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