Peaks Islanders Leah Day and her son, Oakley Bradenday, stop for a photo on the Missouri border during their 4,400-mile, coast-to-coast biking adventure. Courtesy photo

PORTLAND — Leah Day wanted to do something big when she turned 50. That something turned out to be biking the entirety of the Transamercia Bike Trail,  a more than 4,400-mile trail stretching from Astoria, Oregon, to Yorktown, Virginia, with her 16-year-old son.

“I’ve always wanted to do something like this,” said Day, who started the quest Aug. 1 and ended it 84 days later on Oct. 24. “Biking has a really good pace to see things as you go. Each state you cross into has its own really distinctive personality.”

Day and her son, Oakley Bradenday, a freshman at Casco Bay High School, will discuss their adventures Thursday, Nov. 14, from 6:15 to 7:15 p.m., at the Peaks Island Community Center.

Leah Day and her son spent three months traveling the Transamerica Bike Trail, which stretches from Oregon to Virginia.

The trail, founded in the 1970s in advance of the country’s bicentennial, follows rural roads through 10 states, passing Yellowstone and Grand Teton national parks in Wyoming and on through the mountains of Colorado and the flatlands of Kansas. It crosses the Mississippi River and Appalachian ranges before coming to an end at Chesapeake Bay.

While the trip was a scenic way to see the United States, Day and Bradenday said it did not come without its challenges, like the threat of bears by Yellowstone, fierce headwinds in Kansas and wild dogs in Kentucky, not to mention sharing the road with 18-wheelers and other big vehicles.

Friday, Sept. 13, was a memorable day for him, Bradenday said, because of a close call. While trying to get out of the way of a large truck on a busy stretch of road, he accidentally rammed into his mother’s bicycle when she stopped to let the vehicle pass.


“Almost everyday there was a different challenge,” he said.

Day is writing a parenting book about their experience, how it brought her closer to her son and how to make the most of challenges.

“It was incredible. One of the biggest things we learned was you have so much more strength than you thought you did,” she said.

Their course was outlined through 144 small maps that could be attached their bikes, with recommendations of where to eat and stay every 50 to 75 miles or so.

Most of the nights, Day said, they camped in public parks and stopped at local gas stations for food. She  said she and Bradenday would not have been able to get through the trip without the help from friendly people they met along the way.

“The people were wonderful,” she said.

Bradenday said his favorite day on the journey was when they were in Saratoga, a small town in Wyoming where he met up with some teenagers his age and went ATV riding.

Day already wants to do the trip again.

“I would like to do it every five years. I am trying to find a job where I have summers off, because it is really important to have these experiences to get out of the routine of everyday life,” she said. “There need to be more vision quests like this in our lives where you just put yourself out there and explore.”

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