October on Maui opens with the smell of fair food drifting over Wailuku and closes with keiki in costume on the MACC lawn. In between, the island fills with hula, rodeo, world-class windsurfing at Hoʻokipa, and Festivals of Aloha gatherings stretching from Lānaʻi to Hāna. Here's what's happening this month.

99th Maui County Fair

Thursday, October 1 – Sunday, October 4

War Memorial Special Events Complex, Wailuku

The fair is back for its 99th year, and it remains one of the few weekends when the whole island seems to show up in one place. Expect rides, ʻono food booths, live music, and livestock and horticulture exhibits, plus contests that pull in everyone from keiki to kūpuna. Before you head over, check the Maui County Fair site

We're delighted to welcome home Phillip Chiesa to Island Sotheby's International Realty, where he continues to bring dedication to every client relationship. For Phillip, real estate is about understanding each client's goals, solving complex challenges, and helping people make confident decisions during one of life's biggest milestones. When he's not working with clients, you'll likely find him exploring Maui's incredible landscapes, climbing at the local rock gym, or enjoying the peaceful beauty of ʻĪao Valley.

Get to know Phillip as he shares more about his journey, what he loves most about Maui, and the philosophy that guides his approach to real estate.

What led you to where you are today?

I started my real estate career at 24 with,

Caring for the landscape that defines this special part of Maui

Along the slopes of Haleakalā, the character of Upcountry Maui is closely connected to its forests, open spaces and watersheds. Across the region, local organizations and volunteers are helping care for these places through native habitat restoration, education and hands-on stewardship.

One of the most visible efforts is taking place in Kula, where the Kula Community Watershed Alliance emerged following the August 2023 Kula fire. What began as a response to the affected landscape has grown into a long-term effort focused on restoring native habitat and supporting a healthier, more resilient watershed.

Restoration takes hold

The work goes well beyond replanting. The Alliance

For Shannon, real estate has always been about people. Born and raised on Maui with deep roots in Lahaina, Shannon understands this is what makes the island such a special place to call home. She's committed to making the process feel approachable, informed, and personal for every client — first-time homebuyers, growing families, and those searching for their own piece of paradise alike.

Get to know Shannon as she shares more about her journey, what inspires her, and why she loves helping clients navigate Maui real estate.

What led you to where you are today?

I've been licensed in Hawaiʻi real estate since 2013 while also building a career in the hospitality industry, where I spent many years managing sales and marketing operations. Balancing

September settles into Maui like a long exhale. The kids are back in school, the visitor crowds thin out just enough to notice, and the island seems to trade its summer hustle for something quieter and more local. It's the kind of month when a Friday night in Kīhei or a Saturday morning in Keokea feels less like an event and more like a homecoming. Here's where to find the aloha this September.

Sunset Tunes ft. Ron Kuala'au

Friday, September 4, 2026 · 6:30–8:00 pm

Kalama Park Bandstand, Kīhei

Maui County's free live music series closes out its short 2026 run with local musician Ron Kuala'au taking the south-end bandstand as the sky over Kīhei fades to pikake pink. Bring your low-back chairs, a blanket, and something cold to sip, and

Ask anyone what they picture when they hear "West Maui," and you'll get the same postcard answer. Golden sand. Golf greens. Sunset mai tais on a lanai. All true. All wonderful. And we're not complaining. But it's also barely scratching the surface.

Because tucked behind the resorts and beach paths is a West Maui most people, kamaʻāina included, have never really met. Manta rays gliding just offshore. A mountain rainforest few will ever set foot in. A waterfall taller than most skyscrapers, hiding in plain sight above the golf courses. Here's a look at the West Maui that exists just past what everyone already knows.

The ocean here holds more than you'd guess

Most people driving past Olowalu see a quiet stretch of coastline between Lahaina

August on Maui moves at its own unhurried pace — obon drums echo from Lahaina to Lānaʻi, Upcountry ropers dust off their saddles, and our own Island Sotheby's International Realty Kapalua office has a new artist in residence filling the space with color. Here's where to find the month's best gatherings, from a Friday night town party to an evening with a Grammy-winning songwriter.

Jules Trowbridge, Artist in Residence at Island Sotheby's Kapalua

Mondays 9:00 am – 1:00 pm & Fridays 2:00 – 5:00 pm, throughout August

Island Sotheby's International Realty, Kapalua office

Our Island Sotheby's International Realty Kapalua office has a new artist in residence this month: Maui fine artist Jules Trowbridge, known for bold, emotionally

Photo: Musician, Sunny Kalama

South Maui has always had a rhythm of its own. Maybe it’s the sound of waves rolling into the shoreline, the golden glow of sunset over the ocean, or the way island life naturally slows people down enough to enjoy the moment. 

One of the many perks of living in South Maui is that live music is never far away. Whether you’re looking for a sunset cocktail with a view, a casual evening with local food and island tunes, or a special cultural experience, there are plenty of ways to enjoy the sounds of Maui.

Here are some favorite places to experience live music in South Maui.

Monkeypod Kitchen | Wailea

A longtime South Maui favorite, Monkeypod Kitchen in Wailea is the perfect spot to enjoy local music,

July on Maui moves in two speeds: full tilt over the Fourth of July weekend, then a slower, more local rhythm for the rest of the month. Between upcountry rodeo dust, a long-awaited blessing on Front Street, and a steady run of live music in Kihei, there's a reason to get out most nights. Here's what's worth circling on the calendar.

Blessing for Front Street Railing & Walkway Project

Wed, Jul 1, 2026, 3–4pm

700 block of Front Street, Lahaina (between Lahainaluna Rd & Dickenson St)

Lahaina marks another milestone in its wildfire recovery with a community blessing for the newly completed Front Street Railing and Walkway Project. The work rebuilt roughly 1,450 feet of sidewalk and 700 feet of stainless-steel, ipe-topped railing along the

There's a shift happening in the way people think about their next home — and it's not about square footage or finishes. It's about time.

Not how long the escrow takes. How long they plan to stay. How well a home will serve them not just this season, but a decade from now, and the decade after that. The luxury buyer of 2026 isn't just acquiring property. They're making a decision about how they want to live — and for how long.

Sotheby's International Realty's 2026 Mid-Year Luxury Outlook, released this month, puts a name to what we've been watching unfold here on Maui: longevity is the new luxury. Wellness infrastructure, health-centered design, and the ability to age gracefully in a place you love are now primary drivers for high-net-worth