The Deal With Oprah Winfrey’s Private Maui Road

By Anthony Pignataro

According to Forbes, Oprah Winfrey is worth $2.7 billion. The 57-year-old former actor became famous for her Oprah Winfrey Show (which ceased production in May) but still runs a vast media empire. She owns a production company (Harpo Productions), a cable network (OWN), a magazine (O), and the Oprah Radio satellite station. She also owns estates in Montecito, California and Fisher Island, Florida; houses in Lavallette, New Jersey, Douglasville, Georgia and Telluride, Colorado; and assorted properties on the islands of Antigua and Maui. The latter includes 100 acres in Hana, 1,000 acres Upcountry (which boasts a small, terribly exclusive 12-room bed and breakfast) and a four-mile road.

And not just any road, either: Oprah’s road is concrete and asphalt 12 feet across. Goodfellow Brothers paved it in December 2010. The road stretches from the water tank at Kealakapu Road near Piilani Highway in Kihei to Keokoa, near Haleakala Highway. It’s a road locals have been waiting for 40 years — a potentially golden road that could radically ease traffic congestion in Central Maui.

That is, if the public could use it, which it most certainly cannot. “The paved road, drainage swales and detention ponds will be privately maintained,” stated a June 2009 Drainage Report on the effects of paving the road prepared by Wayne I. Arakaki Engineer LLC for OW Ranch, LLC, (the initials reportedly stand for “Oprah Winfrey”) and kept on file with the Maui County Planning Department. “This is a private roadway and will not be open to the public.”

OW Ranch paid for the road. “It wasn’t cheap,” said OW Ranch agent Hugh Starr when asked how much it cost. He ultimately declined to provide a figure, and officials with both the county Planning Department and Haleakala Ranch said they either didn’t know or couldn’t provide the number (grading the road did require a $34,520 bond, which county civil engineer Lance Nakamura said represented just a fraction of the grading costs).

According to Starr, the road lies entirely on Haleakala Ranch land, which he said was the road’s main user. But he added that OW Ranch and Kamaole Ranch (which is owned by Winfrey’s former personal trainer Bob Greene, who is also listed as a manager for OW Ranch) retain access rights to the road that dated back to OW Ranch’s original purchase of the 1,000 Upcountry acres from Haleakala Ranch. Starr called the original dirt and gravel road “very rocky and dusty” as well as “dangerous,” which the grading permit and accompanying drainage report makes clear.

“We will paved [sic] approximately four miles of road 12 feet wide,” states the county drainage report. “Grades which is [sic] greater than 12 percent will be constructed out of concrete. We will construct drainage swales along the paved road, with plastic liner. All slopes will be graded at a 3:1 [ratio].”

Hugh Starr referred to the road as a “driveway” that “makes going in a lot easier,” though he added that the road doesn’t actually reach any dwellings owned by OW Ranch or Kamaole Ranch. “It was an existing ranch utility road,” he said. “The Department of Water Supply, Maui Electric and Haleakala Ranch all use it.”

Rumors about the road have flown about the island for months. During a Jan. 11 Maui Planning Commission hearing on OW Ranch’s request to extend a permit for its Silver Cloud bed and breakfast in Kula, Chairman Jonathan Starr (no relation to Hugh) asked OW Ranch agents whether the road existed and if it tied into Winfrey’s Silver Cloud bed and breakfast.

Tom Welch, an attorney representing OW Ranch, Kamaole Ranch and Silver Cloud, said the road did not connect to the Upcountry bed and breakfast.

“Mr. Chairman, yeah, in I think it was 2003 [sic] when Kamaole Ranch LLC, an affiliated entity, bought the land, bought [a] thousand acres from Haleakala Ranch in this area,” Welch said during the hearing, according to the official minutes (a receptionist at the Kahului law firm Mancini, Welch & Geiger said Welch was unavailable to comment for this story).

“They negotiated with Haleakala Ranch to get an easement over an existing ranch road so that, so that there could be access down below… [T]he way it’s set up, and the way it finally turned out was, the ranch granted an easement for the personal use of the particular client. And it’s over the ranch, it’s over an existing ranch road, and it allows them to, allows the client to use it from time to time subject to notice requirements.”

Curiously, at the hearing Welch also told the planning commissioners that “this is not a entire, entirely harmonious situation between the use of the ranch land for ranching purposes and the personal of use [sic] but it’s all worked out and that’s basically the situation.” When asked what Welch meant, J. Scott Meidell, an agent for the Haleakala Ranch, denied that any tension existed between Haleakala and OW Ranches. “There’s no disagreement over it at all,” he said.

Another curiosity: The original grading and grubbing permit application, dated June 22, 2010, indicated “OW Ranch LLC” was the property owner, with “Hugh Starr” listed as the agent. At some point that name was crossed out and the words “Haleakala Ranch Company” hand-written next to it. The new agent listed was Meidell.

“I don’t know why” the crossing out occurred, Meidell said. “But the actual landowner has to sign the permit, and Haleakala Ranch is the landowner.”

In any case, though the road is not visible from either Piilani Highway in Kihei or Haleakala Highway in Kula, Hugh Starr said members of the public still find their way to it.

It’s hard to monitor the road,” Starr said. “There’s some concern about the general public. It’s kind of a double-edged sword because the road is very attractive to skateboards and joggers. We have definite security issues.”

Illustration by Scrappers



  • Jeff Smultz

    Open the road Oprah you greedy liberal pig

  • Anonymous

    I can honestly say that I reread this and after doing so I have read more interesting stuff in meeting minutes from the city’s planning commission. If the article was to argue the public use of Oprah’s private property may I ask the writer one simple question? Would you allow for your neighbor to your right to cross through your garden and home to get to the home of the neighbor to your left just to save some time?

  • Anonymous

    Wow! Where is the author going with this article? Very informative if we readers really cared about the process of getting a private road made, however horrible if there was supposed to be a point.

  • BegFor.iT

    If you’re in a boat about 200 feet from shore in Kihei you can see it going up the hill. The sun reflects off of it nicely.

  • Jen Russo

    Thank you Erik!

  • Erik Blair

    Excellent article!