October On Maui: Fall Festivities and Island Adventures

October on Maui is truly unmatched! From picturesque oceanfront pumpkin patches to world-renowned food and wine festivals, there is no shortage of vibrant events and experiences. Whether you want to soak up the autumn sunshine or savor the finest local cuisine, there's no shortage of unforgettable moments waiting for you this season.

1. Kula Maui Pumpkin Patch

When: Month of October 9am-4pm daily 

Kula Farms' Pumpkin Patch is a beloved fall tradition nestled in the cool, rolling hills of Upcountry Maui - only available during the fall season! This annual event offers locals and visitors alike the chance to pick the perfect pumpkin while enjoying fresh produce, local food vendors, and farm-fresh treats. Beyond pumpkins, Kula Farms showcases the beauty of Maui’s coastline, with colorful flower fields and cool breezes.  It’s the perfect escape for a fun-filled day in the heart of Maui's countryside! Starting 10/1 Kula Farms is open from 9am-4pm daily. 

2. Annual Ukulele Festival 

When: October 27th at 2:00pm 

Mark your calendars for Maui's 17th Annual Ukulele Festival, happening on October 27th at the Maui Arts & Cultural Center (MACC). This family-friendly event promises a laid-back afternoon filled with some of the islands finest Hawaiian music including the world-renowned Jake Shimabukuro, virtuoso Derrick Sebastian, and the legendary Benny Uyetake. Whether you're a longtime fan or new to the music, this is an unforgettable opportunity to experience the soulful and vibrant spirit of Hawaiian culture. Best of all, the Ukulele Festival is completely free. 

3. Hawaii International Film Festival 

When: October 19-20th 

As the premier cinematic event of the Pacific, the 44th HIFF Fall Festival, presented by Halekulani, promises an exciting lineup of feature and short films from around the globe, with a spotlight on Asia, the Pacific, and homegrown Hawai‘i productions. A must-attend for renowned industry professionals, up-and-coming filmmakers, and film lovers alike, HIFF is where creativity comes to life on screen. On Maui, catch in-theater screenings October 19-20. 

4. Explore Historic Wailuku Town 

A visit to Wailuku Town offers a glimpse into Maui's rich history and vibrant local culture. Nestled at the base of the West Maui Mountains, this charming town is the gateway to one of the island’s most treasured natural wonders—ʻĪao Valley State Park. Explore lush trails and marvel at the towering ʻĪao Needle, a striking rock formation surrounded by dense rainforest, streams, and breathtaking views. After soaking in the beauty of ʻĪao Valley, head back to Wailuku’s quaint streets to discover its unique blend of old Hawaiʻi charm and modern flair. Stop by Esters Fair Prospect, a local favorite offering a creative menu of craft cocktails and delicious small plates, perfect for unwinding after a day of adventure. With its thriving art scene, historic landmarks, and local boutiques, Wailuku Town is a must-visit for anyone looking to experience authentic Maui.

5. Maui Food and Wine Festival 

When: October 25th-27th 

The Maui Food and Wine Festival is a celebration of the island’s vibrant culinary scene, bringing together top chefs, world-class winemakers, and food enthusiasts for an unforgettable experience. Set against the stunning backdrop of Maui’s beaches and mountains, this annual event showcases the best of local Hawaiian ingredients, paired with fine wines from around the globe. Whether you're indulging in a gourmet tasting menu, attending a cooking demo, or savoring a wine pairing, the festival offers a chance to explore Maui’s rich culinary diversity while enjoying the island’s signature hospitality. Perfect for food lovers and wine connoisseurs alike, it's a feast for all the senses.

October in Maui is brimming with activities that showcase the island’s unique culture, breathtaking landscapes, and vibrant community spirit.  Let us help you find the perfect home for your next vacation so you don’t miss out on any of these incredible experiences! Contact our team directly at rezinq@mauiresortrentals or start searching our collection of luxury vacation rentals now on our site.