Float Into Fall with These September Travel Ideas

It seems that summer is already coming to a close (really, where does the time go?). But never fear, there’s still a few weeks of fun in the sun left. Though if you’re ready to bundle up in sweaters and order all manner of PSL, that’s (literally) cool, too. Anything goes in September, we say, even getting a jump on Halloween. Go ahead: Put out that gigantic skeleton head and start preparing your charbooterie.

This is the shoulder season for hot air balloon festivals, uncrowded beaches, and mysterious lights on the horizon in Texas (okay, that one’s all year round). There’s wacky festivals to attend—including one all about chickens inspired by the Colonel himself—plus a massive rodeo, music history immersions, art heists, and buffalo. So. Many. Buffalo.

Strap in, saddle up, and don’t forget to wear layers—it may get chilly come nightfall.

With more manageable temperatures and a few days off work, Labor Day weekend (September 1–4) has always been a go-to time for a breezy music fest. And they come in all genres. EDM in your blood? Try Electric Zoo in New York or the ARC Music Festival in Chicago. For something in a totally different direction, the 51-year-old Delaware Valley Bluegrass Festival in Pilesgrove, New Jersey bears the distinction of being the first-ever bluegrass festival to grace the Northeast, with lineups dubbed “all killer, no filler” by the Philadelphia Inquirer.

Visiting Oklahoma? Pack your earplugs for Rocklahoma in Pryor, with Rob Zombie, Pantera, Gwar, Godsmack, and Limp Bizkit. Head to Michigan for the historic Detroit Jazz Festival, or down to Colorado for Jazz Aspen Snowmass, a small fest with a big footprint featuring acts like Foo Fighters, the Lumineers, Billy Idol, and Grace Potter. There’s more than one way to send off summer in style.

Speaking of tunes, it’d be tough to beat a famed music festival’s 50th anniversary bash—especially when it’s going down under the shadow of Seattle’s iconic Space Needle. September 2–3 marks the return of the Bumbershoot Festival, with acts including Sleater-Kinney, Band of Horses, Brittany Howard, and Fatboy Slim alongside other delights like roller skating, wrestling, drag performances, and a witchy temple complete with astrology and past-life readings.

Why not make it a music-themed itinerary? Check out the Museum of Pop Culture—formerly the Experience Music Project—for the requisite Nirvana paraphernalia plus an exhibit celebrating hip-hop’s own 50th anniversary. Catch a show at the legendary Moore Theater, which grunge fans will recognize as the setting for Pearl Jam’s Even Flow music video. Go the extra mile and stay in a suite overlooking the theater, paying homage to legendary Sub Pop Records at the Kimpton Palladian Hotel. Fill out the day by hitting up the Singles house, the Paramount Theater, and the Kurt Cobain Memorial Bench. Then kick back with a cocktail at Central Saloon, the bar where Nirvana played their first show to an admittedly lackluster crowd. Hey, you gotta start somewhere.

September 23 is National Public Lands Day, which, according to the National Park Service and Bureau Land Management, stands as the nation’s largest single-day volunteer effort. It’s also a day when you can enter all of America’s National Parks for free—the perfect starting place for getting out and exploring public lands that may not have already been on your radar.

Hit Wyoming’s Killpecker Sand Dunes (where you can go sand sledding!), or the gorgeous and very under-the-radar Bob Marshall Wilderness, which spans 1.5 million acres of Montana waterfalls, lakes, and peaks—not to mention the densest population of grizzly bears in North America, so maybe brush up on your bear knowledge before setting out. Look to Mills Wilderness Adventures for a guide, or go it alone (either way, we highly recommend booking a couple nights at Blacktail Ranch). And if you have time, note that the Bob Marshall Wilderness Foundation is also looking for volunteers to help with maintenance in early September.

In September, skies are clear, evenings are crisp, and the leaves are just starting to turn colors—making them all the better to spot from above, at one of the month’s many hot air balloon festivals. Did you know that if you’re really good at piloting a hot air balloon, they let you play games in them? That’s the premise of the Great Forest Park Balloon Race, anyway, happening in St. Louis (September 15–16). Pilots try to hit a target on the ground with bean bags while spectators watch (presumably trying not to get hit themselves).

Or choose between the free Great Reno Balloon Race in Nevada (September 8–10), the Stratobowl Historic Hot Air Balloon Launch in Rapid City, South Dakota (September 8–10), the Paris Balloon & Music Festival in Texas (September 8–9), or the Lancaster Hot Air Balloon Festival in Pennsylvania (September 14–17). Hop on a ride, or just post up with a blanket and turn your gaze upward.

Perhaps it's an attempt to lessen the blow of saying goodbye to summer, but come September, we get wacky with our social endeavors. The myriad garlic festivals taking over Long Island, New York, Bennington, Vermont, Ocean Park, Washington, and other ripe destinations are tame enough, we guess. But some autumnal festivities can get a little… extreme. Like the Wisconsin State Cow Chip Throw & Festival (September 1–2), where visitors chuck cow chips—a.k.a. dried poop—for sport. It hearkens back to a time when pioneers used them as fuel to warm their houses. Now they just amuse us.

The Arcola Broomcorn Festival in Illinois (September 8–10) celebrates the prized vegetable with a sweeping contest and parade, while in London, Kentucky, you’ll find the World Chicken Festival (September 21–24). The region is the birthplace of Kentucky Fried Chicken—Colonel Sanders’ very first restaurant is now a historic site you can tour—and thus the lively chicken fest celebrates all things finger lickin’ good (BYO napkins).

Not ready to say goodbye to summertime roaming? Make the journey the destination by setting your sights on America’s top roadside attractions. Maybe you’ll find a tiny art museum, or embark on an aviation pilgrimage to Atchison, Kansas, the one-time home of Amelia Earhart and the current home of a very cool earthwork of her likeness. In Connecticut, spin around a carousel museum in Bristol, or be inspired by Mark Twain’s house in Hartford, where he penned many of his famous works.

In Salem, New York, swing by a weathered barn-turned-bookstore, or page through some tomes in the wilds of Big Sur by stopping into a house-turned-bookshop once owned by author Henry Miller. (If you’re exploring out West, make sure to graba burrito at a Maverik gas station. Trust us.) Drive alongside metal sculptures on the Enchanted Highway in North Dakota, or schedule a detour to the Klown Doll Museum in Plainview, Nebraska. Some of you might opt to keep on driving.

Summer may be drawing to a close, but that doesn’t mean you have to go all in on the back to school vibe just yet. Take a moment to reset, perhaps surrounded by pines at an all-inclusive resort set on a picturesque Maine lake, or go further—way further—by securing your own slice of wilderness in Alaska.

Visit one of quietest places in the country (hint: it’s a town in West Virginia), find peace in Denver and Austin, go off the grid in Canada’s eastern shore, or, if you’re feeling extra adventurous, scuba dive with sharks in the Galapagos. Our writer says it’s the most relaxing vacation she’s ever had. If you try it, please do tell us how it goes.

Sometimes it’s not enough to read about history—it’s way more fun to reenact it. Into art heists? Then make your way to the Isabella Stewart Gardner Museum in Boston, the site of one of the biggest still-unsolved heists involving $500 million worth of works by Rembrandt, Vermeer, Manet, and more. If you have evidence leading to the recovery of the pieces, you could take home $10 million. But first you have to know the details, and that’s where an immersive tour following in the footsteps of the robbers comes in. (If you happen to solve the crime, just remember who sent you.)

While you’re in Boston, explore it from a different angle with a stargazing adventure in and around the city. Down a pint at a family-friendly brewery, taste your way through the city’s new restaurants, or live it up like a local in a friendly neighborhood. We hear Somerville is all the rage these days.

Despite its name, Oktoberfest is actually a mostly September affair (a plot to mess with foreigners? maybe), tracing its beginnings to a rather dry celebration of the Bavarian King’s wedding in 1810. Now it’s decidedly wet, and taking place in Munich from September 16 to October 3, with the price of a hefty beer ranging from €12.60 to €14.90 (a fact they disclose on their official website, which is a nice gesture).

If you’re planning to make the trip to Germany, we’ve got some Airbnbs for consideration. And if you’re planning to hop around the country, here are some quality stop-off ideas, including Ruhrgebiet, a former industrial town turned art hub, and Rothenburg, one of the best-preserved medieval towns in Europe.

Rodeo season may be inching toward its seasonal sunset, but Oregon’s Pendleton Round-Up (September 9–16) is still rearing to go. And if there’s one to hit, this is it, a massive event imbued with a surprisingly low-key vibe and even their very own whisky. Visiting is also an immersive experience—the small town it’s named after is a frozen in time slice of Old West culture.

Originally proposed to celebrate the harvest, the Pendleton Round-Up now draws 50,000 people annually with its slogan, “Let'er Buck.” The week of events include a star-studded kickoff concert, an evening show exploring Native and Western history, a 300-strong teepee village representing tribes from all over the Northwest, and a parade.

And as long as we’re playing cowboy, let’s lean into Western Month. Every September, some 1,300 buffalo rumble through the Black Hills of South Dakota for the Buffalo Roundup and Arts Festival (September 28–30), herded by cowboys and girls in an effort to eventually test, brand, and sort the beasts as a means of population regulation. Spectators just need to show up with chairs, binoculars, and whatever else they need to keep warm and satiated in the viewing area. Just watch out for the cow–er—buffalo pies.

Want more Thrillist? Follow us on Instagram, Twitter, Pinterest, YouTube, TikTok, and Snapchat.