The 4 Best Places to Visit in the Fall

When you think of fall travel destinations, you may instantly picture quintessential New England towns with quaint country stores, covered bridges, and an endless supply of freshly-fallen maple leaves. But this year, we’re looking to the road less traveled to uncover four of the best places to visit in the fall for art and design enthusiasts. Where can you check into an edgy, design-oriented property and hike among ancient trees and fauna? And, is it a place the whole family will enjoy?

Thankfully, there are many small towns sprinkled across the U.S. that offer exceptional experiences for the design-minded and artfully-inclined, from California wine country and the Floridian shores to quintessential fall retreats in the Northeast. Look no further than these ideas for best fall vacations and weekend getaways, and be sure to charge up your phone or camera. Fall foliage will be going strong—and you won’t want to miss it.

1. Healdsburg, California

Soaking tub in a guest house at the Montage Healdsburg
Soaking tub in a guest house at the Montage Healdsburg. Photo courtesy Montage Healdsburg.

The first stop on our list of best places to visit in the fall brings us all the way to West Coast wine country. In a town dominated by darling bed-and-breakfasts and vineyard guest houses, Montage Healdsburg’s modern, minimalist guest pods in a milky-chocolate hue are a smart refresh for the region. But the 258-acre spread is not without Sonoma County’s famed vines. Rock-star winemaker Jesse Katz manages two nearby destinations: Aperture Cellars, a new design-minded tasting room, and Devil Proof Vineyards, boasting a 100-point Malbec featuring an image of his photographer father Andy Katz.

Designed by Delawie Architecture and EDG Design, the Montage Healdsburg opened in December of 2020. Included on site is a kids’ club called Paintbox and two pools—one for families and one just for adults (conveniently attached to the spa). Each of the guest pods feels homey with a private balcony, fire pit, and plenty of room to spread out. Complimentary rides in the resort’s Cadillac fleet into downtown Healdsburg mean you can explore the Tuesday-morning farmers’ market in the town plaza or enjoy lunch at new eateries, like the rooftop perch at The Matheson, where plating and cocktails are true works of art.

For an outdoor adventure, take a spin to Shell Beach for a hike along the coast in Sonoma Coast State Park, or Jack London State Historic Park, with a family-friendly museum honoring the late author, whose books include The Call of the Wild, The Sea Wolf and White Fang. Autumn in Northern California wine country may surprise you: yes, those leaves on the grape vines do turn!

2. Rosemary Beach, Florida

Rosemary Beach at night, one of the best places to visit in the fall
Photo courtesy Rosemary Beach.

The next stop on our list of fall destinations in the U.S. may surprise you. An alternative to the “spring break” beaches in the Sunshine State is Rosemary Beach, Florida, a New Urbanism community built from the ground up in 1995. Rosemary Beach was envisioned as a sibling to Seaside, a Floridian city just a few miles west. (If you’ve seen the Jim Carrey film “The Truman Show,” then Seaside’s colorful streetscapes will look familiar.) Most visitors book a stay in the guest houses of estates—or the estate itself—although the town’s lone hotel, The Pearl, is posh and stylish with black-and-white awnings just a block away from the Gulf of Mexico. There are just 55 rooms but with many luxuries packed in, like a spa, rooftop pool, and Havana-inspired restaurant.

Main Street’s cobblestone walkways and artful curves recall the charm of rustic Italy, and Rosemary Beach’s many restaurants, cafes, and shops mean you don’t need to pack up the car to go elsewhere for dining or fun. Nearby state parks for a day hike or stand-up paddle-boarding include Camp Helen State Park, Point Washington State Forest or Henderson Beach State Park. You’d be remiss to not rent a beach cruiser and pedal along Highway 30-A, including to Seaside’s food-truck park where retrofitted Airstreams are as much a sight as the food.

Another must is Alys Beach, located adjacent to Rosemary Beach, where the residential white-washed buildings mimic the architectural charm of Bermuda: the work of town architects Erik Vogt and Marianne Khoury-Vogt. Bonus for littles and adults alike: a beloved donut truck (Charlie’s Donuts) parks in Alys Beach every morning.

3. Catskills, New York

The Roxbury in Catskills, New York
Photo courtesy the Roxbury at Stratton Falls.

When thinking of the best places to visit in the fall, endless New England road trip ideas are bound to surface to mind. But, head just a bit further west and you’ll discover all that New York State has to offer, including Catskills.

This formerly sleepy hamlet is now where all the cool kids are opening hotels. This includes The Roxbury at Stratton Falls, a 43-room boutique-hotel experience in Roxbury owned by two former theatre-set designers. Much of the custom furniture featured on the property includes pieces sourced from Mexico City-based POLaRT—like acrylic clear plastic lamps and skull stool chairs—composed of environment-friendly polymer materials. Rooms are split between a (thankfully) refurbished 1950s motel and an historic mansion.

There’s an air of sophistication but also of whimsy, appealing to travelers of all ages. One example: Cinderella’s Gown Cottage featuring a ball gown as the bed’s canopy and a bath inside a huge molded pumpkin (oh, yes!). In addition to magical family experiences, art abounds on the property, including the Man Ray mosaic in one cottage’s shower and indoor Faerie Forest in another.

Hiking and bicycling within fall color extends in every direction once you leave the hotel, with bountiful recommendations on the Visit the Catskills website. The 26-mile Catskills Scenic Trail stretches from Bloomville to Roxbury along the former Ulster & Delaware Railroad. Even if you only do a part of it, plan on seeing farms, forests and mountains. In 2004 the National Park Service awarded Roxbury a “Preserve America Community” designation, proof of its commitment to preserving architecture and wild, open spaces.

As an alternative stroll, take a walk down Main Street and you’ll find an array of galleries, cafes and restaurants to explore.

4. Aurora, New York

View of the Rowland House at the Inns of Aurora, one of the best places to visit in the fall
View of the Rowland House at the Inns of Aurora. Photo courtesy Inns of Aurora.

Last but certainly not least on our list of best places to visit in the fall is the Finger Lakes village of Aurora, New York.

Hugging Cayuga Lake in Western New York and home to just 700 residents, Aurora boasts both Arts & Crafts and modern-art influences. For example, you can check into one of the five restored historic homes at the Inns of Aurora, stocked with works of art by blue-chip contemporary artists like David Hockney. Owner Pleasant Rowland — best known for launching the iconic American Girl brand — has even filled in the décor with her very own antiques collection, including remarkable 14th-century Chinese chests, hand-beaded chairs from South Africa, and carved English mirrors. For the artfully inclined, guests can try their hands at plein-air art with the opportunity to check out an easel stocked with paper and watercolor paints.

New this fall is the 15,000-square-foot Spa at the Inn of Aurora, designed by Hart Howerton, a firm whose other projects include The Island House in the Bahamas; and Four Seasons properties in both Santa Fe, New Mexico and Scottsdale, Arizona. Art even hangs in the spa.

Then, consider taking a trip west on the New York Thruway to the village of East Aurora, located southeast of Buffalo. There you’ll find the Roycroft campus, a living-history museum with tours and shops for skilled crafts (printing, copper and furniture). During the late 19th century, this campus spawned the Arts & Crafts movement by hosting a guild, later named a National Historic Landmark in 1986. Nine of the 14 original structures are still standing today. Rooms at the intimate 1905 Roycroft Inn include breakfast and are adorned with Arts & Crafts-style furnishings. The 633-acre Knox Farm State Park, a haven for hiking, is just two miles away — as is the former country estate for the Knoxes.

For a glimpse at fall color, you need only to peek out the window. Fall foliage in Upstate New York is full bloom beginning as early as the last week in September, and generally extends through mid-October.

For more travel inspiration, see New England vacation ideas here.