Top 21 U.S. Cities to Experience Fall Festivals and Oktoberfest

Fact checked by Elizabeth MacLennan

While the end of summer can often seem bittersweet, the fun doesn’t need to stop when you’re in a big city. As the temperatures drop and the trees turn shades of bright yellow, burnt orange, and brilliant red, you’ll want to spend as much time as you can outside before hunkering down for winter. Of course, there’s nothing like a country drive to admire the gorgeous fall foliage, but urban areas have their own autumnal charm. Imagine leaf-crunching your way through New York’s Central Park, or sipping bourbon with a chill in the air on Louisville’s Urban Bourbon Trail.

So pack up your fall travel essentials. From Savannah with its Halloween ghost tours to Santa Fe with its chili harvest, here are the best American cities to visit in the fall.

01. Denver, Colorado

The leaves start turning early in the resort towns outside of Denver, but the city’s foliage takes center stage during October. You can see it nicely from the Cherry Creek Regional Trail or along the High Line Canal, lined with brilliant yellow cottonwoods. Beer aficionados, however, might be forgiven for never noticing any trees. Fall here brings a series of beer festivals, including the Denver Oktoberfest and the Great American Beer Festival.

02. Nashville, Tennessee

The biggest parties in Nashville reflect the city’s love affair with great songs and the great outdoors. In the fall, Music City lives up to its nickname when it hosts gatherings like Americanafest, a multi-venue celebration of the country’s sonic melting pot, and September Sundown, a series of free concerts given every Friday and Saturday at Centennial Park. And as a reminder that not every lyrical turn of phrase in this town is belted out, the Southern Festival of Books takes place in October.

03. Portland, Maine

To see the best foliage in and around Portland, Maine, pedal your way around town or hike up Bradbury Mountain in nearby Pownal. After all, exercising amid the changing leaves is a convenient way to rationalize all of the good eating to be done in this seafood-loving city. Dig in at Portland’s acclaimed foodie-palooza Harvest on the Harbor. Highlights include a cocktail party, an oyster tasting, and the Maine Lobster Chef of the Year competition — where hungry audience members get to taste and vote alongside professional judges.

04. New York, New York

Autumn in New York. “Why does it seem so inviting?” asks the song. One reason may be the pastoral bliss one can find in Central Park. Check into a park-facing room at the Mandarin Oriental New York, then head to the Ramble, just south of Belvedere Castle, and wander the meadow that gets covered with red leaves from the black tupelo trees. Or head downtown to explore a stretch of the High Line — the park created out of an old elevated rail bed — between 23rd and Gansevort Streets. Well into October, you can enjoy a glass of wine from the open-air Hearth on the High Line or stop for a bite-sized treat at Doughnutterry.

05. Santa Barbara, California

It’s long called itself the American Riviera, and, like its French counterpart, this beach town enjoys a vibrant summer season. But come fall, hotel prices plummet, with the cheapest rates typically found during September. And you often get better weather in fall than summer, which can be prey to foggy June Gloom. Close to Santa Ynez Valley wine country, Santa Barbara has many tasting rooms where you can sample the local varieties. Check out Conway Family Wines, which sits on Stearns Wharf, right over the ocean.

06. Louisville, Kentucky

An estimated one third of the world’s bourbon whiskey comes from this Kentucky city, and locals toast that output during National Bourbon Heritage Month in September. You can celebrate all fall, however, along Louisville’s Urban Bourbon Trail. One stop is the Down One Bourbon Bar & Restaurant, which serves more than 160 varieties of the Bluegrass State’s trademark spirit. For a non-alcoholic stroll, check out the foliage in Iroquois Park (designed by Frederick Law Olmsted). In October, the annual Jack-O’-Lantern Spectacular displays 5,000 carved and glowing pumpkins worth staying until dark to see.

07. Salt Lake City, Utah

Autumn in Salt Lake City generally means lower prices, smaller crowds, and the chance to see bright foliage while hiking or driving along Big or Little Cottonwood canyons. This time of year also brings the Utah State Fair, held just northwest of downtown every September and featuring its own rodeo. And be sure to get your ticket for Oktoberfest, an annual celebration of beer, German food, and live music held at the Snowbird ski resort between August and mid-October.

08. New Orleans, Louisiana

New Orleans has fewer crowds and less humidity during fall, when the city’s ever-festive vibe is channeled into parties like the New Orleans Burlesque Festival, the Krewe of Boo Halloween parade, and the Oak Street Po-Boy Festival. Fall also means the return of the near-religious fervor for Saints football: before home games, you can join black-and-gold-clad locals at Champions Square, a public space right next to the Superdome, for live music, tailgating cuisine, and friendly Who Dat revelry.

09. Minneapolis/St. Paul, Minnesota

While plenty of people happily pedal around town during the depths of winter, for most locals, autumn is the last hurrah for bicycling and jogging around the lakes. Make plans to attend one of the Twin Cities’ various autumn galas, like the Minneapolis Monarch Festival, the Twin Cities Book Festival, and the Twin Cities Film Fest. To prove that you’re as hardy as the locals, go watch the Minnesota Vikings play at U.S. Bank Stadium.

10. Boston, Massachusetts

A certain back-to-school excitement fills the air in Boston, even if you’re not signed up for American Lit this fall. You can peruse the latest titles at beloved bookstores like the outdoor Brattle Book Shop or the Trident Booksellers & Cafe. This is also the best time of year to grab some apple cider doughnuts from Red Apple Farm at the Boston Public Market. Here you could also attend the Harvest Party in October, which includes a buffet dinner and live music. And to catch the best of the local foliage in the early fall, walk through the Arnold Arboretum in Jamaica Plain, part of the chain of green spaces that make up Boston’s Emerald Necklace.

11. Orlando, Florida

If you want to bring your preschoolers to the theme parks — or just ride Space Mountain over and over, without any kids in tow — the beginning of the school year is a good time to come to Orlando because theme parks tend to be lighter on the crowds. The city is more than just Disney and Universal, however. Check out the dynamic dining scene downtown and you’ll find chic options like Domu for Japanese cuisine or Enzo’s on the Lake for Italian with a view.

12. Chicago, Illinois

In the Windy City, the sweet spot for weather is during the early autumn months, when the cool air makes people feel like dancing. The punk-powered Riot Fest kicks things off September 15 in Douglass Park, followed by the Hyde Park Jazz Festival and the citywide World Music Festival. For an eclectic experience, try the North Coast Music Festival to see a variety of electronic, rock, and hip-hop artists – past headliners have included The Chemical Brothers, Kid Cudi, and Fatboy Slim.

13. San Francisco, California

This is the time of year to take a “summer vacation” to the Bay Area. While the actual summer months here are chilly and foggy, fall tends to be warm and sunny. That makes it all the better for enjoying the array of events, from the irresistible Ghiradelli Chocolate Festival to the Autumn Moon Festival in Chinatown. The only possible drawback during autumn? Rates (especially at business hotels) can be higher, since it’s peak season for conferences.

14. San Antonio, Texas

By fall, temperatures in this Texas metropolis drift out of the triple-digit range, and the locals are ready to whoop it up outside. The party lineup includes Oktoberfest at Biergarten River Walk, the post-Halloween Day of the Dead, and the Tasting Texas Wine and Food Festival. You can also either kayak along the San Antonio River or hike or bike along the River Walk’s Mission Reach portion. They’re all convenient ways to burn calories if you come for November’s Wurstfest, a 10-day celebration of all things sausage in nearby New Braunfels.

15. Anchorage, Alaska

Sure, the midnight sun is gone — but so are the highest prices and most of the cruise-ship passengers. Unlike many other Alaska towns, Anchorage doesn’t close up shop just because summer is over. There are still berries to be picked on the city’s Flattop Mountain, and you can take the Alaska Railroad up to Talkeetna to see the foliage. As leaves fall, it’s also easier to spot moose and Dall sheep that may have been playing coy behind the branches. And by night, you can start seeing the northern lights.

16. Virginia Beach, Virginia

After the boisterous Neptune Festival ends in late September, this resort city quiets down – that is unless you’re a bird or a striped bass. The big fish gather in droves in the Chesapeake Bay, and the Back Bay National Wildlife Refuge offers a perch for watching migrating ducks and snow geese — thousands of them. Another perk of the off-season: you can saddle up with Virginia Beach Horseback for rides on the sand.

17. Providence, Rhode Island

Come fall, the Rhode Island capital turns on the perfect mix of pastoral and urbane charms. While blazing foliage lights up the daytime, WaterFire — the installation of bonfires that line the city’s rivers — illuminates the evenings throughout the year during special events like PVDFest in September. Autumn also brings some quirky entertainment: Providence hosts the Vortex Sci-Fi, Fantasy, and Horror Film Festival, and The Steel Yard hosts an “Iron Pour” around Halloween, when workers turn steelwork into performance art by creating fiery sculptures from molten metal.

18. Savannah, Georgia

Against a pretty backdrop of autumn canopies, this famously haunted city swings into high gear during fall. Take your pick from Blue Orb’s City of the Dead Tour, Moon River Brewing Company, known as the most haunted place in town, and the mysterious knocks and thumps inside haunted hotels like 17Hundred90 Inn, supposedly inhabited by the spirit of a jilted servant. Nervous Nellies might prefer to focus on Savannah’s mix of culinary festivals, like the Blues, Brews, BBQ, and Bourbon Festival in October.

19. Portland, Oregon

Fall brings delicious ingredients to Portland’s locally-inspired menus: Plenty of salmon swim in the Columbia River, and butternut squash and heirloom tomatoes fall off the vines. It’s also the season for fresh hops, which have a flavor distinct from the dried hops employed by brewers the rest of the year. You can sample some excellent results at Hopworks. This time of year is also a great way to experience the culinary diversity and inventiveness of the city with unusual festivals like the Portland Fermentation Festival, where you can do some kombucha-tasting and try fermented specialties from around the globe.

20. San Diego, California

Plenty of surfers insist that autumn, the time of year when south swells mix with the season’s warm Santa Ana winds, is the best season to catch a wave in San Diego. And the Del Mar Racetrack — where the turf meets the surf, as Bing Crosby used to sing — opens its fall horse-racing season in November. That same month, you can sample acclaimed local craft brews at San Diego Beer Week.

21. Santa Fe, New Mexico

You can tell it’s chili-harvest season in Santa Fe by the smell of roasted peppers emanating from roadside stands. One great place to try them is the gastropub Fire & Hops, which tops its poutine with bacon, green chili, and white gravy. In early October, hike the foliage-lined Aspen Vista trail, about 14 miles from downtown, or drive an hour southwest to take in the “hot air” at the Albuquerque International Balloon Fiesta.