It happened on southbound Highway 85 before De Anza Boulevard just after 7 a.m.
The pilot is OK and walked out without a scratch after being able to land his plane in the opposite direction of traffic.
The landing caused a traffic nightmare for drivers in the Cupertino area, with lane closures ongoing and extending over four hours.
"I started to lose my engine, made a mayday call into the Palo Alto airport, my destination," the pilot Peterson Conway said.
Conway commutes from a farm in Carmel to Palo Alto every other day but on Monday morning, something went terribly wrong.
"I left my farm in Carmel at 6 a.m. this morning, called the airport and asked them to top me off, we don't know what happened, if that did happen or it didn't but clearly I had an engine out," Conway said.
Conway says airport officials originally tried to divert him to San Jose, but he said when things became clear he wasn't going to make that, he aimed for the nearest football fields.
"I then, saw kids out in the football field I was trying to make and I couldn't make that," he said. "Northbound traffic on 85 was back-to-back and nobody would be able to see me coming down on top of them so I opted to land on the southbound lane."
He made that landing just around 7:15 a.m. Monday on Southbound Highway 85 just before De Anza Boulevard.
"I turned on all of my lights, the cars started to separate, there were a couple of high-speed Porsche SUV's heading my way playing chicken and I was rocking my wings to try and get everyone's attention and I had to put it down," Conway said.
Neighbors stood at a nearby overpass for hours watching the process unfold.
"It was a miracle that he didn't hit any oncoming traffic since he landed into oncoming traffic," said Gordon McIver from Palo Alto who was watching.
Though grateful that there were no serious injuries, Conway said he's sorry for the impact on the community.
"I just feel horrible to everybody in their morning commute and all the first responders here," he said.
While the pilot is safe, the miraculous landing disrupted traffic and caused a ripple effect.
Just as ABC7's crew was preparing to interview a CHP spokesperson on scene of the crash, two pick-up trucks slammed into each other, causing one to slide into the closure, scraping a CHP patrol car.
Luckily, no one was seriously hurt, but traffic was reduced even more to just the far left lane open on southbound Highway 85.
Crews worked to remove the wings of the plane first before towing it to the Palo Alto airport.
All southbound lanes of state Highway 85 in Cupertino reopened at about 1:20 p.m.