Maui Events May 2019

Maui calendar

Welcome to The Valley Isle! With 81 beaches, an vast array of climates and scenic landscapes, and more aloha than you can throw a coconut at, May is a stellar time to be on Maui. Mostly just like every other month. This month, there are plenty of thrilling local events to look forward to, from top notch dining events to festivals, concerts and much more.

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

maui top things to do 2019

 

Maui Events May 2019

Select Thursdays & Saturday Evenings (May 4th, 9th, 18th & 25th):

Maui Chef’s Table – Come experience the Maui Chef’s Table culinary adventure on the grounds of Maui Tropical Plantation! Enjoy 9 courses of unique, farm-fresh cuisine and craft cocktails, all prepared in a gorgeous island setting. Please check their calendar for dates and tickets. $150 per person, including tax and gratuity; 6pm – 9:30pm.

maui top events 2019

May 2nd

Michael Franti & Spearhead: Michael Franti is a musician, singer-songwriter, filmmaker, and humanitarian who is recognized as a pioneering force in the music industry. Come see him live at the MACC’s Castle Theater, along with opener, Jungle Man Sam.

May 3rd

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

Cazimero Lei Day Concert: Kumu Hula Robert Uluwehi Cazimero will perform in this perennially popular Lei Day event, along with the musicians and dancers from his award-winning Halau Na Kamalei – big winners at the 2015 Merrie Monarch Festival.

May 4th

Family Class at Island Art Party: From 2pm to 4:30pm, reserve a spot in Kihei’s family-friendly painting class. Painting ‘Aloha Sunset,’ this class is open for ages 8 and up.

Paddle Imua: The 8th Annual Paddle Imua follows the renowned Maliko Downwind Run from Maliko Gulch to Kahului Harbor. This one of a kind benefit race supports Imua Family Services’ Camp Imua program, a week-long recreational camp experience for school-aged children with disabilities and special needs. The public is invited to join the fun at the Hawaiian Canoe Club in Kahului for the Ohana Festival which features food trucks, booths, hula dancers, a keiki zone and the opportunity to cheer in the ocean racers as they cross the finish line.

MAPA’s Spring Extravaganza 2019: Opening the weekend on Saturday afternoon, MAPA’s annual recital features dancers of all ages strutting their stuff in hip hop, jazz, ballet, and contemporary. On Saturday evening, MAPA’s most experienced dancers present extraordinary original choreography in the MOVES dance concert, featuring guest appearances by some of Maui’s favorite dance companies.

Hawaii Champion’s Cup: See your favorite tennis legends play live in Hawaii! John McEnroe, Michael Chang, Tommy Haas, and Mark Philippoussis are all coming to Lahaina this May. These legends will square off in two one-set semi-finals with the winners battling in a championship match. It will be part of a weekend of events that kicks off Saturday, May 4 with kids clinics, VIP hit-with-the-pros sessions and a VIP party.

maui events by month 2019

May 5th

MAPA’s Spring Extravaganza 2019: On Sunday afternoon, MAPA dancers of all ages will continue strutting their stuff in hip hop, jazz, ballet, and contemporary, and Sunday evening, MAPA’s upper-level ballerinas present the magical ballet, “Cinderella.” Come join MAPA for a delightful weekend of dance!

Hawaii Champion’s Cup: See your favorite tennis legends play live in Hawaii! John McEnroe, Michael Chang, Tommy Haas, and Mark Philippoussis are all coming to Lahaina this May. These legends will square off in two one-set semi-finals with the winners battling in a championship match. It will be part of a weekend of events that kicks off Saturday, May 4 with kids clinics, VIP hit-with-the-pros sessions and a VIP party.

May 8th

Hawaii Small Business Conference: Aiming to provide many of these businesses with the rare opportunity to increase their knowledge and sharpen their professional acumen and skills, the theme of this year’s conference is “Plan, Build, Grow: Mapping A Pathway to Success.”  Hear from experts and successful business owners on employee engagement, technology in business, video marketing, data protection, success planning, tax strategies and more.

May 9th

Hawaii Small Business Conference: Aiming to provide many of these businesses with the rare opportunity to increase their knowledge and sharpen their professional acumen and skills, the theme of this year’s conference is “Plan, Build, Grow: Mapping A Pathway to Success.”  Hear from experts and successful business owners on employee engagement, technology in business, video marketing, data protection, success planning, tax strategies and more.

May 10th

Lahaina Second Friday: Live music, ono grinds, shopping and family-fun entertainment on Lahaina’s famous Front Street.

maui events calendar

May 11th

Charity Walk Maui 2019: The Charity Walk is one of the largest single-day fundraising events in Hawaii. In 2018, Maui County alone raised over $1.4 million dollars. All the funds raised went to benefit over 100 non-profit agencies! Charity Walk Maui County is run through Maui Hotel & Lodging Association (MHLA). MHLA is a nonprofit organization founded in 1987 to advocate for the Visitor Industry.

Seabury Hall 46th Annual Craft Fair: Located on the grounds of the historic Seabury Hall Campus in Makawao, the Craft Fair creates bright futures by supporting the schoolʻs scholarship programs which affect more than a quarter of our student body. Admission is $5 for adults and children 12 and under are free. Free parking is available while onsite premium parking is $10.

Artist 2 Artist with Henry Kapono – The Next Generation: Just nominated for four 2019 Na Hoku Hanohano Awards, Henry Kapono features his new hit CD, The Songs of C&K celebrating the timeless classics of legendary duo Cecilio & Kapono with a special performance of their most iconic songs in collaboration with several of Hawaii’s rising local musicians.

May 15th

Maui Waena Intermediate School Band: Join us in the Castle Theater for our annual School Band Concert Series! The concerts allow the next generation of musicians to experience the same world-class stage setting that the superstars enjoy. Free admission.

May 17th

Makawao Third Friday: Live music, ono grinds, shopping and family-fun entertainment on Makawao’s Baldwin Avenue.

May 18th

Maui Bike League’s Ride of Silence: Maui will be participating in this global Ride of Silence movement, which takes place in hundreds of locations every year to honor cyclists who have been hit or killed while riding on public roadways. Participants will ride 22 miles in silence from South Kihei’s Boss Frog’s location to Kahului and back.

11th Annual Maui Brewers Festival: The event features tasty food from local restaurants and caterers at no additional charge, beer tastings from local and national craft breweries, live music featuring Riddum Station and Flat Jackson, door prizes, a home brew competition, and lots of fun!

May 19th

HAPA – The Original: Reuniting after 17 years, the original duo of Barry Flanagan and Keli’i Kaneali’i bring back the groundbreaking sound that established the name HAPA as one of the most recognized names in Hawaiian music since their debut album hit the airwaves. See them at the MACC’s McCoy Studio Theater.

maui hawaii things to do

May 20th

Iao School Band: The public is invited to attend and support Maui’s hard-working young performing artists at this free concert at the MACC’s Castle Theater.

May 24th

Kihei Fourth Friday: Live music, ono grinds, shopping and family-fun entertainment at Kihei’s Azeka Shopping Center.

May 25th

Maui Matsuri Festival: Maui Matsuri started as a Japanese festival on Market Street in Wailuku Maui in May 1999. Today the festival transforms the grassy knolls of the UH Maui College campus into a Japanese village complete with food stalls, craft vendors, entertainment and activities for all ages.

May 29th

Andy McKee: One of the world’s finest acoustic guitarists, Andy McKee’s youthful energy and attention to song structure and melodic content elevates him above the rest. He entertains both the eye and the ear as he magically transforms the steel string guitar into full orchestra via his use of altered tunings, tapping, partial capos, percussive hits, and a signature two-handed technique.

things to do in maui hawaii 2019

Mahalo for reading our list of Maui activities in May 2019! Have an upcoming event you’d like us to include on the next post? Let us know in the comment section below or contact us directly about how to add your event to our monthly calendar and blog post. Aloha!

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