Aloha friends! This weekend has a little something for everyone on Maui, from Friday night music with Sheryl Renee and Judy Collins to a free family art day at the MACC, Sunday laughs at ProArts, and big open-ocean energy with the Pailolo Challenge. Whether you are looking for live entertainment, something fun with the keiki, or just want to cheer on the paddlers, here are a few happenings to keep on your radar for September 18–20.
Sheryl Renee Birthday Concert & Party
If you are looking for a fun Friday night out, this should be a good one. Sheryl Renee brings big vocals, live music, special guests, audience requests, and plenty of room to dance. Showtime is 7:30 pm at ProArts Playhouse in Kihei. Tickets and details are available through ProArts Playhouse.
Judy Collins
Also on Friday night, folk legend Judy Collins brings her Sweet Judy Blue Eyes Farewell Tour to Castle Theater at the Maui Arts & Cultural Center. If her music has been part of your soundtrack over the years, this is a special chance to hear that voice and those stories live on Maui. Showtime is 7:30 pm, and patrons are asked to bring non-perishable items for the Maui Food Bank. Tickets and details are available through Maui Arts & Cultural Center.
Observe and Play Family Day
Saturday morning at the MACC is a great pick for families. Observe and Play Family Day returns to Schaefer International Gallery at 10 am with hands-on art activities inspired by Keoni of Hawai‘i: Art of the Aloha Shirt. Come dressed in your aloha wear, check out the colorful designs, and let the keiki jump into creative stations like mini-shirt printing, mu‘umu‘u design, fabric patterns, and family photos. It is free, with no pre-registration required. Details are available through Maui Arts & Cultural Center.
Standup Comedy Showcase
Sunday night brings an easy way to wrap up the weekend with some laughs at ProArts Playhouse in Kihei. The Standup Comedy Showcase starts at 7 pm and features a lineup of local and visiting comedians for a 90-minute show. Tickets and details are available through ProArts Playhouse.
Japengo Omakase Experience
For those seeking a truly unique dining adventure this weekend, consider reserving the Japengo Omakase Experience at the sushi bar in Japengo. Chef Masa Hattori curates a special eight-course menu featuring fresh local seafood and seasonal ingredients, prepared and presented with care. Experience limited to 6 guests on Saturdays from 6 – 8 pm. Tickets $270 and prepaid reservation required.
MCHCA Long Distance Season
Long Distance Season reaches its big September highlight this weekend with the 2026 Nalu’s South Shore Grill Pailolo Challenge on Saturday, September 19. Hosted by Hawaiian Canoe Club, this 26-mile downwind race crosses the Pailolo Channel from Honokahua Bay at D.T. Fleming Beach on Maui to Kaunakakai, Molokaʻi. The channel is known for strong wind and open-ocean conditions, so crews will be putting all that endurance-season training, timing, and teamwork to the test. Check out Hawaiian Canoe Club for the Race Schedule and visit the Pailolo Challenge site for race details.
Anything Else This Weekend or Next?
I am always looking to promote other weekend activities for Maui organizations. If we are missing anything, drop me a line any time for future happenings. Mahalo!!!
Real Estate
Latest Maui Figures
As of September 10th, Maui County has 218 pending transactions and 1613 active down to 11.9%. We’d held over 12 consistently for several weeks recently. Hopefully, we head back up and can stick the 13s and continue to increase this figure.
Hot Listings
I have been busy working on a project that will be coming to market soon. 20 acres of ocean view organic farmland in Waiehu! I’m so excited to share Kuawa Olu with you all. Stay tuned!
If Kuawa Ola isn’t for you, here is a nearby listing that we at Hawaii Life also represents
Lower Waiehu Beach Road has MLS 406777 closer to the beach. 5-bedroom home with 2-bedroom ohana across street from the ocean. Great 2 story home has been a successful investment property. It would also be a great owner-occupied home offering easy beach access for nearby surfing, fishing, strolls. Close to everything in town. It’s a great area.
I am here to go over latest figures and discuss your plans for Real Estate on Maui.
About Me
As a lifelong Maui resident and realtor with over 20 years of experience, I have a profound understanding of Maui’s Real Estate market. My extensive expertise helps me meet your needs whether you are buying or selling a home, investment property, or conducting large transactions. I enjoy water sports, Jiu-jitsu training, soccer, rugby, family time, and socializing.
If you have questions about Maui’s Real Estate market, your equity, options, or need assistance with any real estate matters, feel free to call, text, or email me. I’m here to help!
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