Things to Do on Maui in October

September 26, 2018  •  1 Comment

Things to Do on Maui in October

Celebrating Halloween on the world-famous Front Street might be one of the biggest draws for visiting Maui in October.


But the autumn month is about far more than costumes and the Pacific’s iteration of Mardi Gras: Savvy travelers know that October means sparser crowds, cheaper accommodations, quieter flights—and just as much excitement as July.


Whether you’re Maui-bound this fall—or just dreaming up your idyllic holiday—here are 9 fresh ways to spend your island days:


Brunch at Paia Inn + Twin Falls

The leeward side’s tony resorts and posh landscaping are nothing short of spectacular (more on that later), but for a taste of the island’s carefree life, head to Paia. Often called The Windsurfing Capital of the World,” this former plantation town may have gone through major gentrification in the last decade but it still holds its kick-back surfer ethos. Enjoy its soul over cardamom French toast at Paia Inn, where the staff has been voted some of the lustiest in the world and Owen Wilson frequently stops in. After a walk along Baldwin Beach—where you can search for shells and see the stunning crags of the central coastline—stroll through a lush jungle on your way to Twin Falls: a pair of cascades just off Hana Highway.


Haleakala Sunrise + Spa Grande

No trip to Maui is complete without exploring the eastern bulwark that makes up three-quarters of the island. With a name that translates to “House of the Sun,” Haleakala has been the inspiration behind Mark Twain’s prose, Jack London’s essays, and myriad Hawaiian cultural practices (to natives, it’s considered the realm of the gods). At dawn, the summit—10,023 feet above sea leveldoes seem to hold the sun as it crests in splendid, otherworldly colors. See it with one of the top Haleakala tour companies on the island, Skyline Hawaii, whose sunrise and sunset tours include journeys through the neighboring towns, fascinating facts, and amusing camaraderie. Then, unwind from the early-a.m. wake-up call by spending the rest of your day lounging in luxury at the Grand Wailea’s Spa Grande. Here, you’ll find 50,000 square feet of opulence that include Roman-style baths, body care treatments, and a lomi lomi massage that incorporates healing Hawaiian plants.


Turtle Town + Willie K at Mulligans on the Blue

Otherwise known as honuHawaiian Green Sea Turtles are an emblem of Maui in themselves: gentle and giant (as in 3-5 feet long and up to 700 pounds), these beauties are the most common of the seven turtles found throughout Hawaii, and are frequently seen basking, swimming, and snacking in the waters off Makena. Hence the name the spot has acquired in recent years as “Turtle Town,” a section of the Pacific, favored by these goliaths, south of Kihei. Come early and beat the crowd with Kai Kanani’s signature Deluxe Snorkeling Tour at Molokini Crater then soak up the sun before the notorious Makena Cloud sweeps in. Wednesday evenings on the south side have become synonymous with the Willie K Dinner Show —a dazzling weekly event, held at Mulligans on the Blue, that features Grammy Award nominee and Maui-born musician Willie K. Arrive early for Shepherd’s pie and an Irish beer before the performance, then kick back as this local boy sings opera, cracks jokes, impersonates Michael Jackson—and plays the ‘ukulele like no other.


Dig Me Beach + Hawaii Food & Wine Festival

Lovingly dubbed Dig Me Beach, Ka’anapali Beach—the waterfront that rests in front of the West Side’s resort strip—has rightfully earned top honors on Best in the U.S. (and Best in the World) lists. Over a mile long, capped with glorious blonde sand, and featuring some of the best swimming opps on the island, this buzzy beach is indeed one for the books. Snorkel, sunbathe, people-watch, chill—and perhaps take a dive off the west end’s Black Rock—before rocking your finest for the Hawaii Food & Wine Festival. The annual, all-star event takes place around all the major islands in the Aloha State; Maui’s version, Global Street Food, presents over a dozen culinary masters from around the world, gourmet food, craft cocktails, boutique beers, and terrific wine.


Wai‘anapanapa State Park + Charles Lindbergh’s Grave

Rise before the birds and set out for the Road to Hana—a serpentine journey (and inarguably one of the most scenic drives in Hawaii) that takes you across stone bridges, past towering waterfalls, and over windswept bays. Frequent stops are irresistible; to truly stretch your legs, plan to spend a few hours at Wai‘anapanapa State Park. Here, you’ll find a beach comprised of onyx sand, a lichen-filled grotto steeped in Hawaiian myths, a natural sea arch, and a blowhole. After stopping in Hana for chili and rice at Hana Ranch Store (and a dip in the ocean at Hamoa), find your way to Charles Lindbergh’s grave in Kipahulu—the famous aviator is buried at one of the oldest churches in Hawaii.


Maui Golf & Sports Park + Maui Chef’s Table


No matter if you’re traveling with keiki or visiting with your college crew: Maui Golf & Sports Park delights any and every age with their mix of bumper boats, miniature golfing, rock climbing—and an X-treme Trampoline that’ll leave you, well, jumping for joy (as in 30 feet in the air). Best part yet? The entertainment center is set outdoors, allowing you to savor October’s brilliant rays and views of Maalaea Harbor. Come nightfall, head to the Maui Tropical Plantation for an event that will linger for decades: Held on select weekend nights, Maui Chef’s Table was conceived by ‘Aipono award-winning chef, Jeff Scheer, who wanted to pair fun-loving, communal dining with an open kitchen, the island’s freshest ingredients, and talking story. The result? One of the most coveted dining experiences on Maui, wherein Scheer and/or his carefully-selected team prepare a multi-course meal that encourages conversation and questions between cook and patron. The food is exquisite; the views—of the plantation’s verdant grounds, the Pacific in the distance, and the West Maui Mountains—add to the romance.


Kealia Pond National Wildlife Refuge & Maui County Fair

There are many things to do in Kihei, including in North KiheiKealia Pond National Wildlife Refuge holds a number of claims to fame: it’s one of the last remaining natural wetland habitats in Hawaii. It boasts 700 acres. It’s considered home to 31 species of birds and waterfowls, including the Hawaiian Stilt and the Hawaiian Coot. It provides shelter for the endangered Hawksbill Sea Turtle. But you wouldn’t know it driving by: the modest though lovely area is often quiet, rendering a stroll along its boardwalk a tranquil way to enjoy what’s left of fall. Contrast it all with a night on the town—Kahului Town, that is, where the 96th Maui Fair will be in full flourish. Here, you can snack on Filipino donuts, eat cotton candy, ride on a Ferris wheel, shop Maui-made products—and see an orchid exhibit that’ll blow you away.


Launiopoko + Halloween on Front Street

The waves and wind on Maui’s North Shore may be picking up this time of year, but a few good days of pleasing waves still roll into the leeward coast. One of the choicest spots to learn how to hang (as in ten) is at Launiopoko on the way to Lahaina. With three breaks, calm swells, excellent views, and a shallow bay for keiki to play, it’s a popular place for those who are still green on their boards. Rent yours from Boss Frog’s (they’ll even deliver it to your condo or resort) or book a private lesson. Refuel at Aloha Mixed Plate—their ono grinds, all at economical prices, earned them the 2017 ‘Aipono award for the island’s “Maui-est” restaurant—before donning your mask for the wild and wonderful Lahaina Halloween Party. One of the most popular events in Hawaii, the annual extravaganza lures 30,000 people from across the globe, with its parade, street-festival, music, dancing, and, score, $1000 prize for best adult costume. Prepare yourself for astonishment: countless kama’aina start planning their (often outrageous) get-ups on November 1st.


Helicopter Tour + Wailea Progressive Dinner

Exhilaration meets awe on Blue Hawaiian Helicopters’ island tours, which take flyers to Maui County’s secret gems—from the gem-green forests of Hana and the world’s tallest sea cliffs on Molokai to the lunar-esque basin of Haleakala. Guides provide fascinating exposition (as Frommer’s reports, they’re “part Hawaiian historian, part DJ, and part amusement-ride operator”) while the helicopters themselves—high-tech, top-of-the-line Eco-Star crafts—blend luxury with comfort and safety. For the ultimate experience, ensure that your tour will take you close to the Wall of Tears—seventeen slender waterfalls in the depths of the West Maui Mountains. Once you’ve come down—literally and figuratively—head to Wailea for a progressive dinner. Otherwise known as a safari supper, these ultra-fun meals—at least when spent at restaurants—include grabbing entrées at different venues. Start with an artisan cocktail at the Andaz’s super-sultry (and poolside) Lehua Lounge, bounce over to Spago in the Four Seasons for one of their famed ahi tuna poke cones, dig into a rack of lamb with Maui pineapple jam at Nick’s Fish Market in the Fairmont Kea Lani, then end it all with port wine and chocolate soufflé at the Marriott’s Humble Market Kitchin. Sauntering down the Wailea promenade is half the fun, while Maui’s starlit, palm-framed sky is pure magic—in October, and always.


Get Married on Maui!


There are many reasons why Maui is a world-famous wedding destination.  Tropical landscapes and great weather are a start, but reducing a guest list (and cost) by having a small beach wedding can relieve many headaches.  Or, if you want to give your family and friends a reason for vacation, have a large estate wedding. Anyway you dice it, a wedding on Maui is unforgettable.  That being said, having remarkable wedding photos to capture the event will help you and generations of loved ones cherish the memories for all time.   Dustin Thompson Photography has shot everything from real estate photos to maternity, and weddings have always been a favorite of his.  Take a look at his wedding photography portfolio and have him shoot your Maui wedding!



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