Two Stages, a Few Blocks Apart: What's Playing in Wailuku Town This Fall

"It happens to have my family name on it," Susan Naylor told Maui Now in January. "But it belongs to the community."

She was standing at 2027 Main Street, in front of the theater the Maui Academy of Performing Arts had spent nearly a decade building. The Naylor Theatre was formally named and opened on January 7, 2026. Before that, MAPA had already put on nine performances of Cabaret there, from November 14 to 30. Around the corner on Market Street, Maui OnStage still runs the Historic ʻĪao Theater at 68 N. Market St. That gives Wailuku two working stages within a few blocks, and this fall's calendar shows what that means. Something is on almost every weekend from now until early December.

The second stage changed how the town books its year

The Naylor is no small rehearsal room. It's a 12,000-square-foot, $15 million facility. MAPA started the project in 2016. In 2022 Susan Naylor pledged $1 million, and other donors followed. Carolyn Wright, MAPA's executive director, said most donors to the nonprofit had given between about $100 and $10,000, so a gift that size was "really unheard of for us."

The public got its first real look on April 3, at Wailuku First Friday. That night the Naylor ran guided tours every 10 minutes from 6 to 8 p.m. and showed people rehearsals for MAPA's production of Frozen.

You could see the two-stage idea working by June. The first Wailuku Film Festival ran five days, June 17 to 21, with screenings at both the Historic ʻĪao Theater and the Naylor. Pacific Media Group presented it as a Maui Film Office initiative, with support from Maui County. That's one festival moving audiences between two venues on the same streets. Before the Naylor opened, that couldn't happen in this town.

October is Market Street's month

The headline show this month is a world premiere. Maui OnStage opened ʻAinakea on Friday, October 2. It's a new play by Maui playwright James Nevius, set in West Maui in 1953. A family that owns a sugar plantation is running out of money, and as people gather to decide what happens to the estate, the play asks who should take care of the land. It's inspired by Chekhov's The Cherry Orchard and directed by Francis Tauʻa, with a Maui cast and crew.

The set is worth getting there early to see. Scenic designer Amanda Dellinger based it on the Hanakaʻōʻō ahupuaʻa in Kāʻanapali. The backdrop follows the outline of the West Maui mountains above the old Puʻukoliʻi Village camp. She also used three colors from Ameritone-Maui's Lahaina Restoration Foundation historic color palette, in memory of two historic Lahaina buildings lost in the wildfires.

ʻAinakea runs through October 18. Friday shows start at 7:30 p.m., and Saturday and Sunday shows start at 3 p.m. Tickets cost $10 to $45. Nevius does a "Talk Story with the Playwright" after the Sunday shows on October 4 and October 11. If today's talk is too short notice, next Sunday is the last one.

The ʻĪao has more going on this month than ʻAinakea. Here's what's booked in both buildings from now through early December:

Look at Saturday, October 17. ʻAinakea has its 3 p.m. matinee, and then Fighting Like Mad goes up at 7:30 in the same building. Collective Pilina Theatre, Maui Medic Healers Hui and AHAS are presenting it as a facility rental, and reservations are free. Witch Perfect on October 23 is also a rental, and it's already sold out. For Broadway on Maui the next night, students and kūpuna get a $10 discount.

Once October ends, the ʻĪao's website has nothing else posted at the theater this year. Maui OnStage's "Raise the Roof" fundraiser, now moved to November 21, takes place at Ocean Vodka, not on Market Street.

In November, the action moves to Main Street

That's when the Naylor's turn comes. MAPA's 2026–27 season lists one fall show, Tennessee Williams' A Streetcar Named Desire, directed by Sally Sefton, running November 20 to December 6. MAPA's season page said tickets would go on sale in early October. When I checked, the show page didn't have performance times or prices yet. If you want a particular weekend, the season page at mauiacademy.org is the place to watch.

Wailuku First Friday fills the gap between the two theater seasons. The next dates are November 6 and December 4, from 6 to 9 p.m. on Market Street. The November date lands two weeks before Streetcar opens, and December 4 falls on its last weekend. You can walk the street fair and catch the play in the same week without ever leaving town.

Plan your night around 6 p.m.

The stages run into the evening. Much of the town core keeps daytime hours, and that's what shapes a show night. Wailuku Coffee Co. at 26 N. Market St. is open 7 a.m. to 5 p.m., and 7 a.m. to 2 p.m. on Sundays. It's an easy stop before a weekend matinee, but it won't be open before a Friday curtain.

These are the nearby places I could confirm serve dinner, from their own published hours:

• The Parlay, 2086 Main St.: Monday through Saturday, 11 a.m. to 11 p.m., and Sunday 10 a.m. to 9 p.m. It's the one option that stays open after a 7:30 show lets out.
• 808 Old Town Bistro, 2051 Main St.: open until 8 p.m. Thursday through Saturday, closes at 4 p.m. Monday through Wednesday, and closed Sundays.
• Tasty Crust, 1770 Mill St.: 6 a.m. to 8 p.m. Tuesday through Sunday, closed Mondays.

So for a Friday at 7:30, 808 Old Town Bistro and Tasty Crust both work if you eat around 6 and walk over. For the Monday performance of Bright at 6:30 on October 5, The Parlay is the confirmed choice, since 808 Old Town Bistro closes at 4 on Mondays and Tasty Crust is closed.

Parking runs on the same clock. At the Wailuku Garage, 30 N. Church St., the first floor is open to the public and the main entrance is on Church Street. The $1-per-hour rate applies from 8 a.m. to 6 p.m. every day. The ʻĪao Theater lot at 70 N. Market St. is still free. It has a two-hour limit, and its 39 public stalls are only open to the public from 8 a.m. to 6 p.m., Monday through Saturday. Two hours in that lot won't cover a weekend matinee plus a stop for coffee. The garage is the easier choice for a 3 p.m. show.

First Fridays have their own rules. Market Street closes to cars at 5:30 p.m., and any vehicle still parked there gets ticketed and towed. The organizers advertise free parking after 6 p.m. in the Wailuku Municipal Parking Garage, with access from Church Street between Vineyard and Main.

Here's how a Saturday matinee can play out:

1. Park in the Wailuku Garage off Church Street a little after 1 p.m. at the $1 hourly rate.
2. Get coffee at Wailuku Coffee Co. on N. Market St. before it closes at 5.
3. See ʻAinakea at 3 p.m. at the Historic ʻĪao Theater. On October 17, you could stay in town for Fighting Like Mad at 7:30.
4. Have dinner at 808 Old Town Bistro before 8, or at The Parlay if you want to linger.

I've watched Wailuku's town core change for a long time, and having two stages within a few blocks is new. If you're thinking about how a walkable spot near Market and Main fits into your own plans, whether that's selling, staying put, or making a change, Lena Taberna is glad to talk it through. You can also start with a free home valuation.