September is a phenomenally underrated month for travel. People seem to disqualify it because they associate it with childhood anxiety about summer ending and going back to school. Sure, summer is over on paper, but September ushers in that all-too-brief summer vacay sweet spot where surge pricing has ended while sunshine, festival season, and warm nights remain. In places all over the country and the world, September vacations mean cheaper prices, better weather, and smaller crowds. Here are the best of ‘em, for your consideration:
You Could Stay in a Giant Seashell in Mexico
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 5-9). 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 (and October, fine) is already the best time of year to visit Acadia, since the crowds have thinned and the weather is becoming brisk, as people who hike are wont to say. I don’t even really like hiking that much, but I liked hiking in Acadia.
The Cyclades, Greece
Obviously the Greek Islands are ridiculous levels of beautiful any time of year, but they get so hot in the summer months and, depending on where you go, unnatural levels of crowded. 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. By the by, 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.
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. You’ve also got the Saratoga Wine & Food Festival (September 7-9) and the World’s Largest Garage Sale (September 29-30) which is expected to draw more than 500 vendors. And look, regardless of your feelings for bric-a-brac or balloons, you’re in upstate New York in early autumn -- you know this is the right call.
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 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, ever); 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 comfortably under $500, total.
Oh, did you think Breckenridge was only good for skiing in the winter? Because same, and I’m actually from Colorado so this is likely much more embarrassing for me than it is for you. 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 will run from September 7-9. 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 13-16.
September will mark the one-year anniversary of Hurricane Maria’s landfall on the island of Puerto Rico. It will be a historic and deeply moving time to be there, when you can enjoy steeply discounted hotels and airfare, and lounge on Puerto Rico’s most beautiful beaches free of crowds. September indeed falls during hurricane season in the Caribbean, but it spans June through November, so barring any actual Maria-sized event you can expect a safe trip. Walk through Old San Juan and eat mofongo and salsa dance in the street and look at the bioluminescent bay under a new moon. The overwhelming majority of Puerto Rico is open for business, and that business should be you.
For starters, September means the return of the annual Kentucky Bourbon Festival to Bardstown from the 12th to the 16th. Each of those six days 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. The events are a mix of ticketed and free, and there is a designated Family Fun Area with train rides to distract the children while you enjoy your jazz and cigars. Then, less than an hour away, from September 22-23 you have Louisville’s Bourbon & Beyond, a bourbon, music, and food festival headlined this year by John Mayer, Lenny Kravitz, Robert Plant, and Sting. And despite the theme, it’s open to anyone aged 5 and up.