Friday, September 25

Morgan Jay: Goofy Guy Tour
Comedian and musician Morgan Jay brings his Goofy Guy Tour to the Maui Arts & Cultural Center’s Castle Theater from 7:00 to 9:00 PM. Known for blending acoustic music, Auto-Tune, and audience interaction into his comedy, Jay has built a major following online and on tour.

Whalers Village Movie Night
Bring the family to a complimentary outdoor movie night at Whalers Village’s ʻOhana Courtyard. Transformers One is scheduled to screen Friday evening, beginning 30 minutes after sunset.

Free Range Comedy
Enjoy an evening of live improv with Free Range Comedy at ProArts Playhouse in Kihei. The show begins at 7:30 PM, with seating starting at 7:00 PM.

Live Music at Duke’s Beach House
Enjoy lunch and live music from Kaleo Philips at Duke’s Beach House in Lahaina from 12:30 to 2:30 PM.

Saturday, September 26

Paniolo Night
Maui Preparatory Academy hosts its annual Paniolo Night in Lahaina from 5:00 to 9:00 PM. This community celebration of Hawaiian cowboy culture includes family-friendly activities and entertainment.

Yoga with the Pups
Start the morning with an outdoor yoga class at Maui Humane Society’s Cruise’s Yard from 10:00 to 11:00 AM. Registration is $40, with proceeds benefiting the shelter animals.

Upcountry Farmers Market
Shop local produce, prepared foods, and artisan goods at the Upcountry Farmers Market at Kulamalu Town Center in Pukalani. The weekly Saturday market runs from 7:00 to 11:00 AM.

Whalers Village Movie Night
Whalers Village continues its complimentary outdoor movie series in the ʻOhana Courtyard with Minions: The Rise of Gru, beginning 30 minutes after sunset.

Sunday, September 27

8th Annual Oktoberfest at Maui Brewing Co. Kihei
Maui Brewing Co. hosts its 8th Annual Oktoberfest celebration from 5:00 to 8:00 PM. The all-ages event features live music, festive games, Oktoberfest-inspired food, beer, and limited-edition steins. Admission is free.

Maui Sunday Market
Spend Sunday afternoon at the Maui Sunday Market in the Kahului Shopping Center parking lot from 4:00 to 8:00 PM. The free community market features food trucks, local vendors, products from Maui small businesses, and live entertainment.

Long Beach Dub Allstars
Long Beach Dub Allstars perform at da Playground Maui in Māʻalaea at 7:00 PM. Expect a high-energy mix of reggae, ska, punk, and rock.

Weekend Highlights: August 7–9

• Kapalua Wine & Chef Series — August 8: Enjoy an elevated multi-course dining experience at The Ritz-Carlton Maui, Kapalua, featuring PlumpJack wine pairings and a special appearance by Chef Kristen Kish.
• Bonnie X Clyde — August 8: Head to da Playground Maui in Wailuku for an energetic electronic dance music performance.
• Jewelry Making & Family Activities — August 8: Bring the keiki to Pizza Madness Maui in Kihei for hands-on crafts, jewelry making, and family-friendly fun.
• Paniolo Nights — August 9: Experience a country-inspired evening at Ocean Vodka Organic Farm and Distillery in Kula, complete with live music, local food, and upcountry atmosphere.

Weekday Picks: August 10–13

• Mele: The Hawaiian Music Experience — August 11: Step into an immersive 360-degree presentation celebrating traditional Hawaiian music and visuals at Maui Ocean Center.
• Kuraya Magic Show — August 11: Magician David Kuraya brings close-up sleight-of-hand and theatrical magic to Royal Lahaina Resort & Bungalows.
• Aurum Maui Supper Club — August 12: Settle in for an intimate five-course chef’s table experience with Chef Taylor Ponte at Aurum Maui in Wailea.
• John Cruz Island Style Series — August 12: Award-winning local artist John Cruz performs an intimate live set at ProArts in Kihei.
• Ken Emerson, Kevin Brown & Wainani — August 12: Enjoy an evening of Hawaiian slack-key guitar and island music at the Slack Key Show in Lahaina.
• Artisan Market Day — August 13: Browse locally made goods, artisan products, and skincare offerings during the weekly outdoor market at South Maui Gardens in Kihei.
• Film Screening: Māʻalaea’s Taste for Regeneration — August 13: Join a free community documentary screening and post-film Q&A at Maui Ocean Center.
• DUETS: Sheryl Renee Salutes — August 13: Catch a cabaret-style tribute performance at ProArts Playhouse in Kihei.
• The Mulligan’s Magic Show — August 13: Enjoy an interactive, family-friendly evening of tableside and stage magic at Mulligan’s on the Blue in Kihei.

Ali Wong Live – Second Show Added
July 31, 2026 | 7:00 PM
Maui Arts & Cultural Center – Castle Theater, Kahului

Due to overwhelming demand, Ali Wong has added a second show on Maui. Expect sharp, unfiltered comedy from one of the biggest names in stand-up today. If you missed tickets the first time around, this is your shot.

Hot Country Night Kūpuna Prom
July 31, 2026 | 5:30 PM
Helene Hall, Hāna

A unique, community-driven country night with an island twist. Enjoy live country music, local food, and a welcoming dance floor—all supporting Hale Hulu Mamo. A great mix of fun and purpose.

South Shore Tiki Lounge – Live Music & Late Night DJs
August 1, 2026 | Live Music 4:00–6:00 PM | DJs from 9:30 PM
Kihei

Start with live acoustic vibes from Eammon McKinney, then transition into a high-energy nightlife scene with DJs spinning late into the evening. One of South Maui’s most consistent nightlife spots.

Island Soul Band Night
August 2, 2026 | 5:30–8:30 PM
Mulligans on the Blue, Wailea

A lively weekly dance party featuring soul, funk, and classic rock. Great sunset views, strong crowd energy, and a reliable spot if you want live music without the big venue feel.

Sunset Sessions at Alaloa Lounge (Ritz-Carlton Kapalua)
Nightly | 6:00–9:00 PM
Kapalua

For a more laid-back evening, Alaloa Lounge offers sunset cocktails paired with live acoustic sets—think slack-key guitar, Hawaiian vocals, and rotating local talent in a high-end setting.

Queen Kaʻahumanu Center Farmers Market
July 31, August 4 & 5 (Morning Hours)
Kahului

A staple for local produce, fresh fruit, and small vendors. Ideal for a casual morning stop or picking up local goods.

Cats & Crochet – Cat Café Maui
Weekly Evening Event
Kahului

A relaxed social event combining crafting and community with adoptable rescue cats. A low-key option if you’re looking to slow things down.