Kula Country Farms Pumpkin Patch

Kula Country Farms, Kula — Oct 1–31, 9:00 am–4:00 pm (last entry 3:45 pm)

Set on the slopes of Haleakala, this all-October patch is an easy Upcountry outing with rows of carving and pie pumpkins (from giant to mini), specialty gourds and squashes, bright sunflowers, and plenty of photo spots. Admission is $5 (keiki 3 & under free) and includes access to the keiki garden and farm stand, which stocks produce, flowers, “succulent pumpkins,” carving tools, and seasonal treats. Expect drinks and snacks on weekdays, hot food on weekends, limited picnic tables, and weekend parking in the pasture just past the stand on Kula Hwy—so wear closed-toe shoes and consider bringing a small cart for your haul.

$5 entry (keiki 3 & under free); on-site parking; photo spots and sunflower patch. Tickets/info via farm site.

Maui County Fair (98th Annual)

War Memorial Special Events Complex, Wailuku — Oct 2–5 (Thu 4:30–11:00 pm; Fri 4:30 pm–midnight; Sat 9:30 am–midnight; Sun 9:30 am–11:00 pm; parade Thu 4:30 pm)

Maui’s hometown fair returns with four days of live entertainment, ono grinds, classic E.K. Fernandez rides, and community exhibits—from livestock and poultry to fiber arts and student art—spread across the War Memorial grounds. Opening night starts with the parade through Kahului before the midway lights up; weekend hours expand for daytime fun, and ride specials run on Saturday and Sunday. Look for a new 2025 coaster (“Wacky Worm”) plus an inclusive Special Fair Day on Friday morning designed to make the experience easy and accessible.

Parking fills quickly near War Memorial; check same-day updates on the fair site or County alerts. Admission and presale locations posted online.

Brad Williams: The Growth Spurt Tour

Castle Theater, Maui Arts & Cultural Center (Kahului) — Wed, Oct 8, 7:30 pm

High-energy, quick-witted, and relentlessly crowd-pleasing, Brad Williams brings a powerhouse stand-up set to Maui. A touring headliner since his teens, Williams has sold out theaters around the world and stacked a résumé of late-night spots and acclaimed specials—including Fun Size (a breakout hit on Showtime), Daddy Issues, and Netflix’s The Degenerates. He also notched a Las Vegas milestone as the first stand-up to headline a Cirque du Soleil production (Mad Apple at New York-New York), earning rave reviews for his onstage command and razor-sharp timing. Beyond the stage, Williams co-created the hit podcast About Last Night with Adam Ray and appears regularly across national radio and podcast platforms. Expect rapid-fire storytelling, playful crowd work, and 100% live-wire momentum from start to finish.

Reserved seating; online sales via MACC; mature subject matter noted.

Maui Jazz & Blues Festival Series: Sax & More w/ Hawaii Jazz

ProArts Playhouse, Kihei — Thu, Oct 9, 7:30–9:00 pm

An intimate, musician-forward concert led by Dr. Joie Yasha Taylor (sax, flute, vocals) with Jeff Hellmer (piano), Ashton Yarbrough (bass), and Indio (drums), serving up Latin, swing, and straight-ahead jazz in a 90-minute, no-intermission set.

Assigned seating; compact venue with excellent acoustics; tickets on the ProArts site.

Kolohe Kai — What Aloha Means

A&B Amphitheater, Maui Arts & Cultural Center (Kahului) — Fri, Oct 10, 6:00 pm (gates 5:00 pm)

Kolohe Kai brings a decade-plus of island-pop energy led by singer-songwriter Roman De Peralta of Oahu. Known for blending ukulele-driven local vibes with roots reggae and a polished pop/R&B sheen, the project has notched 10 Island Reggae hits since Roman signed at 17. Early releases—shaped by island elders and mainland influences like Rebelution—set the tone on the debut This Is The Life, while recent collaborations with Grammy-winning producer Brian Kierulf on “Catching Lightning” and “Heartstrings” showcase a more expansive, radio-ready sound. The accolades back it up: Kolohe Kai has been one of Hawaii’s most-streamed reggae acts of the past decade (40M+ streams in 2020), with Paradise earning Na Hoku Hanohano’s Reggae Album of the Year and Summer To Winter taking Reggae Album of the Year at the Island Music Awards.

GA standing; VIP/meet-and-greet options; no outside food/drink; ticketing via MACC.

The Rocky Horror Show (Opening Weekend)

Historic Iao Theater, Wailuku — Fri, Oct 17, 7:30 pm; Sat, Oct 18, 7:30 pm; Sun, Oct 19, 3:00 pm (continues Oct 24–26 & Oct 31–Nov 2)

Do the Time Warp at Maui OnStage’s cult-classic rock musical, where sweethearts Brad and Janet stumble into Dr. Frank N Furter’s outrageous world—complete with optional audience participation and theater-approved prop bags sold on site (outside props not allowed). The listing outlines content advisories (mature themes/language) and special effects (fog, haze, strobes), plus venue policies: all bags are searched, small bags only, no outside food/drink or water bottles, and late arrivals may be seated at intermission.

Doors ~45 minutes before; Fri/Sat 7:30 pm, Sun 3:00 pm; content/effects advisories on the listing.

First Hawaiian Bank presents the 27th Annual Roy Yamaguchi Golf Classic

Kaanapali Golf Course & Roy’s Kaanapali — Fri, Oct 24 (registration 10:00 am; shotgun 11:30 am; awards reception & dinner to follow)

Swing into a day of good fun and good deeds at Kaanapali Golf Course. This beloved play-and-dine tournament brings together golfers, community leaders, and acclaimed chefs Roy Yamaguchi and Alan Wong for a memorable 18-hole round dotted with chef stations serving fresh, local flavors. Between swings, enjoy thoughtfully paired cocktails and ice-cold brews, then cap the day at the 19th-Hole Awards Dinner hosted at Roy’s Kaanapali. Proceeds benefit Imua, a local nonprofit.

Recent updates show limited availability/sell-outs—check HFWF channels for status.

TUMUA: The Chee Hoo Tour

Castle Theater, Maui Arts & Cultural Center (Kahului) — Fri, Oct 24, 7:30 pm & Sat, Oct 25, 7:30 pm

Born and raised on Oahu, Tumua is a stand-up comedian, podcaster, former collegiate athlete, actor, and social media phenom with a following in the hundreds of thousands across Instagram, TikTok, Facebook, and YouTube. Expect high-energy, Hawaii-style storytelling, sharp crowd work, and new material drawn from his wildly popular online sketches and recent YouTube specials—Strictly Aloha and Talk Story: The Crowd Work Special. He has sold out clubs, theaters, and even arenas nationwide, and appears in Disney’s 2025 live-action Lilo & Stitch.

Two show dates; online ticketing via MACC; upgrade package available.

Hawaii Food & Wine Festival — World of Wagyu, Wine & Whiskey

Sheraton Maui Resort & Spa, Kaanapali — Sat, Oct 25, 6:00–9:00 pm

An oceanside grand tasting where luxury meets bold flavor: savor ten chef-crafted dishes featuring Wagyu from Japan (including A5), the U.S., and New Zealand, alongside a curated pour list from master sommeliers, winemakers, and top mixologists serving whiskey-forward cocktails.

Outdoor, resort-casual evening; check HFWF for ticket releases or charitable options if sold out.

Fins & Frights (Halloween at the Aquarium)

Maui Ocean Center, Maalaea — Sat, Oct 25, 6:00–9:00 pm

Celebrate Halloween early at the Aquarium of Hawaii with costume contests, trick-or-treat stations, arts & crafts, diver presentations, and a 3D program in the Sphere Theater—easy parking and an all-ages vibe make this a stress-free night out.

Family-friendly; admission/membership details and updates on the MOC events hub.