Drive Kamehameha Highway past Windward Mall and you have watched a decade of retail turnover happen in slow motion. Sears went dark in 2019. Macy's followed in 2023, then came down entirely in a demolition the following year. If you were reading the mall by its storefronts alone, the story looked like decline: two anchor tenants gone inside four years, empty pads sitting where department stores used to be.
That is the wrong data to be tracking. While the anchor spaces sat vacant, the thing actually pulling people through the doors was quietly becoming the best of its kind in the state.
The market grew while the mall churned
The Plenty of Aloha Farmers Market has been running inside Windward Mall since 2011. It is still the only indoor, air-conditioned farmers market in Hawai'i, with vendor tables spread across both levels of the mall rather than confined to a parking lot. That indoor setup matters more on the windward side than almost anywhere else on O'ahu. The Ko'olau range wrings rain out of the trade winds most afternoons, and a covered, climate-controlled market means Wednesday and Sunday shopping doesn't depend on the weather cooperating.
Those are the two days it runs: Wednesdays from 2 to 6 p.m. and Sundays from 10 a.m. to 2 p.m., in Center Court. More than 50 vendors set up on a given day, and the mix leans toward actual farms rather than resold produce, which is part of why regulars keep coming back even as individual vendors rotate in and out over the years.
In late 2024, the market marked its 15th anniversary. Around that same milestone, the American Farmland Trust recognized it as the number one farmers market in Hawai'i for the second year running, and ninth in the country out of more than 1,500 markets that participated in the national celebration, drawing close to 97,000 votes. That ranking landed in the same stretch of years when Macy's was closing and its building was being torn down. The mall's traditional retail identity was contracting at the exact moment its market identity was becoming a statewide talking point.
If you have shopped the market recently, you already know some of the names that make it worth the trip. Da Pupu Bros show up with smoked marlin dip and ahi jerky. Hawaii Bake Shop brings butter garlic truffle chips. On a rainy Wednesday evening, Haole Baking Co. has built a following for spanakopita and baklava sold out of a stand most people find by accident, drawn in by the name before the pastries convince them to stay. Regulars still talk about the lilikoi butter and the pipikoa, the kind of specifics that don't show up on a chain grocery shelf.
What actually replaced the anchor stores
The retail side of the story isn't empty, it just isn't retail in the traditional sense anymore. Target opened in the former Sears space in 2022, filling that footprint with a full grocery and general merchandise format built for the neighborhood. The Macy's site took longer. After the building came down in early 2024, a new anchor structure went up specifically to house new tenants, and Planet Fitness opened there in late 2025.
Line up the timeline and the pattern is clear:
- 2019: Sears closes after decades as an anchor tenant
- 2022: Target opens in the renovated Sears space
- 2023: Macy's, originally a Liberty House location, closes
- Early 2024: The former Macy's building is demolished
- Late 2025: Planet Fitness opens on the same footprint as a purpose-built anchor space
Neither replacement store restores the department-store version of the mall. What they do is turn Windward Mall into a building people pass through for groceries and workouts on their way to or from the market, the movie theater, or one of the smaller shops still filling out the directory. The mall's gravity shifted from "destination for department store shopping" to "errand stop that happens to have a nationally ranked farmers market at its center." That's a different business, and arguably a more durable one for a neighborhood mall on the windward side, where big-box department stores were never going to be the draw that pulled people off the highway.
Two night markets, same address, different rhythms
The mall's parking lots do double duty after dark, and this is where a lot of residents mix up which event is which. There are two separate night markets tied to the Windward Mall address, and they run on entirely different schedules.
| Event | Frequency | Hours | Location |
|---|---|---|---|
| Koʻolau Night Market | Every second Friday of the month | 5 to 9 p.m. | Windward Mall parking lot, Kamehameha Highway side |
| Kaneohe Night Market | Once a year, in June | 4 to 9 p.m. | 80,000-square-foot lot on Alaloa Street, across from the mall |
The Koʻolau Night Market, run by Island Craft Fairs, is the recurring one. It's smaller in footprint but shows up like clockwork twelve times a year, built around food trucks and local artisan vendors in the lot facing Kamehameha Highway. If you've stumbled onto pupus and retail tables in that parking lot on a random Friday evening, that's what you found.
The Kaneohe Night Market is a different animal entirely, billed as the town's biggest festival and staged just once a year on a much larger stretch of land across the street. It's the kind of event people plan around rather than one they catch by accident on a Friday drive home, and mixing the two up means showing up to the wrong lot on the wrong night, or missing the annual one because you assumed it was just another Koʻolau Friday.
What this means if you live here
None of this changes what Windward Mall looks like from the highway, and it's not trying to be a department store destination again. What's changed is which part of the property is actually earning the neighborhood's loyalty. The farmers market didn't just survive the anchor closures, it kept climbing rankings through them, and the businesses that filled those empty footprints, Target for groceries, Planet Fitness for fitness, are built around routine visits rather than occasional big purchases.
For a longtime resident, the practical takeaway is simple: the market's schedule (Wednesday afternoons, Sunday mornings) and the Koʻolau Night Market's second-Friday rhythm are the two dates worth keeping on a calendar. The bigger annual Kaneohe Night Market is worth checking for separately each June rather than assuming it repeats monthly like its smaller counterpart.
The mall's recent history is a useful reminder that a shopping center's health isn't always visible in which anchor stores are open. Sometimes it's visible in what people are still driving there for on a Wednesday afternoon, rain or shine.
If you're thinking about buying or selling on the windward side and want a read on how a neighborhood's daily rhythms shape its long-term value, Team Hawaii knows Kaneohe block by block. Let's Connect.
