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Strolling Back In Time To Thompson Road

Upcountry Favorite: Thompson Road

The one thing about living on an island like Maui: there are only so many places to go.  It’s actually what I love most about living here.  As we proudly state, “Mauka to Makai” which translates to “Mountain to the Ocean” in Hawaii! Every road and every path eventually leads to a beach, a rain forest, or on top of a mountain like Haleakala.

One of my favorite places on the island to take a leisurely weekend stroll is on Thompson Road. It’s a hidden gem about an hour off the beaten path from the major resort areas like Wailea and Makena. Located in Keokea near the Ulupalakua (a couple miles past upper Kula), it’s about a 3 mile walk round trip with incredible vistas everywhere you look.

Before beginning our walks on Thompson Road, we usually grab a quick coffee or breakfast at Grandma’s Coffee Shop.  Grandmas is famous for their savory pastries and overall lovely upcountry Maui ambience.

Bordered by endless cattle pastures and historic lava rock walls, Thompson Road offers epic views that stretch from the Makena Shoreline all the way to the summit of the Haleakala crater.  There’s some beautiful horses to say hello to, as well as people running and walking their dogs.  Word to the wise: this is an actual road so watch out for the occasional car or truck that drive by, however, we usually see more people on Thompson than vehicles.

Last year my son Gavin and I and had the privilege of meeting one of Maui’s most famous residents Oprah. Oprah actually owns the majority of the property surrounding Thompson road which as you can imagine means it’s some of the most exclusive real estate in Upcountry Maui.  It’s very rare that homes are listed for sale on Thompson Road which adds to the exclusively of the neighborhood.

In addition to Oprah, we usually run into several people we know while walking Thompson Road. This is another thing I love most about living on Maui. It’s such a special place to call home, and we are truly blessed with our great sense of community.

If you’re looking to escape another day by the Wailea Pool or Kaanapali Beach, take a drive up to Thompson.  You’ll be glad you did.

Thompson Road Beauty


Kula Homes For Sale


Price: $5,500,000
Beds: 4
Baths Total: 4
Sqft: 4200
Acres: 2.2998
City: Kula
State: HI
Zip: 96790


Price: $1,395,000
Beds: 3
Baths Total: 2
Sqft: 1296
Acres: 2.408
City: Kula
State: HI
Zip: 96790


Price: $999,000
Beds: 1
Baths Total: 1
Sqft: 696
Acres: 0.5001
City: Kula
State: HI
Zip: 96790

See a complete list of Kula Homes For Sale

Contact A Maui Real Estate Specialist

Please interview me to be your trusted Maui Real Estate and Lifestyle Advisor. I was born and raised on the island, and spend a considerable amount of time to inform my clients about the best deals currently on the market. Please do not hesitate to call me for your Maui real estate needs. I am more than happy to assist you in your home search.


Anthony Sayles R(S) 

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