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Thompson Road, Kula: The Walk, the History, and Living Upcountry

Posted by benjamen.harper@gmail.com on July 24, 2022
Hawaii Attractions & Activities
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Thompson Road is a quiet country road in Keokea, at the upper end of Kula on Haleakala’s western slope, and it’s one of the best easy walks on Maui. It runs through ranch pasture with long views down to the south Maui coast. Most people go for the view. Some of them end up looking at land for sale nearby.

A lot of what’s written online about the road’s history doesn’t hold up. You’ll find claims that it was built in a specific year by a specific person. We couldn’t find any record that backs that up, so it isn’t repeated here. What follows is what can actually be sourced: where it is, what the walk is like, a bit of real Keokea history, and what to know if you’re thinking about living Upcountry.

Where it is

Keokea is a small community past upper Kula on the way toward Ulupalakua. It sits at roughly 2,860 feet, and the 2020 census counted about 2,200 people there. Thompson Road leaves the highway area near Kula Hospital, and that’s where most walkers park and start.

From Wailea or Makena it’s close to an hour’s drive up the mountain. It’s a different climate up there: cooler, often breezy, and clouds tend to build over Kula in the afternoon.

The walk

It’s a paved, public road, not a trail. An out-and-back is about 3 miles round trip. The road rolls gently through cattle pasture lined with old lava rock walls, and you’ll usually see horses and cows along the way. The view stretches from the Makena shoreline up to the summit of Haleakala.

Thompson Road, Keokea, Upcountry Maui
Thompson Road, Keokea, Upcountry Maui
  • Go early. There’s very little shade. Early morning is cooler and clearer. Late afternoon can be nice too, but the clouds often roll in.
  • Watch for cars. It’s a working road with ranch trucks and residents. Walkers often outnumber cars, but there’s no sidewalk.
  • Stay on the road. The pasture on either side is private land. Don’t climb the walls or open gates.
  • Bring a layer. At nearly 3,000 feet it can feel cool in the morning even when it’s hot at the beach.

What history we can actually confirm

We couldn’t find a published source that says who Thompson Road is named after or when it was built. There is a long-running, family-run Thompson Ranch on Haleakala’s slopes that offers trail rides, and it’s tempting to connect the two. Nothing we found confirms it, so treat any confident origin story with suspicion.

Keokea itself has a well-documented history. It was a center of Maui’s Chinese community in the late 1800s and early 1900s. Sun Mei, the older brother of Chinese revolutionary leader Sun Yat-sen, came to Hawaii in 1871 and ran a large ranch in Keokea. Sun Yat-sen sent his mother, wife and children there for safety, and visited from time to time. Sun Mei sold cattle from the ranch to help fund his brother’s early revolutionary work. The family sold the ranch in 1908, and it later became part of Haleakala Ranch.

Part of Keokea is also Hawaiian Home Lands, set aside for native Hawaiian homesteaders. Those lots aren’t sold on the open market.

Living in Keokea and Kula: what buyers should know

People fall for Upcountry because of the air, the space and the views. It’s ranch country, mostly larger lots, and homes near Thompson Road don’t come up often. A few things matter more here than almost anywhere else on Maui.

Water. This is the big one. Maui County stopped taking new applications for Upcountry water meters on January 1, 2013. As of late 2025 there were about 1,424 applicants on the waitlist, asking for 3,612 meters, and some people have waited more than 20 years. The county says the Upcountry system can’t reliably meet existing peak demand. It’s working on new filters at the Kamole treatment plant, new reservoirs and several new wells, but the larger pieces are years out. For a buyer, that means a home or lot with an existing county meter is worth a lot more than one without. On any vacant land, ask first whether there’s a meter, and if not, how water would get there (catchment, a private well, or nothing realistic).

Wildfire. On August 8, 2023, the same day as the Lahaina fire, a fire in Kula burned about 202 acres and destroyed 17 homes, and a separate Olinda fire burned about 1,081 acres and three homes. Dry grass and strong winds are a real risk Upcountry. Before buying, look at defensible space around the house, road access in and out, and, most important, whether you can get homeowners insurance and at what price. Get a quote early in escrow, not at the end.

Climate and commute. Upcountry is cooler and greener than the coast. Nights can get genuinely cool, which surprises people moving from the coast. The tradeoff is distance: shopping, the airport and the beaches are all a drive down the mountain, and from Keokea that drive is longer than from Pukalani or lower Kula.

Prices. Maui’s island-wide median single-family price was $1,165,000 in July 2026, down about 11% from a year earlier, according to REALTORS Association of Maui data. Upcountry sales are thin, often just a handful a month, so a single sale can swing the numbers.

FAQ

Is Thompson Road open to the public? Yes, it’s a public road. The land along it is private, so stay on the pavement.

How long is the walk? About 3 miles out and back, with gentle grades. Most people take an hour or so, longer if they stop for photos.

Can I buy a lot in Kula and build? Possibly, but check water before anything else. Without an existing meter, building can be slow, expensive or not practical.

Is Kula still recovering from the 2023 fire? The burn area was small compared to Lahaina. For buyers, the lasting effect is mostly on insurance availability and cost, so get quotes early.

Questions about buying or selling in Hawaii? Call or text 808-866-6593, or start here →

Sources

General information as of October 2026, not legal, insurance or water-rights advice. Water meter availability and insurance terms change; confirm them for a specific property before you buy.

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