For some reason I always seem to miss the best events on vacation. I either forget to check the local calendar or I’m not there during the weekend of the gourmet food fair and film festival. It’s too bad because it’s hard to plan my trip around smaller events that only happen once in a blue moon.
Luckily, I’ve found a solution! Rather than plan around the major calendar events, I’ve found the best monthly, weekly, and even daily Maui events. I’ve gone through plenty of local websites and individual blog posts to find the best Maui events that are fun for all ages.
Maui's Art Scene
1. Lahaina Art Night – Did you know that Lahaina has more art galleries per capita than any other town in America? And they’re all along the happening Front Street, which is packed with shops, restaurants, and bars. Every Friday from 6 – 10 pm, the galleries host a free “Art Walk” with featured artists and refreshments. Be sure to pick up the gallery map and guide at the Lahaina Visitors Center, open from 9 am – 5 pm.
Better yet, if you’re in Maui on the second Friday of the month they kick the festivities up a notch. The town closes off Front Street for a fair with dozens of vendors, live music, and performers. For the best free parking, many people recommend parking near Hilo Hatties or the lot by Maui Medical Group.
2. Art under the Banyan Tree – I can’t think of a better place to cool off than in the shade of Maui’s famous Banyan Tree. And if you come on the weekend you can catch the local arts and crafts festival. This specific Maui event is great because you get to see the work of local Maui artists and if you have young kids they won’t get bored. It’s very interactive with free face painting and kid-focused art projects. Meanwhile you’ll discover everything from paintings and wood carvings to jewelry, glass work, ceramics, and photography.
The event runs from 9 am – 5 pm, two Saturdays a month. You can find the calendar for this event at the Lahaina Arts Society.
Live Music on Maui
There are a few restaurants in Lahaina where you can dine to live music almost every day. Head over to Front Street for music at Kimo’s, Cheeseburger in Paradise, and Lahaina Fish Company, or Ka'anapali Beach for music at Hula Grill and Leilani’s on the Beach .
Evenings and nights check out Longhi’s for a steak dinner over jazz and salsa music or come for rock on Fridays. If you like late-night jazz, Java Jazz is open until 2 am and features a full bar and local musicians.
3. Slack Key Guitar Series – Other than the 'ukulele, Hawaiian folk music is epitomized by the slack key guitar. It has a distinct sound, kind of like a softer version of the banjo that drifts more than stings, and flows in sync with the laid back melodies of Hawaiian singing.
If you want to hear it live, I’d highly recommend the Slack Key Guitar Series hosted every Wednesday and Thursday evening by the Napili Kai Beach Resort. I must warn you, this isn’t your typical Luau music. Be prepared for some authenticity. This Maui event is MC’d by local artists George Kahumoku and Da Ukulele Boyz. Check them out! Doors open at 6:45 pm and the show starts at 7:30.
Tickets are $45 at the door, but if you buy online you can get them for $37.99. They also offer a dinner show for extra at the Sea House Restaurant at Napili Kai Beach Resort. Listen to the masters first to see if this is your jam.
4. Hawaiian Music Series in Lahaina – If you happen to be in downtown Lahaina on the last Thursday of the month, head over to the corner of Dickenson & Front Streets from 6 - 7:30 pm. The Baldwin Home Museum hosts a FREE concert with local musicians. Even though chair seating is limited you can lounge on the law or the stone wall that runs along the property.
Farmers Markets & Local Crafts
I love going to the farmers market back at home, but I’ve actually never been to one on vacation. I couldn’t think of a better place to sample local produce than Maui. With so many different climates and native tropical fruits, I’d expect a farmers market to be one of the best ways to get a taste of the island.
Fortunately, there are two great farmers markets close to the major resorts.
5. Farmers Market of Maui-Honokowai:West Maui – If you plan on cooking during your vacation, the Honokowai Farmers Market is one of the best farmers markets to go to. It’s right next door to the first market where you can pick up fresh caught ono and mahi-mahi to go along with local kula greens and local avocados. Also, the bagels here are “unreal.” Even if you’re a purist, you have to try the pineapple bagel with passion fruit cream cheese. They also come in coconut and a handful of unusual flavors that you’ve probably never thought could taste good in a bagel. The market runs Monday, Wednesday, and Friday from 7 - 11 am.
On the weekend check out the Launiupoko Farmers Market , which runs Saturdays, 8 am - 12 pm.
6. Farmers Market of Maui-Kihei: South Maui – It’s very hard to beat the freshness, quality, and even prices of the produce at the Kihei Farmers Market . You can get pineapple, coconut, Maui apple bananas (mini-bananas), starfruit, maui onions, kula cucumbers, and papaya all grown organically by local farmers. Keep an eye out for the Sharwil avocado, which is considered to be the world’s best avocado and due to USDA restrictions, can only be found in Hawaii.
There’s also quite the selection of jams, juices and fresh baked goods that are better, more authentic and actually cheaper than the major grocery stores. Since the market shares a parking lot with the ABC store, you can always to do a quick spot check to compare pricing. This farmers market is a weekly Maui event that runs Monday through Friday, 8 am - 4 pm.
On the weekend you can checkout the Lipoa Street Farmers Market , which runs Saturdays, 8:30 am - 12 pm.
7. Rare Local Crafts at the Swap Meet – This is where you find rare handmade crafts, jewelry, and souvenirs, before they make it into the locked glass cabinets of boutique shops. It only costs $.50 a person to get into this flea market – which runs every Saturday from 7 am - 1 pm – and is filled with local artisans, vendors, and jewelers. If you’re looking for jewelry, I’ve heard a few people recommend Tim Hackbarth who specializes in freshwater pearls, earrings, and necklaces. Indies Attic puts an interesting spin on jewelry by crafting everything from recycled materials. You can also find handmade soaps, candles, wind chimes, sarongs, and of course Tikis. This is a great place to get gifts for everyone back home, and since it’s right next to the airport you can pick up something quickly and even grab lunch to go at one of the food stands.
Street Fairs & Festivals
No matter when you’re on Maui, there’s a distinct street fair to visit. Every Friday, a different town hosts a celebration where the streets are closed off and flooded with food carts, local vendors, and live music. This Maui event is not to be missed. Here’s a quick list of these traveling festivals.
8. First Fridays in Wailuku – Wailuku is the seat of Maui government and its financial capital, but it still knows how to throw a party. Check out the beer garden for cold local Maui brews to go along with a “rainbow of local cuisine.” Among the craft vendors you can sometimes find strolling magicians putting on a show as they go. If you have time, head over to the exhibits at the nearby Maui Historical Society.
Runs first Friday of the month, 6 - 9 pm.
9. Second Fridays in Lahaina – Lahaina blends the best of Maui art and nightlife in one place. So when Maui’s Friday festival comes to town you know it’s going to be a good time. The Front Street art galleries light up until 10 pm and the whole drag is filled with music and delicious food. Often performers from 'Ulalena, a Cirque de Soleil style event will be out singing and meeting fans.
Runs second Friday of the month, 5 - 8 pm.
10. Third Fridays in Makawao – Makawao is Maui’s cowboy town. This upcountry hamlet is set in the Maui highlands between Mt. Haleakala and the ocean. Their party features classical Hawaiian music, farm fresh food, dancing, and even a fire show. If you decide on exploring Maui’s upcountry one day, the Makawao street party would make a great finale.
Runs third Friday of the month, 6 – 9 pm.
11. Fourth Fridays in Kihei – Beyond great food and live music, Fourth Friday in Kihei has a Keiki/Youth Zone with family-friendly activities and arts and crafts. Many of the shops in this South Maui beach town set up booths where they offer discounts on souvenirs.
Runs fourth Friday of the month, 6 – 9 pm.
12. 'Ulalena – 'Ulalena is a powerful retelling of Hawaiian history and mythology through interpretive dance, music, and acrobatics. Believe it or not, Cirque de Soleil actually wrote the production, so it has a similar “wow” factor. If you’re looking for a beautiful evening performance in Lahaina, then 'Ulalena is a must see. The Maui Theatre, which puts on the show, is in downtown Lahaina, an easy walk from all the Front Street restaurants.
Tickets are a bit expensive, but you can find a discount here at hawaiidiscount.com. If this isn’t available, Yelp also offers a discount.
When: Monday, Tuesday, Thursday, Friday, 5 – 6:30 pm with check-in at 4:30 pm.
13. Kupanaha: Magic Dinner Theater – Kupanaha is one of those events that kids will absolutely love. But there’s enough humor and awe mixed in to keep adults entertained. For over a decade, this family-run show has combined magic, illusions, hula, and comedy. The dinner show takes place in a Copacabana-style lounge at the Kupanaha Resort, and features a three-course meal with drinks included in the price. Find tickets here.
When: Tuesday through Saturday, 4:30 pm – 7:30 pm.
14. Old Lahaina Luau – Set in an intimate venue in front of the ocean in Lahaina, the Old Lahaina Luau is never over crowded. You’ll find some of the best Luau food in Maui with delicious kalua pork wrapped in banana leaves and pineapple-marinated chicken. The staff here has the Luau experience down to a science, offering great service throughout the show. You’re served a mai tai as soon you walk in, and then treated to an open bar.
As Luau’s go, this Maui event is very traditional with a strong attention to the dance and musical performances. Don’t expect a Polynesian fire show or Samoan knife dancing, since these acts aren’t native to Hawaii.
It’s a good idea to book in advance, since the show can sell out quickly and the tickets are cheaper online. This Luau is great for all ages, but there tends to be more adults than kids. To find your perfect Luau check out our Maui Luau guide.
When: Every Night April 1 – September 30, 5:45 pm – 8:45 pm
Every Night October 1 – March 31, 5:15 pm – 8:15 pm.
15. Cliff Diving Ceremony – Every night at sunset, a man playing a Hawaiian warrior lights the tiki torches along Ka’anapali Beach as he runs out to the Cliffs of Black Rock (Pu'u Keka'a), Maui’s western most point. After offering a high lei to the heavens, he chucks his torch into the water and dives 30 feet into the ocean below. The tradition commemorates King Kahekili of Maui who performed the same ritual over 200 years ago.
The cliff diving ceremony is short and sweet. Best of all it’s free! Since it’s near Whalers Village there’s plenty of great dining options just a short walk along the beach. I’d recommend the Hula Grill or Leilani’s on the Beach for a casual meal or Roy’s – Ka'anapali for something a little fancier.
Photo: Maui Sunset Resort