzz’s, and bask in the complete and total relaxation of fall splendor.
For destination recommendations, we checked in with travel experts Tanner Saunders, Bree Green, and Nikki Vargas for their favorite spots, along with my own, as well as a few insider tips to keep in mind once you’ve booked and begin to plan your trip.
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.
Joey Skladany: Looking for a mountain escape? Asheville is nestled among the Blue Mountains, offering unbeatable views and an even more unbeatable food scene. Book a stay at the trendy Foundry, which puts you right smack in the middle of downtown so you can experience all of the shops, bars, and eateries that the charming town has to offer. I recommend Nine Mile, a Caribbean-inspired, vegetarian-friendly restaurant with a variety of award-winning hot sauces. If you’ve got fall foliage on the brain, nothing really compares to the fiery yellows, oranges, and reds that will canopy you on every sidewalk.
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.
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.
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.
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.
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.
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.