Kīhei's November Calendar and Live Music!

This week, songwriters in town for a country music festival will play three Kīhei bars for no cover charge. Their ticketed concert, the one with the $1,000 tables, is south in Wailea at the Grand Wailea. Once the festival leaves, a small nonprofit theater on the ocean side of Azeka Plaza carries most of Kīhei's evenings out through Thanksgiving weekend.

That theater is ProArts Playhouse at 1280 South Kīhei Road. It has 110 seats, and ProArts has run it at Azeka since 2009, four years after the organization started in 2005. Its November schedule has 19 events on 17 different nights and afternoons. Most of them cost less than general admission to the festival's big concert.

The festival's free hours happen in Kīhei

The No Ka ʻOi Songwriters Festival runs Nov. 5 through 7 and is back for its third year. It's presented by the Heart and Hook Foundation, and its listed beneficiaries are the Lele Aloha Foundation and the Maui Family YMCA Music Program. The festival's 2026 schedule lists the opening-day bar crawl under Nov. 5, which is today. Admission is free and you must be 21 or older. The songwriters rotate through three stops:

1. 4 p.m. at Three's Bar & Grill, 1945 S. Kīhei Road
2. 5:30 p.m. at Kahale's, 36 Keala Place
3. 7:30 p.m. at Maui Brewing Co. Kīhei, 605 Lipoa Parkway

The schedule page is the one to check before heading out. Last year's crawl had four stops and finished at South Shore Tiki Lounge and South Maui Gardens, according to Maui Now's 2025 festival preview. This year there are three stops spread across a longer evening. That leaves a 90-minute gap before Kahale's and two hours before the last set, so there's time for dinner between stops.

The rest of the week heads south. Host Storme Warren records his Exit 209 podcast live at 4 p.m. in the Botero Lounge at Grand Wailea, and it's free to attend. The main event, Songwriters Under the Stars, starts at 7 p.m. on Saturday, Nov. 7, in Grand Wailea's Molokini Garden. It's 21 and over, and doors open at 6 p.m. The ticket page lists The Love Junkies, made up of Liz Rose, Lori McKenna and Hillary Lindsey, along with Riley Green, Randy Houser, Lukas Nelson and special guests. General admission is $35. When last checked, the $60 Preferred seats and the $1,000 VIP tables for up to eight were sold out.

So the festival splits along the South Maui map. The free music is in Kīhei and the ticketed seats are in Wailea.

Saturday night has a choice built in

At 7:30 p.m. on Nov. 7, half an hour after the Grand Wailea concert starts, ProArts hosts Steve Grimes: Greatest Hits. Grimes plays with Steve Sargenti, Dave Fraser, Michael Ferenci and Barney Cortinez, and Pamela Polland and John Cruz are listed as guests. Tickets run $21.20 to $47.70.

So the same Saturday has two songwriter nights in South Maui. One brings Nashville writers to a garden at a resort. The other brings Maui musicians to a room with 110 seats. If the festival's sold-out tiers left you out, Azeka is the other option that night.

The rest of the month at 1280 South Kīhei Road

Every event below comes from the ProArts November calendar. The first Magic in Paradise show, on Nov. 1, has already happened.

The calendar doesn't list a price for the 2 p.m. Enchanted Bookshop show on Nov. 14. Every other performance of it is listed at $10.

Compared with the festival's $35 general admission ticket, most of this calendar costs less. Free Range Comedy is $15.90 and the Thursday comedy showcase is $21.20 flat. The youth show is $10, and the ticket for Hālau Nā Leilehua ʻO Emalia's hoʻike starts at $16. Only Spanksgiving, the night after Thanksgiving, goes higher, with a top tier of $90.10.

The local names keep coming back, too. John Cruz is a guest at the Grimes show on Nov. 7 and returns to headline his own Island Style Series on Nov. 18. David Kuraya, billed as Maui's own magician, has three Magic in Paradise dates on the calendar, one matinee and two evening shows.

Nov. 14 fills Azeka from morning to night

One Saturday shows how much of the month runs through this one parking lot. On Nov. 14, AARP Hawaiʻi holds a free Family Care Pit Stop at Azeka Plaza Makai from 9 to 11:30 a.m. It's a drive-through where caregivers can pick up bags of resources. At 11 a.m., Maui OnStage's Education and Youth Program opens The Enchanted Bookshop inside the playhouse, followed by a 2 p.m. matinee. At 7:30 p.m., comedian Kellen Erskine takes the stage.

That's a caregiver resource event, a children's theater double bill and a comedy headliner at one address in one day. Families with young kids can pair the youth show with the 2 p.m. matinees on Nov. 15, 21 or 22 if the 14th is too crowded.

The free nights are part of the same pattern. The Kihei Community Association holds its public meeting on the third Tuesday of every other month, November included, and ProArts lists the November meeting in the theater on Nov. 17 at 6:30 p.m. at no cost. On Nov. 20, the Trans Day of Remembrance gathering is also free. The room where you see a comedy show on Saturday is also where the community association meets three nights later.

Getting in the door

Parking is in a free municipal lot. Accessible spaces are in front of the theater on the makai side, also free and first come, first served. The box office number is 808-463-6550. With only 110 seats, a popular night like the Saturday bellydance show or the post-Thanksgiving Spanksgiving doesn't have many tickets to go around. Calling ahead or booking online is the simplest way to avoid driving over and finding the show sold out.

If you go to the festival's crawl tonight, the last set at Maui Brewing Co. Kīhei starts at 7:30 p.m. The next 7:30 p.m. start on the ProArts calendar is Saturday, down South Kīhei Road at Azeka.

If you're filling a November calendar for visiting family, or planning a Saturday at Azeka around a show, it's a great idea! You never know what is in store! My husband and I were able to see one of our friends Dr. Gary Greenberg hosts a special evening with his amazing discoveries!