When the 98-year-old Historic ʻĪao Theater closes for a new roof, where will Wailuku go to see a play? Until last year the honest answer was that you'd drive somewhere else. Today the answer is a black-box theater on Main Street, a short walk down the road, already in its second season.
That makes this fall unusual. For a few more weeks, downtown Wailuku has two working stages with full programs. After that, Maui's oldest theater starts counting down to a closure of several months. Its newest theater is set to carry the town's theater calendar through it.
Ninety-eight years, 413 seats, and a roof in the county budget
According to Maui OnStage's history of the venue, construction on the ʻĪao Theater began in December 1927 and the doors opened on August 22, 1928. It was built with 702 seats. Today it holds 413. The County of Maui bought the theater and its one-acre site from the Lyons family trust in 1993 for $882,000. Maui OnStage runs the stage. The county owns the building, roof included.
The roof is now a line item. A capital project sheet in the Mayor's proposed FY2027 budget sets aside $3.8 million for the work. Phase 1, in FY2026, covered assessment, design, permitting, and hiring a construction manager. Phase 2, in FY2027, is the renovation itself. The sheet schedules renovation activity from October 1, 2026 through December 31, 2027. It says the work will temporarily disrupt theater operations and will be sequenced to keep that disruption as small as possible.
That window is wide, and the company that programs the theater still doesn't know where in it the closure will fall. Kristi Scott of Maui OnStage explained the uncertainty to The Maui News in September:
"We don't have a date, but we were told it would be within 2027. It's a little hard to program not knowing what's going on."
Scott told the paper that Maui OnStage is looking at alternate venues and expects to lose rental income during the closure. She added, "We're good up through the end of this year."
The second stage is already open on Main Street
The Naylor Theatre explains why a dark ʻĪao matters less to Wailuku in 2027 than it would have a few years ago. The Maui Academy of Performing Arts built it inside the former National Dollar Store building at 2027 Main Street, as part of its Main Street Arts Project campus. Maui Now reported that the first production, Cabaret, ran November 14 to 30, 2025, and that the formal opening and naming came on January 7, 2026. The paper put the project at $15 million. Inside the shell are a flexible black-box room whose stage and seating can be rearranged, plus a lobby, green room, scene shop, storage, and two rehearsal studios.
The two houses work in different ways. The ʻĪao is a 1928 proscenium house with a fixed seat count, and it rents to outside productions between Maui OnStage shows. The Naylor is a room that gets reconfigured for each show, and MAPA uses it as a home base with rehearsal space under the same roof. MAPA calls 2026–27 its second season there. The lineup is Anastasia, A Streetcar Named Desire, The Last Five Years, POTUS, and Hadestown: Teen Edition. Anastasia already ran from August 21 to September 13. With four titles still to come, the Naylor has a full season scheduled through the stretch when the ʻĪao's dates are uncertain.
What's left under the old roof this year
Maui OnStage's 2026 season ended with ʻAinakea, James Nevius's world premiere, which closed October 18. The ʻĪao still has a closing weekend of sorts.
On Friday, October 23 at 7:30 p.m., the theater hosts Witch Perfect. It's a one-night facility rental rather than a Maui OnStage production, and the ticket page shows it as sold out. The Maui News describes it as a live comedy and singing parody of Hocus Pocus with Emmy-winning stars from RuPaul's Drag Race.
The next night, Saturday, October 24, brings Broadway on Maui: A Night at the Masquerade, a collaboration between Wave of Harmony Foundation and Maui OnStage. Tony Award winner Lauren Patten performs with Maui singers. Doors open at 6:30 p.m. and the curtain goes up at 7. Tickets are listed at $25 to $55, with $10 discounts for students and kupuna.
Maui OnStage's big fall event happens away from the theater, and it has already moved once. "Raise the Roof! A Sneak Peek Fundraiser" was set for September 26. The company postponed it as a storm approached Maui, and the new date is Saturday, November 21, from 5 to 8 p.m. at Ocean Organic Vodka Farm & Distillery in Kula. Tickets are $225, and tickets and pledges from the original date carry over. The listing describes a dress code of resort casual with construction-themed touches, like "blueprints and boat shoes, safety goggles and sundresses, high-vis alohawear." According to The Maui News, guests can guess the company's next season from clues hidden in the décor and costumes, and the closest guess can win season tickets. So the clearest preview of how Maui OnStage plans to program around the roof work will come at a farm in Kula, not from the stage on Market Street.
Streetcar takes over the calendar after Halloween
After Broadway on Maui, the busiest theater stretch in downtown Wailuku is on Main Street. MAPA's A Streetcar Named Desire runs November 20 through December 6 at the Naylor. MAPA flags mature content and recommends it for ages 13 and up. Tickets are listed at $17.50 to $45. On the two "Mahalo Saturday" performances, every seat is $25.
| Date | Time | Event | Venue |
|---|---|---|---|
| Fri., Oct. 23 | 7:30 p.m. | Witch Perfect, listed sold out | ʻĪao Theater, 68 N. Market St. |
| Sat., Oct. 24 | 7 p.m. curtain | Broadway on Maui with Lauren Patten | ʻĪao Theater |
| Fri., Nov. 6 | Evening | Wailuku First Friday | North Market Street |
| Fri., Nov. 20 | 7:30 p.m. | Streetcar opening night | Naylor Theatre, 2027 Main St. |
| Sat., Nov. 21 | 7:30 p.m. | Streetcar, Mahalo Saturday, all seats $25 | Naylor Theatre |
| Sat., Nov. 21 | 5 to 8 p.m. | Raise the Roof fundraiser | Ocean Organic Vodka Farm & Distillery, Kula |
| Sun., Nov. 22 | 3 p.m. | Streetcar matinee | Naylor Theatre |
| Fri. and Sat., Nov. 27 and 28 | 7:30 p.m. | Streetcar, Nov. 28 is Mahalo Saturday | Naylor Theatre |
| Sun., Nov. 29 | 3 p.m. | Streetcar matinee | Naylor Theatre |
| Fri. and Sat., Dec. 4 and 5 | 7:30 p.m. | Streetcar | Naylor Theatre |
| Sun., Dec. 6 | 3 p.m. | Streetcar closing matinee | Naylor Theatre |
November 21 is the night the town's two theater companies overlap. Maui OnStage is raising money upcountry for the ʻĪao's future, and MAPA is running its cheapest Streetcar performance on Main Street, both on the same Saturday. The Maui OnStage site lists First Friday on November 6. That's a street event on North Market Street, so it carries on whatever the theater's roof schedule turns out to be.
Parking and dinner around curtain time
An evening downtown runs on the same few blocks whichever theater you're headed to.
- Wailuku Garage, 30 N. Church St. The first floor is open to the public, and the upper floors are for permit holders. Park Maui lists Hawaiʻi residents' first two hours as free, then $1 an hour. Visitors pay $1 an hour, up to $10 a day.
- ʻĪao Theater lot, 70 N. Market St. This free public lot has 39 stalls with a two-hour limit, posted for Monday through Saturday, 8 a.m. to 6 p.m.
- 808 on Main stays open until 8 p.m. Thursday through Saturday, closes at 4 p.m. Monday through Wednesday, and is closed Sunday. That works for an early dinner before a Friday or Saturday show. It won't help before a Sunday Streetcar matinee.
- Umi Sushi, 1440 Lower Main Street, serves dinner from 5 to 9 p.m., Wednesday through Saturday.
The parking hours and restaurant hours above are what each business currently posts, so check before a big night out. Sometime in 2027 the stage that opened on August 22, 1928 will go dark while its roof is replaced, and Wailuku's theater calendar will run out of a converted dollar store a short walk down Main Street.
Some of the best moments of living in Wailuku happen on Market and Main Street on a Saturday night. If you're thinking about how the ʻĪao roof project and the new Naylor Theatre might change downtown over the next year, I'm always happy to talk it through. Rai Morimoto grew up with these blocks and would love to hear what you're seeing there. Let's Connect.
