Makawao, Olinda and Hāli‘imaile
Upcountry Charm, Art, Ranching Heritage & Cool Mountain Breezes
Along the slopes of Haleakalā, Makawao, Olinda, and Hāli‘imaile form one of Maui’s most charismatic and culturally rich Upcountry regions. Known for their cool temperatures, lush landscapes, ranching history, paniolo (cowboy) culture, and vibrant arts scene, these communities offer a refreshing blend of small-town charm and natural beauty.
With scenic country roads, local boutiques, farm-to-table dining, and some of Maui’s most peaceful neighborhoods, this Upcountry trio is perfect for those who want space, serenity, and authentic island living.
Overview
What Makes This Upcountry Area Special
Each community brings its own personality while sharing the same tranquil, breezy, and scenic mountain setting.
Expect:
- Crisp Upcountry air and cooler temperatures
- Rolling hills, tall eucalyptus groves & sweeping ocean views
- Local shops, art galleries, and paniolo heritage
- Quiet country roads and peaceful neighborhoods
- A strong sense of community and creative energy
This region blends rustic charm with a welcoming, artistic spirit.
Makawao
The cultural heart of Upcountry, Makawao is famous for its paniolo history, art galleries, cafés, and charming plantation storefronts.
Loved for:
- Walkable downtown with boutiques & local eateries
- Third Friday town events and art galleries
- Historic rodeo traditions
- Close proximity to schools and parks
Olinda
A peaceful, forested residential area set above Makawao, known for its cooler climate, large lots, and serene privacy.
Highlights include:
- Eucalyptus forests and misty mornings
- Spacious homes and estate-style properties
- Excellent hiking and crisp mountain air
- Quiet, rural living with scenic backdrops
Hāli‘imaile
A small, close-knit community just below Makawao with plantation roots, open fields, and a relaxed country vibe.
Residents enjoy:
- Wide-open landscapes and rural charm
- Convenient access to Makawao & Pukalani
- Local dining gems like Hāli‘imaile General Store
- Quiet streets and laid-back Upcountry living
About
This Upcountry region is known for its handcrafted goods, local cuisine, and creative energy.
Local favorites include:
- Makawao Town: Art galleries, boutiques & paniolo history
- Hāli‘imaile General Store: A renowned farm-to-table restaurant
- Casanova Italian Restaurant: A Makawao institution
- Sip Me Coffee: Cozy café with homemade pastries
- Local farms & produce stands: Fresh fruits, vegetables & island products
Every corner feels authentic and community-focused.
Life in Makawao, Olinda, and Hāli‘imaile is relaxing, artistic, and deeply connected to nature. It's ideal for those who want cooler weather, wide-open spaces, and a tight-knit community feel.
The Upcountry lifestyle includes:
- Morning walks in cool mountain air
- Gardening, farming & backyard orchards
- Art studios, yoga, and wellness-focused living
- Community rodeos, craft fairs & local gatherings
- Easy access to beaches, Kahului, and Haleakalā trails
It’s peaceful, scenic, and wonderfully local.
This region offers a wide range of residential options, from plantation-style homes to modern Upcountry estates.
Real estate features include:
- Spacious lots surrounded by greenery
- Ocean-view and mountain-view homes
- Rural agricultural properties & hobby farms
- Private estates in Olinda’s forested setting
- Charming plantation homes in Hāli‘imaile
- Family-friendly neighborhoods near Makawao town
Buyers appreciate the cooler climate, privacy, and authentic community lifestyle.
Why Buyers Love This Upcountry Area
Buyers are drawn to Makawao, Olinda, and Hāli‘imaile for their peaceful setting, friendly atmosphere, and connection to Maui’s ranching and artistic heritage. With beautiful scenery, cool breezes, and plenty of room to spread out, this region offers a refreshing alternative to coastal living.
