Puerto Rico
Culebra, Puerto Rico. You want to go to here, right? Right. | Cole Saladino/Thrillist
Culebra, Puerto Rico. You want to go to here, right? Right. | Cole Saladino/Thrillist
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The Best September Travel Destinations to Extend Your Summer

No one ever closes out summer feeling like you did everything you wanted, all the stuff you dreamed up back in May. And yet, you’ve probably been doing a lot. Maybe took some weekend trips. Maybe hit some music festivals. Summer, even as an adult, is still the season that feels most like it operates outside the patterns of your actual life. Once autumn hits, it’s time to enjoy all the things close to home, to find the best of what’s in your own backyard: hiking trails, food festivals, state fairs.

September, if you aren’t tied down by the dawning of a new academic calendar, is a phenomenal month to sneak in that one final trip you never got around to this summer. September ushers in that all-too-brief summer vacay sweet spot -- surge pricing has ended, but sunshine and warm nights remain. Music festival season gives way to harvest festival season. September vacations mean cheaper prices, better weather, and smaller crowds. Here are the best of ’em, for your consideration:

Acadia National Park, Maine | Romiana Lee/shutterstock

Acadia National Park, Maine

Coastal Maine is home to one of the smaller national parks, Acadia, which bills itself as the site with the least light pollution east of the Mississippi River. Accordingly, you must go there for the Acadia Night Sky Festival (September 25-29). Astronomers both amateur and professional come together with the rest of the locals to stargaze, and to partake in other sources of good clean fun like artwork contests and telescope raffles. September is already the ideal time of year to visit Acadia, since the crowds have thinned and the weather is becoming brisk, as outdoorsy people are wont to say. I don’t even really like hiking that much, but I loved hiking in Acadia.
More: Why Maine is the best state for your end-of-summer getaway

The Cyclades, Greece

Obviously the Greek islands are a very special tier of beautiful at any time of year, but they get so hot in the summer months and, depending on where you go, crowded past the point of being pleasant. As someone who grew up visiting these, I can think of no specific reason why they’d be more enjoyable in the pits of summer than the off-season. Try Santorini or Mykonos if you want something a bit more lively, but if you’d rather spend a week eating fresh octopus in a sleepy fishing village with a population of a few dozen, choose from a number of (my favorite) under-the-radar Greek islands. Also! The proper pronunciation of “gyro” is “YEE-ro,” and the proper way to serve one is with the fries on the inside, the way they’re done here.
More: Pick out a stunning Greek isle that won’t be crawling with American tourists

Glens Falls, New York

For nearly 50 years, this city on the edge of the Adirondacks has held the Adirondack Balloon Festival, a hot-air balloon extravaganza that looks straight out of a children’s book. There could be as many as 100 balloons aloft at once, and after dark you’ll still see 30 or so lift off for the “moonglow,” which everyone watches by flashlight. This year’s festival runs September 20-23, and there’s also a craft fair that funds Good Shit in the local community like scholarships and service projects. On September 29, Glen Falls City Park hosts the Taste of the North Country food festival, with participating local restaurants offering up delicious samples for just a buck or two (admission is $5 for adults; those under 18 get in for free). Good food, good vibes, balloons, and you’re in upstate New York in early autumn -- you know this is the right call.
More: Other small towns upstate New York you should totally check out

Humantay Lake, Cusco, Peru | Anna Gorin/moment/shutterstock

Machu Picchu, Peru

The Salkantay Trek is basically a less famous but more awesome alternative to the Inca Trail, and September is one of the best times to hike it. Your best option is probably the five-day trek; make sure to first give yourself a couple of days in Cusco to acclimate to the 11,000 feet of altitude, though you’ll be heartened to know that I neglected to take any medication for it (aside from coca leaf tea, which you will be offered and should drink) and threw up but twice. Salkantay Trekking will set you up with guides (if yours are Oscar and/or Willie, please pass on my regards!); meals (like, way more good food than a human could conceivably eat in one sitting); horses (to carry some of your stuff, though you can ride them if you need a break at any point); and accommodations (you can sleep in one of those glass igloos that got trendy when Iceland did) for under $500. 2019 is also the first year the Machu Picchu citadel has been wheelchair accessible.
More: How to actually make your Machu Picchu dreams come true

Colorado’s Dillon Reservoir, near Breckenridge, is spectacular in September as aspen trees begin to turn in the mountain air. | Brendan Bombaci/500Px Plus/Getty Images

Breckenridge, Colorado

Oh, did you think Breckenridge was only good for skiing in the winter? Because same, and I’m actually from Colorado so this is more embarrassing for me. If you are of legal drinking age, you should strongly consider visiting Breckenridge in September for Breckenridge Oktoberfest. What’s advertised as the largest street party in the Rocky Mountains runs from September 6-8. If you can stay for a week, you should, not only to enjoy walking around the adorable downtown but to take advantage of the Breckenridge Wine Classic from September 12-15. The brisk air, which in my very unbiased opinion is the best-smelling in the world, the shimmering golden aspen trees, the fact that you’ll be able to feel your toes -- it’s all good.
More: Nearby Frisco, Colorado, is pretty freakin’ great too

puerto rico
Flamenco Beach is considered the crown jewel of Culebra Island in Puerto Rico. | Cole Saladino/Thrillist

Puerto Rico

September will mark the two-year anniversary of Hurricane Maria’s landfall on the island of Puerto Rico, and there’s never been a better time to visit. September indeed falls during hurricane season in the Caribbean, but that spans June through November, so what September likely means for you here is that you can enjoy steeply discounted hotels and airfare, and lounge on Puerto Rico’s most beautiful beaches free of crowds. Walk through Old San Juan and eat mofongo and salsa dance in the street and look at the bioluminescent bay under a new moon (which falls on September 28 this year). Or escape the capital city and explore the rainforest, the surf towns, the roadside kiosks selling delicious deep-fried snacks. Despite recent political protests and a new head of government, tourism is undeterred -- Puerto Rico is open for business, and that business should be you.
More: The ultimate Puerto Rico travel guide

Seems like a solid place to drink some bourbon. | Kentucky Bourbon Festival


Cool neighborhoods like Butchertown and Germantown are giving reason to visit Louisville anytime, but September is when an already great Bourbon scene gets even better. A short drive from Louisville in Bardstown, the Kentucky Bourbon Festival runs from the 18th to the 22nd, and is loaded with bourbon tastings, mixology classes, art displays, car shows, and/or food vendors, which works out to like, 746 things to do in total. Some events are ticketed, but there are plenty that are free. Then, in Louisville proper, from September 20-22 you have Louisville’s Bourbon & Beyond -- a bourbon, music, and food festival headlined this year by Foo Fighters, Hall & Oates, and Zac Brown Band. And despite the theme, it’s open to all ages -- children under 5 don’t need a ticket.
More: Why Louisville is one of America’s most underappreciated cities

beluga whales
Impossible to not have your mood improved by seeing even a single beluga whale. | David Merron Photography/Moment/Getty Images

Manitoba, Canada

Manitoba is rich in the kind of seasonal local festivals you crave, but first things first. Late summer through early fall is beluga whale season in Manitoba, which sees more belugas this time of year than any other site on the planet -- some 60,000 -- and there are a number of boating and kayaking tours you can take to get right up close. If you get there for Labor Day weekend (or Labour Day weekend, since you are in Canada) you’ll find entry to the provincial parks is free. If you visit the province during, say, the weekend of September 6-8, you’ll still catch the tail end of beluga season (and the prime weather, though the leaves are also just starting to turn) while also getting to enjoy the free Manitoba Dragon Boat Festival, the Honey, Garlic & Maple Syrup Festival, and Winnipeg's largest annual street festival, ManyFest. And maybe the Northern Lights.
More: If you love Canada so much why don’t you marry it

washington state fair
Good clean family fun at the annual Washington State Fair. | Washington State Fair


September is the start of fall festival season, and Washington does it right. The Washington State Fair kicks off August 30 and runs til September 22nd. There will be dog shows. 4-H shows. Horse shows. Art shows. The world’s biggest bounce house. Concerts, rodeos, rides, food vendors, local artisans selling quilts and ceramics and pies, really just everything you could want from a state fair (tickets start around $11 for adults). From September 6-8, Port Townsend hosts North America’s largest wooden boat festival -- more than 300 vessels -- which is good family fun for anyone who loves boats or just wants to get on the water for a day. September 7th, the Skagit River Salmon Festival provides family-friendly live music, a beer and wine garden, local handicrafts, and educational booths for everyone to come out and celebrate the bounty of the Skagit River (that would be the salmon). Close out the month with Leavenworth’s Bavarian-themed Autumn Leaf Festival on September 29th.
More: Actually cool things to do in Seattle

Don't miss the Taos Fall Arts Festival -- it's one of the highlights of the season. | Michael DeYoung/Getty Images

Taos, New Mexico

There are few places more stunning than a desert when the air has cooled and the hazy grit of summer has cleared. Along with late spring, early fall is the most pleasant time of year to visit New Mexico. From September 5-7, fans of Folk and Bluegrass music can head to Kit Carson Park to two-step their way through the beloved annual Big Barn Dance. September 13-14, local artists transform the town for the Paseo Project, installing interactive light and sound exhibits and staging public performances throughout the downtown area. The crown jewel of the season in Taos, long renowned as an artists colony, comes September 20-29 -- the return of the annual Taos Fall Arts Festival. Visitors from across the country join locals in what’s become a marquee event for the visual art community, with the town’s many resident artists exhibiting their works. It’s the oldest arts festival in Taos, and your chance to catch the work of up-and-comers alongside the celebrated veterans.
More: Other fine places to get weird in the desert

Please send us postcards from the annual Running of the Weiners. | Oktoberfest Zinzinnati

Cincinnati, Ohio

Cincinnati, as you might have guessed by this point in the list, is at its most pleasant in September. On Labor Day weekend, the city puts on an annual end-of-summer celebration, Riverfest, that includes one of the largest and most impressive fireworks displays in the Midwest; also, the Rubber Duck Regatta. And as Oktoberfests the world over get a jump on things in September, Cincinnati is inarguably the top-tier destination for Oktoberfesters who don’t actually plan to cross an ocean for the festivities. From September 20-22, Cincinnati’s vibrant German roots are on display for Zinzinnati, the largest Oktoberfest celebration in America. Don’t miss the legendary chicken dance (also the world’s largest) nor the Running of the Wieners (dachsunds, dressed as hot dogs, race very short distances).
More: All the things to do in Cincinnati

Check out Yellowstone in September, once all the noisy schoolchildren have gone. | Kevin McNeal/Moment/Getty Images

Yellowstone National Park

Though its most iconic photographs come out of Summer and Winter, Yellowstone has so much to do any time of year. But seeing Yellowstone in September is, in a number of ways, the best of them all. In September, you’re catching the park immediately after the peak tourist season has thinned, but before the roads have closed for the winter. The screaming children who scare off all the good wildlife have been taken away. The hiking trails that were impassable the whole first half of the year due to snow are open. The bears are out, but not at their hungriest. If you’re the outdoorsy type, maybe the type who prefers a peaceful trip taken alone, away from civilization, maybe do some fishing, then September in Yellowstone is for you. Brown trout are spawning, elk are rutting, biking is more enjoyable now that the park is suddenly not clogged with car traffic, and you can actually take your time at the various geological wonders without getting elbowed by frenzied children on summer vacation.
More: The ultimate Yellowstone National Park travel guide

Planning a trip for a different time of year? Check out our monthly travel recommendations for the best places to travel in January, February, March, April, MayJuneJuly, August, October, November, and December

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Kastalia Medrano is Thrillist's Travel Writer. You can send her travel tips at kmedrano@thrillist.com, and Venmo tips at @kastaliamedrano.