No Tricks, Just Treats: Why October is our Favorite Month to Visit Maui

Maui is our happy place and our favorite island in Hawaii. We got married there in October and have gone every year since 2014.

After over a dozen trips—yes, we're basically part-time locals—we've discovered that while Maui is wonderful year-round, October is when she puts on her most charming outfit.

Here are all the adorable, quirky, and outright excellent reasons why you should book your next Hawaiian escape for the spooky, sunny season!

1. Elbow Room for Your Aloha Spirit

Not as crowded. Think of Maui's high season as a packed escalator—lots of beautiful people, but you're constantly bumping into someone's camera bag. October? It's like the escalator is moving at a leisurely pace, and you can actually stop to admire the view!

While the island doesn't exactly roll up its sidewalks, the sheer volume of visitors drops significantly from the summer frenzy and spring break rush. This means shorter lines for shave ice, an easier time snagging that perfect sunset table, and feeling like you have a little more personal beach bubble at your favorite snorkel spot. Your inner introvert will thank you!

2. Your Wallet Gets a Vacation, Too!

Prices are relatively cheaper! Let’s be honest: a trip to Maui isn't exactly a spontaneous Target run. However, traveling in the shoulder season of October is like finding a really good coupon code for paradise.

Flights tend to breathe a sigh of relief, room rates dip a delightful amount, and those pesky rental car prices aren't quite as aggressively priced as they are in March or July. While you'll still be paying for premium tropical bliss, you'll feel better knowing you scored a savvy deal. That little bit you save? Hello, extra mai tai!

3. The Ocean is an Absolute Gem

Snorkeling is great! We’re not going to lie; we’ve had a few trips where a rogue storm decided to stir up the waters like a giant ocean blender. But typically, October offers up some of the clearest, most dazzling water days of the year.

The water temperature is wonderfully warm (more on that later!), and the visibility for spotting those brilliant Humuhumunukunukuāpuaʻa (say that five times fast!) is usually spectacular. It’s like the ocean decides to polish its windows just for the October crowd. Grab your mask and prepare to hang out with some very colorful neighbors.

4. Pumpkin Patch with a View!

The pumpkin patch! Hold on, pumpkins in paradise? YES! Head up the slopes of Haleakalā to Kula and prepare for a view that will make your jaw drop. You can pick out a pumpkin with a sweeping, breathtaking view of the island, which is easily the most photogenic pumpkin patch in the world.

But the real, must-get, life-changing prize is the pumpkin bread at their general store. It is dense, moist, and tastes like a fluffy slice of autumnal heaven. It's the perfect quirky, non-traditional October treat that reminds you that Maui truly has everything.

5. The Great Whale Tease (and Promise!)

Whale Season starts! This one is pure quirky tragedy, but we've held onto hope for a decade! Every. Single. Time. we go, someone enthusiastically tells us, "Oh, you just missed the first whale of the season!" It's like Maui enjoys giving us a marine high-five followed by a gentle, ocean-sized slap in the face.

The migratory season for the majestic Humpbacks begins in late fall, and October is when those first few adventurous pioneers show up. Hopefully, you will be the lucky one who spots that first beautiful breach and can then, naturally, text us the news! (We'll try not to cry.)

6. The Weather Temp in Maui is Perfection

The best time of year to visit Maui island in October is because the weather is perfect. Forget the sweltering heat of August. October in Maui is that glorious, just-right temperature that makes you realize you were born to wear shorts and a lightweight linen shirt. While Maui is generally 79°F–89°F year-round, October seems to settle comfortably into the low 80s/high 70s, which is our version of atmospheric bliss.

And remember that warm ocean we mentioned? It stays so toasty that you can leave the bulky dive gear at home. The water is your second skin, and that, my friends, is pure vacation luxury.

7. The Road to Hana is a Dream Drive

Road to Hana is a great drive! If you've been hesitant about this iconic, winding drive, October is your time. The weather is generally sunny, the slight dip in crowds makes it easier to pause at those waterfall-laden stops.

Fewer cars means less stress and more time to truly soak in the bamboo forests, the black sand beach, and the sheer, stunning lushness of the eastern coastline. (Want to tackle the drive? Check out our complete Road to Hana guide here: https://www.thesweetestescapes.com/blog/best-stops-on-the-road-to-hana-maui-hawaii-with-map

8. A Hint of Holiday Sparkle!

Some Christmas decorations come out! Okay, we know it's only October, but if you love that tiny, early dose of holiday cheer, you'll catch a glimpse of it here. In late October, some stores start to put out a few festive touches. Seeing a Christmas lei or a string of lights twinkling against a backdrop of palm trees is the sweetest, most charming kind of holiday collision.

9. Pumpkin Crunch Ice Cream

Yup, couldn’t make it through a post without mentioning ice cream! At Island Cream Co, you must try their Pumpkin Crunch ice cream! It’s filled with pumpkin, cinnamon crumbles and roasted pecans! That says fall to me!

10. Maui Halloween Events

There are many Halloween events in Maui! Cannery Mall in Lahaina has activities and Trick or treating day of Halloween!

2025 events include Imua Keiki Halloween Festival at the Maui Arts & Cultural Center, a Halloween party at da Playground Maui, and the second edition of FUZZ FEST titled MUTATED MAYHEM!

The Hyatt Regency in Maui is hosting a Haunted House and Halloween movie night on Oct 30 and 31!

The Shops at Wailea -
Sunday, October 26 from 3-7pm at The Shops at Wailea Center-Wide Trick Or Treating | 3-7pm Participating merchants will be marked with balloons. Balloon Animals | 3-5pm Located in the Middle Valley in front of Rip Curl. Magic Show with Brenton Keith | 3:30 - 4:30pm A local favorite

Whaler’s Village in Kaanapali also has a movie night, activities, and trick or treating!

Speaking of kids and toddlers, check out my top 10 things that I bring for every vacation with the kiddos! You won’t want to miss these toys or snacks: https://www.thesweetestescapes.com/blog/10-things-toddler-travel

So there you have it! Maui in October is an absolute dream—a little less busy, a little more budget-friendly, and all the gorgeousness you expect from the Valley Isle. Trust us, it’s the Goldilocks month for Hawaiian travel: just right.

Have you ever visited Maui in the fall? Share your favorite memory in the comments below!