The sky over the Lebanon Airport was dotted with small planes Saturday. In one hanger a 1942 World War II trainer plane prepared for take off.

The pilot, Gareth Williams, was 800 miles into a 3200 mile journey from Pennsylvania to California. In the cockpit, a picture of his son, Timmy, reminded him of his mission to help parents and families cope with a loss he has been all too familiar with.

"His picture goes with me everywhere," said Williams. "Timmy passed away February 2008. He was 11, just a week short of his 12th birthday."

A few years ago Williams came up with an idea to take other parents on a flight that could help put their minds at ease.

"The experience of flying in the open cockpit is peaceful, freeing, resting," said Williams. 

While the program has only been in operation for three weeks, Williams' uplifting rides have been quickly becoming popular with parents like Tammy Allen.

"My son passed away in February 2014," Allen said. 

Her son, Dakota, was a thrill seeker and avid traveler.

"The one thing he did not get to do was ride in a plane like the Red Baron so when I saw that plane, there was no question I had to finish that list for him," Allen said.

With each take off, grief can turn to comfort.

"You feel the wind through your hair, you have this unobstructed view and then when you look, this peaceful feeling comes over you," explained Allen. 

Timmy's "dream big" legacy will help other grieving family's know they're not alone, and it couldn't be more clear than from hundreds of feet in the air.

"In my mind I was looking at what my son sees every day, it was beautiful," Allen said.

Williams has planned to be in middle Tennessee another week before heading to Memphis and continuing his journey west.

For anyone interested in flying, a "request to fly" can be submitted by clicking here.