Photo: WEILL Associates

The Best Places to Travel This October

Travel Insider Guides
by Matthew Meltzer Aug 16, 2019

October was once the month that brought the first chills of winter. When leaves began to change and we started pulling our sweaters out of storage. But it seems the last few years we’ve seen an unusually large number of people in cold-weather destinations posting pictures of themselves in shorts, enjoying a rooftop cocktail in late-October Toronto.

You can look at this a few ways. First, as an alarming realization that something is definitely off with Earth’s climate. Or as an opportunity to visit even more places in October, since concerns over “snow” and “pants weather” aren’t really a thing. We prefer to think the latter (since the former sends us into a depressive spiral) and offer up these dozen destinations as the best places to travel in October this year.

1. Austin, Texas

Photo: Ismael Quintanilla III/Shutterstock

Outside of South by Southwest, October is far and away the craziest time of year to hit Texas’s capital city. Austin City Limits — probably the fall’s biggest music festival — runs from the 4th to the 6th, this year headlined by Guns n’ Roses and Childish Gambino. Culture continues to dominate the scene later in the month as the Texas Book Festival brings one of the biggest literary festivals in the country to town from the 26th to the 27th. And the Austin Film Festival hosts over 175 screenings, roundtables, and industry events the last week of the month.

For sports, there’s the religious experience that is University of Texas football, which hosts Kansas on the 19th. Plus the Formula 1 United States Grand Prix at the end of the month, bringing European auto racing chic to the heart of Texas. And if you’re up for a little road trip, the Texas State Fair is only a few hours away in Dallas.

2. São Paolo, Brazil

Photo: Will Rodrigues/Shutterstock

Art lovers around the world will be making their way to São Paolo this October, as it hosts the 33rd Bienal de São Paolo. This art biennial is the second largest in the world behind the original in Venice, Italy, and will showcase 12 individual artist shows and six group projects, as it runs from September into early December. The show actually travels to eight cities before landing in its home at Ibirapuera Park, where over three-quarters of a million people will visit during its run.

Beyond the art festival, São Paulo offers plenty to do, from exploring the city’s famous Beco de Batman (yes, that Batman) art-covered street to bike riding down the Avenida Paulista. São Paulo is also a great base for diverse day trips to places like seaside Santos, verdant São Roque, and colorful Embu das Artes.

3. Winston-Salem, North Carolina

Photo: Nature Lovin’ Geek/Shutterstock

Generally, the Piedmont Triad is not thought of as a prime leaf-peeping destination. But a trip to the Blue Ridge Mountains this time of year is stunning for foliage lovers, without having to deal with the traffic of the Mass Pike. ln Winston-Salem, the foliage season lasts a little later here as fall temperatures don’t dip into color-changing levels until the final weeks of the month. You can enjoy the leaves from one of the region’s 45 wineries, which’ll be hosting pairing dinners, vineyard hikes, and grape stomps as part of their October harvest season.

Trekking with llamas more your thing? No problem! Save yourself the plane ticket to South America and trek through the fall colors with a pack of friendly llamas. Divine Llama Vineyards offers wine tasting with its two-mile treks, possibly the most unique wine-tasting experience in America. And much better than just driving around pointing at leaves.

4. Alberta, Canada

Photo: Songquan Deng/Shutterstock

Does it get a little cold in the Canadian Rockies come October? Maybe, the climate change jury is still out on that one. But the skies will definitely still be brilliantly dark for the annual Jasper Dark Sky Festival, which takes over Jasper National Park from the 18th to the 27th. Here you’ll listen to the Edmonton Symphony Orchestra serenade the stars, take a tram ride a full kilometer closer to the sky, and possibly see the northern lights during their earliest appearances.

Elsewhere in Alberta, the Rocky Mountain Wine and Food Festival happens in Calgary on the 18th and 19th. Cinephiles can get their Canadian Cinema on at both the Edmonton International Film Festival from September 26 to October 5, and the Banff Centre Mountain Film and Book Festival from the 26th to November 5.

5. New Jersey

New Jersey is the new Dubai. Don’t believe us? Venture to the East Rutherford on October 25 and behold the most impressive indoor entertainment complex this side of the Persian Gulf when American Dream finally (a version of the project was first proposed in 2003) opens its doors. The three-million-square-foot complex will include North America’s largest fully enclosed Dream Works Water Park, as well a Nickelodeon Universe park so families can escape here even when it’s not theme park weather.

“Oh, but where’s the indoor ski slope?” you say. American Dream’s got it, a full 16-story ski and snow park perfect for skiers who don’t like snow chains. It’ll also include an Angry Birds mini-golf course, a 300-foot observation wheel, a performing arts center and a Legoland discovery center. Plus an NHL-sized ice rink, in case the Devils need a new spot to practice. All it’s missing is a 150-story tower next door, and it basically saves you a 17-hour flight to the UAE.

Once you’ve got all the thrills out of the Meadowlands as you can handle, resist the temptation to extend your trip to NYC and head to nearby Monmouth and Ocean counties in Central Jersey instead. October is a favorite time of the year for locals, when you can find quality pumpkin and apple picking at farms all over, as well as corn mazes, family-friendly hayrides, and scarier haunted ones at night for teens (and adults who still spook easily). Shore towns like Asbury Park and Point Pleasant are also devoid of tourists, and the surf is the best it gets year-round.

6. Laos

Photo: BTWImages/Shutterstock

Laos isn’t particularly over-touristed. At least not yet. But if there’s a sweet spot to hit it when the weather’s tolerable and nothing even resembles a crowd, it’s October. This month marks the end of “green season,” which as the name might imply means the tropical foliage is at its fullest, and trekking through the mountain jungles, the limestone caves, and the Plain of Jars is particularly photogenic.

October also marks the end of the three-month Buddhist Vassa, an annual retreat where Theravada practitioners are restricted to their temples. Their return to public life is celebrated with offerings and food, and it coincides with the Boun Suang Heua boat racing festival in Vientiane. Teams from all over Laos race down the Mekong, and the festival along the shore is awash with street food, music, and floats. If this all sounds like your dream southeast Asian vacation but you’d rather not deal with planning it, InsideAsia tours run a Northern Laos Expedition that hits all of this and Luang Prabang starting at $3,211.

7. Natchez, Mississippi

Photo: italianestro/Shutterstock

If the sweltering humidity of summer was all that was keeping you from discovering the otherworldly southern-ness of Natchez, Mississippi, October is your time to get down there. Not only has the weather turned into a mild riverside chill, but it’s also when the city hosts its annual Natchez Balloon Festival from the 18th to the 20th. One of the largest festivals of its kind in America, it’ll also showcase live music, local restaurants, local artists, and a full-fledged midway carnival.

Additionally, October is the lone time of year you can traipse through dozens of the remarkable antebellum homes that still stand in Natchez. During the Fall Pilgrimage, mansions that aren’t usually open to the public let the people in, and you can see how they’ve painstakingly restored the townhomes of Victorian-era southern aristocracy.

8. Belize

Photo: Aleksandar Todorovic/Shutterstock

Belize might not have the full-fledged tourist saturation of some other Caribbean destinations, but the 174 miles of unspoiled coastline and second-largest barrier reef in the world can still get a little crowded during summer. October, however, is the slowest of the slow season here, meaning you’ll have spots like the Great Blue Hole and the ruins at Caracol all to yourself.

Hotels are insanely cheap this time of year too. Case in point: The 400-acre eco-luxe Lodge at Chaa Creek has deals for $99 per person per night. Or the Banyan Bay Suites, which are chopping 40% off room rates with multi-bedroom suites starting at $210 a night.

9. Sayulita, Mexico

Photo: Allison Michael/Shutterstock

Dia de los Muertos in Mexico has become an “it” trip the past half-decade or so. But do yourself a favor and avoid going to Oaxaca like every other person who has no cultural ties to the festivities and encroaches on the locals’ celebrations for their Instagram feed. Instead, venture to less-visited Riviera Nayarit and the busting surf enclave of Sayulita. The town still maintains much of its bohemian charm, and from the 31st to November 2, you can experience Day of the Dead here without being too bothersome or adding to an army of cell phones. Catch the traditional night walk, marvel at the street decorations, pay respects to the oferendas, then retreat to the beach to enjoy some waves.

10. Kenya

Photo: Sergey Novikov/Shutterstock

If you’re looking to travel with a little bit of purpose this October, might we suggest heading out on a big-game drive through Kenya? Kin Travel — a company whose mission is as much about conservation and community improvement as it is guest experience — is running its most luxurious trip of the year with a weeklong adventure to Cottar’s 1920’s Camp.

During your stay at one of the world’s most sustainable hotels, you’ll go on morning and evening game drives, take a morning bush walk with park rangers, and even have lunch with a reformed poacher. But beyond spotting wild animals you’ll also visit a Massai Warrior school and local market, as well as spend some quality time in an Olderkesi village, which gets direct investment as part of your trip cost.

11. Lavaux, Switzerland

Switzerland’s largest contiguous wine region hits its peak in October, when the 19,000 acres of vineyards on the hills overlooking Lake Geneva turn fabulous shades of orange, red, purple, and yellow. Hike and taste wine through the small towns and vineyards dotting the hillsides before retiring to the Beau-Rivage Palace, set on 10 acres in Lausanne at the foot of the Alps. They’ll also take you on a tour of the vineyards in a vintage car, then visit chocolate and winemakers throughout the region.

You can also stop into Anne-Sophie Pic, a two-Michelin star restaurant with over 75,000 bottles of 3,000 different wines. There, Chef Anne-Sophie — who has three stars herself — will craft a glorious meal paired exclusively with Swiss wines.

12. Key West, Florida

Photo: Fantasy Fest/Facebook

There are still a few places left in the world where it’s probably best you leave your phone at home. Fantasy Fest is one of those places. The annual Key West Halloween shitshow brings us all that is great about Florida, from drag queens to leather-clad bikers, outlandish costumes, swingers, and clothing-optional celebrations. It’s an anything-goes street party that’s a little like Mardi Gras without the rules, or Woodstock with warmer weather.

Clothing is in short supply, though not everyone walking down Duval Street during the annual parade is someone you’d necessarily want to see naked. But it’s Fantasy Fest, so there’s no room for judgments and even less room for social-media posting. It’s truly a what-happens-here-stays-here destination and a must-visit for anyone within driving distance of Florida.

Discover Matador

Save Bookmark

We use cookies for analytics tracking and advertising from our partners.

For more information read our privacy policy.