Whether you’re looking forward to all the fall festivities or the slightest thought of a chill makes you want to go into full-on hibernation mode, one thing’s for certain: October is packed with plenty to do, and that extends to travel experiences both near and far. There's the end of harvest and the start of Dia de Los Muertos, or “Day of the Dead,” celebrations that make Halloween look like child’s play in Mexico, while Oktoberfest pretty much takes over the rest of the world. This month’s destinations are particularly great for budget travelers who are saying goodbye to the smoldering summer heat but aren’t quite yet ready for the blistering winter cold.
The Best Places to Visit in October
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Published Jul 6, 2023
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Here’s How We Picked the Places
We looked at both the new news and weather in each individual location and what was happening locally in each place, too, including events, concerts, activities and cultural experiences. Finally, we layered over some data from airfare booking platform Skyscanner, comparing flight prices from everywhere across the USA in the month of October. We also looked at lodging pricing in each location from Vrbo, Airbnb, and other hotel search platforms including Expedia and Kayak to help reveal the very best deals for you. And finally, we sprinkled in some anecdotal knowledge of what jet-setting readers like you will absolutely love this month.
1. Sleepy Hollow, NY
- Why We Recommend It: Spooky scenes and small town vibes, architecture and historical tours, excellent outlet shopping nearby
- Where to Stay: Tarrytown House Estate on The Hudson (from $265/night), Well-Appointed Suite with Privacy (from $122/night), Westchester Marriott (from $290/night)
October marks the start of the spooky season, and if you've never experienced the charms of Sleepy Hollow and nearby Tarrytown, you are seriously missing out. The world-famous cemetery of the same name is legit one of the coolest/creepiest places you can visit in the U.S. — it's hauntingly beautiful and a great way to spend an afternoon seeing the famous graves of Andrew Carnegie, William Rockefeller, Elizabeth Arden, and of course, Washington Irving, the author of The Legend of Sleepy Hollow and Rip Van Winkle.
Other top experiences to consider are viewing the more than 7,000 illuminated pumpkins at The Great Jack O'Lantern Blaze, hayrides and apple picking at any of Westchester County's nearby orchards and farms, and a visit to the gorgeous and exquisite Lyndhurst Mansion. Dreamed up by architect Alexander Jackson Davis and overlooking the Hudson River, this Gothic Revival mansion is celebrated as one of America's finest historical homes. The massive 67-acre grounds are also ideal for snapping some pics in your sweater weather best and officially transitioning your IG grid entirely to fall vibes. Pro tip: When you make the Sleepy Hollow area home base, you're also a quick ride from the incredible shopping at Woodbury Commons Premium Outlets. This shoppable destination meets a walkable village, is lovely on a warm fall day, and you'll be hard-pressed to find a brand there you wouldn't want to shop for. It's also home to premier outlet department stores like Saks Off Fifth and even high-end designer outlets like Gucci, Saint Laurent, Lanvin, Prada, and more which offer everything at frequently steep discounts.
2. Lake Como, Italy
- Why We Recommend It: Excellent airfare deals, romantic vibes, lakeside aperitivo moments crafted by master mixologists
- Where to Stay: Apartment in Bellagio (from $224/night), Beautiful Lake Como Condo with View & Pool (from $226/night), Hotel Villa Flori (from $614/night)
Direct flights into Milan can be had for as little as $404 in October, according to Skyscanner, and once you’re there, you’re a quick 90-minute drive into the Italian paradise of Lake Como. It’ll also be shoulder season at the reverse-Y shaped lake, meaning you’ll find deals at many glamorous hotels, Airbnbs and Vrbos.
To intimately know Lake Como is to explore these many historic properties and their botanical gardens which line the shores, each statelier than the next. Passionistas of the Italian villa variety can walk right into Villa Monastero or Villa Carlotta like you own the place. Those who want to splurge and have the full experience should investigate a stay at Villa d’Este or Passalacqua. But we also love a hidden gem hotel, like Hotel Villa Flori, nestled along the shoreline. It’s a romantic getaway for couples seeking a glamorous retreat from the hustle and bustle of everyday life and accommodations are exceptionally bike-friendly, with the resort offering a secure bike room plus customized bike outings.
In October, you can also score other deals on romantic, fancy pants activities in Lake Como. A fall boat ride on the lake is always a good idea, and simply indulging in a traditional Italian eatery housed in an aristocratic villa. At Ristorante Raimondi, Chef Marco creates meals that harken back to some of the oldest and most famous dishes in Italy, including doppio entrecôte, controfiletto d’agnello, and tiramisù scomposto. After dinner, lovers are invited to share a drink at the iconic Lounge Bar, where cocktails are crafted to individual tastes and served alongside a dazzling vista of the lake and mountains.
3. Madeira, Portugal
- Why We Recommend It: Breathtaking landscapes, outdoor adventures, vibrant culture, world-renowned wine
- Where to Stay: Quinta da Bela Vista (from $197/night), The Vine Hotel (from $208/night), Savoy Palace (from $290/night)
A secret gem nestled off the coast of Morocco, the Madeira archipelago in Portugal is the wise choice for those looking for an understated destination chock full of beauty. Until recently, the area was challenging to access, and even residents struggled through steep mountain trails. But Madeira is officially up and coming, and thanks to new roads and highways, it's easier than ever to check out the islands that make up this slice of paradise!
Trip Advisor declared Madeira as a must-visit location of 2023, and it's easy to see why: A rich tapestry of cultural traditions, mouthwatering and super healthy gastronomy (the best combo if you ask us!), and exhilarating outdoor escapades will keep you busy all day long. At sunset, it's time to settle in and sip some internationally renowned wines while you indulge in breathtaking vistas. The October weather in the archipelago is mild and pleasant. That's right: with temps in the 60s, there will be plenty of time spent outside enjoying some of the best of this Europe-meets-Africa beauty.
Hiking through the Levadas is a can't-be-missed activity. These historical irrigation canals used to bring water from the north slopes to the south, and they're now picturesque pathways for hikers to indulge in the freshest air, some next to stunning waterfalls and lagoons. Thrill-seekers should Embark on canyoning adventures through the island's mountains, descending through waterfalls and exploring hidden gorges. A trek through the UNESCO World Heritage Site of Laurisilva Forest reveals the island's pristine and ancient forests. Surfing is also becoming increasingly popular in the islands, and it's noted for being a crowd-free place to rip waves.
Next on your hit list? Hop on a Jeep tour to the West Side, where you'll discover even more amazing views and visit many different villages to experience local culture and traditions. Take a boat tour in Porto Moniz along the North Coast to check out striking cliffs, natural pools, and crystal-clear waters. Funchal is the capital of Madeira and arguably its "biggest" town, full of religious sites such as Sé Cathedral; it's also where you can enjoy more views from the Monte Cable Car and the stunning gardens at the Monte Palace. And since you're in Funchal, why not enjoy the exhilarating toboggan aboard a traditional wicker sled or Monte basket car descending the steep streets of Funchal?
4. Orlando, Florida
- Why We Recommend It: Fall-themed events, Halloween galore, endless entertainment
- Where to Stay: Orlando World Center Marriott (from $169/night), Four Seasons Resort Orlando at Walt Disney World (from $1,621/night *with special Halloween pricing), The Grove Resort & Water Park Orlando (from $207/night)
Orlando might be the spookiest place to indulge in a Halloween scare for people of all age groups. The city is packed with activities all year round—hello, theme parks!— but the fun most people forget about is well beyond those park gates. Haunting Nights is just one example, a Creative City Project designed to bring art and excitement to the forests of Leu Gardens! You can grab some beers in the Ivanhoe Park Brewing Co.'s parking lot, where lawn chairs, blankets, and everyone's favorite Halloween movies complete the experience every Friday.
For an Oktoberfest celebration, head straight to Avalon Park on October 14th for the annual celebration with plenty of beer, live music, and alpine-style dancing! The Fall Festival at Southern Hill Farms includes delicious eats like apple ciders, donuts, and s'mores, and spots like Whisper Creek Farm also host corn mazes and pumpkin carving. For a dose of culture, visit the Orlando Museum of Art, where you can admire an impressive collection of contemporary and classical works. Then, stroll through the picturesque Leu Gardens, known for stunning botanical displays and a peaceful ambiance, which we can all use occasionally.
If you can't pass, go to Orlando without hitting a park, there are many Halloween-themed haunts there in October, too, like Universal Orlando's Halloween Horror Nights—but beware! Horror Nights is not an event catered to children. It does include ten haunted houses and five scare zones designed to terrify even the biggest horror fans. You can find a more classic family-friendly Halloween experience at Walt Disney World at Mickey's Not-So-Scary Halloween Party. Aside from the quintessential Disney park firework experience, you can take your kids trick-or-treating during the kid-friendly party!
5. Maui, Hawaii
- Why We Recommend It: Top-tier culinary experiences, world-envied beaches with white, red and black sand, prime whale watching opportunities
- Where to Stay: The Westin Maui Resort & Spa ($981/night), Kā'anapali Beach Hotel ($392/night), Condo with Amazing Views (from $185/night)
There's no need to convince anyone that Hawaii is a paradise on Earth, and October in Maui is unmatched! It's when the island comes alight with the highly anticipated Hawaii Food & Wine Festival. The three-day belt-buster is held at the picturesque Kā'anapali Beach Resort, where you'll taste the best Hawaiian cuisine through a series of events with delicacies crafted by the hands of culinary geniuses such as Bonny Davis, Brady Ishiwata Williams, and Michael Lofaro. It would be best if you also came ready to sip the best Italian wines, with a curated selection by a Master Sommelier, and fireworks will top off this incredible food-fest-meets-beach-party.
Throughout Maui, there's a bounty of activities for nature lovers: snorkeling, sunset sails, and zip-lining are just some of the most popular. With an average high of 77, October is the ideal time to hit Maui's miles of hiking trails since it's not too hot to enjoy. The Pipiwai Trail — one of the best hikes on the island that ends in the 400-foot Waimoku Falls — can sometimes feel steep, but the view is well worth it. Another mesmerizing experience is the 5.7-mile Kahakapao trail in the Makawao Forest! Experienced hikers will appreciate the hike at the Haleakala National Park. Volcanic landscapes sculpt the park and are renowned by bird watchers. Conservation is the heart of their mission, too, and you'll leave the area more in love with Hawaii's thriving natural life.
Though a tropical island, Maui also has some unique fall fun, best enjoyed at the Kula Country Farms pumpkin patch, which offers breathtaking bi-coastal vistas and many pumpkins. There are Halloween crafts, animal farms, and even a corn maze. Meanwhile, "Halloween in Lahaina" is a street festival that draws crowds of 20,000 people so that folks can enjoy live entertainment, food booths, and a costume contest!
6. Okinawa, Japan
- Why We Recommend It: Vibrant festivals, stunning beaches, warm hospitality, bike friendly
- Where to Stay: The Beach Tower Okinawa (from $350/night), Ala Mahaina Condo Hotel (from $160/night), Cottage to Chill in Sun, Sea & Greenery (from $149/night)
Okinawa is a treasure trove thanks to its refreshing culinary scene, rich culture, and natural beauty, thanks to its complex history. Okinawa was annexed to Japan in the 1600s, but the area's proximity to China and Taiwan makes Okinawa feel like you're stepping into a whole new country within Japan. Revered for its white sand beaches and crystal-clear water, October is a particular time in Okinawa, as the weather is just right: not scalding hot and not rainy or cold.
During this time, visitors can take in the incredible cultural experience of the Iriomote Island Shichi Festival, a 500-year-old celebration of harvest on Iriomote Island, an isolated area of Okinawa.
During the festival, villagers give thanks for the quality of their crops and wish for a bountiful one ahead with lion dances, stick fights, and captivating performance art to admire.
Towards the end of the month, step back in time and embrace the historical grandeur of Shuri Castle. Evoking the spirit of the Ryukyu Kingdom, the reigning monarchy before Japan's annexation, it is celebrated with 6,000 lights to illuminate the gorgeous castle, not to mention several parades. You can also experience traditional Ryukyuan arts, crafts, and performances or marvel at the colorful costumes used by Ryukyu's nobility. All around you, you'll hear the dynamic drums that are a distinct mark of the Okinawan music styles.
You might have pinned The Blue Cave on your Pinterest travel inspo board for a good reason. The cave can be explored by diving and snorkeling, and night rides are also offered. Are you looking to get away from the crowds? Check out Mibaru Beach on the island's south side, which is never packed with tourists but still easily accessible. Of course, this is Japan—so knowing what's on the menu is necessary. Yama no Chaya Rakusui, located in Nanjo, has drop-dead gorgeous views of the beach, and their entire ethos is about relaxation, with quality vegetarian grub to boot. Try their Gemai Gozen set and sample some of the best traditional Okinawan vegetarian food. Soki Soba is another unmissable Okinawan noodle dish topped with tender pork ribs and flavorful broth—head to Hamaya Soba to try it for yourself! If you have a sweet tooth, look out for the Chinsuko, a traditional Okinawan cookie that's sweet, crumbly, and perfect with a cup of tea or as a souvenir to bring back home.
7. Cancun, Mexico
- Why We Recommend It: Bustling nightlife, tons of outdoor adventures, great food, nearby Day of the Dead festival
- Where to Stay: Hotel Xcaret Mexico (from $611/night), Grand Fiesta Americana Coral Beach (from $588/night), Ocean View Two-Story Penthouse (from $255/night)
Dirt-cheap fares put the ’Cun at the top of our list this month when “rainy season” means you may see a cloud or two during the day. What that also means: Plenty of time still to enjoy the pool (and its swim-up bar), jet skiing or parasailing along the coast or spending a rather wild night out at one of Cancun’s many popular nightclubs. Whether it’s your first time or one of your favorite fly-in-for-the-weekend spots, it’s never a bad idea to organize a tour or simply hire a taxi for the day to take advantage of the region's incredible cenotes—natural sinkholes formed by a collapse of limestone that reveal gorgeous aquamarine water ripe for jumping and swimming in. During October, especially toward the end of the month, many resorts offer Day of the Dead cultural experiences. One of note and authenticity is the annual Day of the Dead festival, Festival of Life and Death Traditions, that happens in Xcaret Park, roughly a 75-minute drive from Cancun. It features concerts, ofrendas (or paper flower) making activities, guest artists, and even access to Mayan healers, plus a whole lot of food.
Speaking of eats, back in Cancun, we recommend La Destileria and Tacun for authentic grub, and the immersive video dining experience—where the table you sit at is a giant video screen that is paired to take you through a multi-sensory, multi-course meal celebrating Mexican food—at La Joya. And while there are plenty of yummy Mexican bites to be had, when you’ve officially had your fill of chips and guac, consider splurging on Le Basilic, one of Cancun’s most celebrated French fine dining spots.
