Maui Events October 2019

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Aloha and hello, travelers. Hats off to you, because you’re on Maui during one of the best months of the year! Not only can you attend the famous Front Street Halloween Celebration in Lahaina, but there are plenty of other opportunities for fun, from the annual Maui Fair to epic concerts and more.

For more information or to see the best weekly, monthly and yearly celebrations, check out our calendar of Upcoming Maui Events

maui no ka oi

 

Maui Events October 2019

Saturday Evenings (October 5th, 12th, 19th & 26th):

Maui Chef’s Table – Come experience the Maui Chef’s Table culinary adventure on the grounds of Maui Tropical Plantation! Enjoy multiple courses of unique, farm-fresh cuisine and craft cocktails, all prepared in a gorgeous island setting.

maui fairs and festivals

October 1st

Kula Country Farms Pumpkin Patch Opening: Find your perfect pumpkin at this beautiful Upcountry location, open daily until October 31st from 9 am to 4 pm.

October 2nd

Jazz at the Shops of Wailea: Free jazz concert with music by Kelly Covington at the Shops of Wailea. Concert begins at 5:30 pm in the Upper-Level shopping area.

October 3rd

97th Annual Maui Fair Opening Parade: Opening day of the 97th annual Maui Fair kicks off with the traditional parade. The parade runs from the UH Maui campus to the War Memorial Fairgrounds, beginning at 4:30 pm. The fair is open until 11 pm.

October 4th

Wailuku First Friday: Live music, ono grinds, shopping and family fun entertainment on Wailuku’s historic Market Street.

97th Annual Maui Fair: Maui’s biggest event returns for its 97th year. Bring the entire family along for a weekend full of fun and discover the meaning behind this year’s appropriately named theme, ‘Make Memories, Share Moments’. With a slew of traditional carnival rides, deliciously diverse food, some of the island’s best entertainment, and a handful of exhibits and games, there is something for everyone at the Maui Fair.

October 5th

One Little Finger – Concert and Film by Rupam Sarmah: Maui premiere of the award-winning film “One Little Finger”, a story of an American neurologist who uproots her life to work with children and adults with disabilities in India using music therapy. The show opens with a concert by Rupam Sarmah and special guests George Kahumoku Jr. and Rock Hendricks. The show starts at 7 pm in the McCoy Studio Theather, Maui Arts and Cultural Center.

97th Annual Maui Fair: Maui’s biggest event returns for its 97th year. Bring the entire family along for a weekend full of fun and discover the meaning behind this year’s appropriately named theme, ‘Make Memories, Share Moments’. With a slew of traditional carnival rides, deliciously diverse food, some of the island’s best entertainment, and a handful of exhibits and games, there is something for everyone at the Maui Fair. Open until midnight.

Family Class at Island Art Party: Get the family together for an afternoon of fun and creativity at Island Art Party’s Family Class. Learn how to paint a panda and take home your own artwork.  Ages 8 and up are welcome, class runs 2:00 pm to 4:30 pm. Reservations are recommended.

October 6th

Richard Thompson Electric Trio: With over 40 albums, several Grammy nominations, and named as one of Rolling Stone’s Top 20 Guitarists of All Time, Richard Thompson is undoubtedly one of the world’s greatest electric and acoustic guitar masters. Catch this guitar legend at the Maui Arts and Cultural Center’s Castle Theather, show begins at 7:30 pm.

Garden Party 2019: Spend an afternoon feasting on dishes from Maui’s top restaurants, sampling wine, and enjoying live entertainment from the island’s best performers at the Youkuchi Family Estate in Wailuku. Proceeds go towards Maui Academy of Performing Art’s scholarship fund, which aims to provide any child on Maui the opportunity to take dance or drama classes.

97th Annual Maui Fair: Maui’s biggest event returns for its 97th year. Bring the entire family along for a weekend full of fun and discover the meaning behind this year’s appropriately named theme, ‘Make Memories, Share Moments’. With a slew of traditional carnival rides, deliciously diverse food, some of the island’s best entertainment, and a handful of exhibits and games, there is something for everyone at the Maui Fair. Open until midnight.

maui travel blog

October 8th

An Evening With Nainoa Thompson: Maui Nui Marine Resource Council presents ‘An Evening With Nainoa Thompson: In A Changing World, Hope Comes With Action’ at the historic Iao Theather. Nainoa is a master navigator who led the famous Hokulea on the “Malama Honua” global voyage. With numerous community awards from organizations such as NOAA and even the Dalai Lama, Nainoa will unearth the true meaning of the Hawaiian principle of “malama” (to caretake). The show begins at 6:00 pm and tickets run from $10 to $20.

October 10th

Christain Sands Trio: Join the Christain Sands Trio for a night of groovy jazz at the Maui Arts and Cultural Center. Young pianist Christain Sands along with drummer John Davis and bassist Yasushi Nakamura form the dramatic Christian Sands Trio, who aim to entertain, engage, and tell stories through their soulful sounds. The show begins at 7:30 pm in the Castle Theather.

Dean Martin – Classic Songs With John Wilt: Crooner John Wilt performs hit songs by American icon Dean Martin in this one man show at the Maui Arts and Cultural Center’s McCoy Studio Theather. All proceeds will go to benefit Maui Academy of Performing Arts (MAPA).

October 11th

Artist 2 Artist: Henry Kapono and Jerry Santos: Jam and talk story with two of Hawaii’s most renowned musicians, Henry Kapono and Jerry Santos in this intimate concert series at the Maui Arts and Cultural Center. Here the artists offer a personal experience with the audience by telling stories, answering questions, and jamming together, of course!

Lahaina Second Friday Town Party: Take to the street, Front Street, that is, for the Lahaina Second Friday Town Party. Enjoy live music, browse through Lahaina’s art galleries, and find deals on locally made goods and grinds.

October 12th

Family Class at Island Art Party: Get the family together for an afternoon of fun and creativity at Island Art Party’s Family Class. Paint a sunset scene on a unique wooden turtle and take home your own artwork! Ages 8 and up are welcome, class runs 2:00 pm to 4:30 pm. Reservations are recommended.

R. Carlos Nakai Quartet: Of Navajo-Ute heritage, R. Carlos Nakai is one of the world’s greatest masters of the Native American flute. His quartet, complete with trumpet, vocals, and drums provides a soulful, rhythmic, yet meditative blend of sound which is undoubtedly danceable. Join the R. Carlos Nakai Quartet at the Maui Arts and Cultural Center’s McCoy Studio Theather, show begins at 7:30 pm.

MAMo Wearable Art Show: Celebrate Hawaiian art, fashion, and design with the PA’I Foundation’s unique wearable art show. The MAMo Show highlights all types of Native Hawaiian artists, from traditional designers, contemporary designers, tattoo artists, and traditional cultural practitioners.

October 13th

Maui Marathon and Half Marathon: The Maui Marathon holds the title of several superlatives: the oldest marathon west of the Mississippi, one of the most scenic marathons in the nation, and the longest consecutively held running event in the state of Hawaii. With five races (marathon, half marathon, relay marathon, 10k, and 5k) spanning from Kahului to Ka’anapali, the Maui Marathon is also a Boston Marathon qualifying event.

The Merwin Conservancy Presents Pualani Kanahele in the Green Room: Spend an evening with Hawaiian scholar, kumu hula, writer, educator, musician, and dedicated community leader Dr. Pualani Kanahele. Join Kanahele and the conservancy’s founder, W.S. Merwin, as they discuss and dissect Merwin’s epic Hawaiian poem, ‘The Folding Cliffs’.

October 16th

Concert at the Shops: Free concert at the Shops of Wailea featuring the Hawaiian folk duo Kupaoa and Halau. The show begins at 5:30 pm at the lower level fountain courtyard.

Artist Talks: Art and Activism: Join artists Kanani Miyamoto and Paul Mullowney for a walkthrough and discussion of the Maui Art and Cultural Center’s current exhibit, Art and Activism. The walkthrough is followed by a demonstration at the UH Maui College campus.

October 17th

Artist Talks: Art and Activism: Join artists Kanani Miyamoto and Paul Mullowney for a walkthrough and discussion of the Maui Art and Cultural Center’s current exhibit, Art and Activism.

October 18th

Starry Night Cinema: Enjoy a night under the stars with the whole family for a free screening of ‘Aladdin’ at the Maui Arts and Cultural Center. Bring a blanket or a beach chair and snag a space on the lawn. Food and drinks from local food trucks available for purchase. Gates open at 5:00 pm.

October 19th

North Shore Noodle Ride: Maui Bicycling League presents the first “North Shore Noodle Ride”, a 12-mile roundtrip ride along Maui’s north shore from Kahului to Paia and back. Participants will be provided with a pool noodle to attach to the left side of their bike that reads ‘3-foot law’ in order to raise awareness surrounding Hawaii’s new Safe Passing Law. The Safe Passing Law requires drivers to allow three feet of separation when passing cyclists. Visitors and residents alike are welcome to join.

Kris Kristofferson and The Strangers: Country music star Kris Kristofferson is coming to the Maui Arts and Cultural Center, accompanied by one of country music’s favorite bands, The Strangers. Now 83, Kris Kristofferson’s achievements include three Grammy awards, 30 albums, and a recent role in the film ‘A Star Is Born’. Don’t miss this country music legend live at the Castle Theather.

Hawaii Food and Wine Festival: Join the Hawaii Food and Wine Festival at the Sheraton Resort for ‘Wicked Cocktails, Wicked Plates’, a night of food, drinks, fireworks, and fun under the stars. Sample dishes from 13 different chefs and craft cocktails from Hawaii’s best mixologists before wrapping up the night with a fireworks show.

Family Class at Island Art Party: Get the family together for an afternoon of fun and creativity at Island Art Party’s Family Class. Learn how to paint a unicorn and take home your own artwork!  Ages 8 and up are welcome, class runs 2:00 pm to 4:30 pm. Reservations are recommended.

maui events 2018

October 20th

Trio con Brio Copenhagen: Experience the musical stylings of what is known as one of the best piano trios in the world, Trio con Brio Copenhagen. Composed of Korean-born sisters, Soo-Kyung Hong (cello) and Soo-Jin Hong (violin), along with Danish pianist, Jens Elvekjaer, Trio con Brio Copenhagen plays a critical role in the Scandinavian contemporary music scene. The trio has also won many major competitions around the world and is featured regularly at some of the world’s most premier venues.

Hawaii Food and Wine Festival: Get a taste of Italy from the Hyatt Maui with Hawaii Food and Wine Festival’s “Pasta la Vista” event. Enjoy a six-course meal prepared by several master Italian chefs who add a modern flair to some of the most traditional and beloved Italian dishes.

Keiki in the Kitchen: Round up the keiki for an afternoon of fun at Whaler’s Village. Dress up in your Halloween costume and decorate cupcakes with “Ace of Cakes” star Duff Goldman, trick or treat on “Treat Street”, plant succulents, learn how to coconut weave, and even get autographs from over 10 celebrity chefs!

October 25th

Okaidja Afroso: Okaidja Afroso is a singer, guitarist, percussionist, and dancer hailing from the village of Kokrobite on the west coast of Ghana. With four albums, Okaidja Afroso has formed a deep connection to the music of the African Diaspora and has paved the way for a new medium of music that has become completely his own. Self-taught on guitar, Okaidja Afroso’s sound produces something pure and ultimately unique.

Kihei Fourth Friday Town Party: Gather at Azeka Center (mauka side) for the Kihei Fourth Friday Town Party. Enjoy free entertainment, arts and crafts for the keiki, and a handful of delicious food from some of Maui’s best food trucks.

October 26th

Ridge to Reef Rendevous: Learn about ocean conservation efforts and what it means to “malama Maui” at the 10th annual Ridge to Reef Rendevous at Kahekili Beach in Ka’anapali. The free event kicks off with a keiki catch and release fishing tournament, followed by a scavenger hunt, tours of the “haunted reef”, interactive displays, and lunch provided by Westin Nanea Ocean Villas and CJ’s Deli & Diner.

maui events october 2018

October 27th

XTERRA World Championship: Maui was the birthplace of the offroad triathlon. Now in its 24th year, the XTERRA World Championship returns for a 1 mile swim along D.T. Flemings Beach Park, a 20 mile, 3,500 ft elevation gain bike ride, and a 6.5-mile trail run. Watch the action unfold from the XTERRA Spectator Village, where you can indulge in food, drinks, games, and music, along with kid-friendly activities like bounce houses and face painting.

October 31st – HAPPY HALLOWEEN!

Lahaina Front Street Halloween Party: Each year, Lahaina Town is the host of one of the largest Halloween parties in Hawaii, often dubbed the “Mardi Gras of the Pacific”. Front Street closes off all streets to traffic, allowing costumed visitors and residents the chance to walk freely down the street and enjoy the many events held throughout the evening.

maui halloween celebration 2018

 

Mahalo for checking out the top activities on Maui in October! Remember to celebrate responsibly on Halloween, and we look forward to sharing some of our favorite photos from events around the island.

3 Comments

  • Hi Kelsey! I’ve been reading your articles about Maui and they are excellent! I had some questions that I hoped you’d be able to answer and I don’t know where to turn for the answers.

    My girlfriend and I have done a nomadic style of living. Traveling across the 48 and working here there and yonder. We lived in a camper in random spots for a long time. Now we are living in our vehicles. We still hold down jobs and have everything we need. We wanted to continue to do this, except in Hawaii, Maui specifically. I’ve read a lot about how it’s illegal to sleep in cars, whereas here, no one really cares. Is it possible to be able to move to Maui and continue to live this nomadic lifestyle? Where we can find jobs to pay our vehicle payments, but avoid paying rent or having to settle down in any one location? We want to explore all over the place and work enough to get by as we have been doing, while having the time to still go anywhere! Is that possible, or would going there be a mistake that results in nothing but citations and pretty much being forced off the island and back to the 48? I’d love to hear your thoughts on car living in Maui and the possibility of it! I’d be happy to talk through the forum here, or if you had time, it’d be more convenient to email back and forth. Would love if you could educate me a little. We’ve been gearing up to move over there and are getting close to being able to, we just want to know it won’t be a mistake and that our lifestyle is possible over there! Thank you so much for your time Kelsey!

  • Hello, We will be joining the festivities on front street Halloween , my wife is dressing as Gwen Staffani from no-doubt , would I be able to reach out to the house band to preform “spiderwebs”off the tragic kingdom cd?
    She looks and sings very close to Gwen.
    Thank you,
    Geoff Freeland 1716-440-8094

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