Our Top Picks For Fall Travel This Year

fall vacation

Unsplash/Rula Sibai

Planning a fall vacation? Regardless of whether you’re coming from New York or California, we have some ideas for where the next few months could take you.

And don’t forget your extra few days off around Thanksgiving. That gives you the opportunity to jet farther around the world — if you don’t mind missing the family turkey dinner, that is. There are both international destinations and places right at home in America that make for prime autumn retreats. Check out our picks for fall vacation spots.

1. Chicago, Illinois

fall vacations

Unsplash/Erol Ahmed

We love the Windy City, and the fall is the ideal time to wander through the Midwest’s biggest metro. The brutal winter is still a few weeks (hopefully months) away, so you can enjoy walks along Lake Michigan’s Navy Pier. Charming tree-lined neighborhoods like the West Loop (eat at The Girl and The Goat) and Lincoln Park (get deep dish pizza at Pequod’s Pizzeria) offer plenty of laid-back options while still giving you big city vibes.

2. Chiang Mai, Thailand

fall vacation


The rainy season comes to an end in Thailand at the end of October, making it a pretty good fall destination in November before the tourists start to crowd in for U.S. wintertime. Chiang Mai, the largest city in northern Thailand, offers delicious food, unmatchable architecture and the opportunity to visit elephant sanctuaries and interact with the gentle giants.

3. Ozark National Forest, Arkansas

fall vacation

Flickr/Marco Becerra

We’ll be honest — we hate the phrase “leaf peeping” (who thought of this?!) but we’re gigantic fans of fall foliage. If you want endless views of fall colors, we’d suggest a trip to the Ozarks. It’s a large region, covering parts of Arkansas, Missouri, Oklahoma and Kansas. The hills are higher in Arkansas, so you’ll have great vantage points. Try Eureka Springs for some artistic flair and a historic downtown Main Street.

4. San Miguel de Allende, Mexico

fall vacations

Flickr/Christopher Michel

Do you want your fall vacation to look like the Pixar movie “Coco” or as close as you can get in reality? Then we’d suggest visiting San Miguel de Allende. There are endless shops filled with handmade artisan crafts, historic architecture and brightly colored decor when the season gears up for the Day of the Dead. Seriously, it’s a weeklong party here.

5. Ithaca, New York

fall vacations

Flickr/Lost In Fog

Further up in New England usually takes the cake for fall foliage bonanzas, but we like Ithaca’s plethora of cozy fall activities. We vote for hiking along the nearly 150 waterfalls in 10 miles, followed by sipping drinks from local breweries and wineries. And that’s not even mentioning the annual Apple Harvest Festival. Hello, apple cider donuts and other farmers’ markets delicacies!

6. Marrakesh, Morocco

fall vacations

Unsplash/Annie Spratt

When the summer heat eases its grip on Morocco, you want to head to the amazing country. That’s late September and October, but don’t worry — the weather still will be warm. Browse Marrakesh’s mazelike souk, Jemaa el-Fnaa, a marketplace with every souvenir you can imagine. And since the weather is cool enough for long exploration walks, take a gander through the Koutoubia Mosque and Bahia Palace.

7. Telluride, Colorado

fall vacation


The town of Telluride is spectacular, with alpine backdrops to the adorable Victorian-era town. It’s not far from Aspen, the playground of the luxe travel set, so you can expect million-dollar views. But there’s one must-do activity that won’t cost you a cent with the same panoramas: the Telluride/Mountain Village gondola. It’s a free 13-minute ride up into the San Juan mountains with 360-degree views of the surrounding autumn splendor.

8. Tallinn, Estonia

fall vacations


Europe’s latest favorite fairytale is all the way up north, so go early if you want to catch some green leaves giving way to yellows, reds and golds. The Old Town is giving us straight-up castle vibes (make sure to visit the actual Toompea and surrounding grounds). It’s so charming that we wouldn’t blame you if you want to linger a little while until Christmas market season gets going.


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