
WILLIAMSBURG — Williamsburg resident Aaron Astray is currently in Texas with a 40-pound backpack and a skateboard, headed towards San Diego.
The 27-year-old originally set out on his trek for one last adventure before moving out, but according to Astray, it’s turned into much more than that.
“This journey has really exceeded my expectations in every aspect. All the interactions with the people I’ve met along the way have been amazing. That’s the most outstanding thing about all of this, I’ve just met so many awesome people along the way. They have been super happy and everyone just wishes me well along the way. I didn’t think I’d be meeting so many people,” Astray said.
Originally setting out for adventure, Astray quickly realized his trip had become important for his mental health.
“It’s definitely a trip that I wanted to do for myself, but the more I go along, it’s pretty eye-opening how being active and going out is good for your mental health. I’m not going out of my way to spread a message and promote what I’m doing, but the mental health portion is definitely an aspect to it,” Astray said.
In addition to the importance of taking care of his mental health, Astray has also become aware of the true amount of strength that he has.
“I have really learned that I can do a lot more than I expected and I’m very resourceful. I’ve impressed myself with the fact that I’ve managed to get this far and it just proves that you can do anything that you put your mind to. The hardest part is starting, so once you start, you can do anything you want,” Astray said.
With just his skateboard and backpack in tow, Astray frequently stops in small towns across the country to do laundry and take in the locals. He said that along the way, he’s attended festivals, concerts, and enjoyed even the smallest of towns.
“One place that really just sticks out for me is Oxford, North Carolina. It was a town where I was sitting there waiting for a package to come in the mail and I ended up being in that town for about a week. It was really cool. It’s a pretty small town, I got to meet a bunch of the locals, and there happened to be a hot sauce festival while I was there waiting for my package. I really liked the vibe they had there,” Astray recalls.
Astray is capturing his journey across TikTok, YouTube and Instagram. He travels between 20 and 40 miles a day via his skateboard. With a trip like this planned, Astray set out having done no physical preparations, something he says now that he is paying for.
“In my very first week, I had really bad ankle pain. I had a bad ankle for a good week and a half. I talked to one of my buddies who is a physical therapist and he told me to get a specific kind of brace, and other than that, that has been my only injury. The first three weeks were pretty rough with that, but I’ve been sore every single day,” Astray shared.
Astray dipped his toes in the Atlantic Ocean about 135 days ago before his cross-country trek began. He says that once he arrives in San Diego, he’s going to jump into the Pacific Ocean to celebrate.
“I’m sure it’s going to be overwhelming when I make that jump. I’m going to be so proud of myself for finally making it. I’m probably just going to cry tears of joy as I run across the beach,” Astray said.
As he enters the next phase of his trip, Astray hopes to send a positive message to those who view his channels.
“If you have something you really want to do, you just have to plan it out and commit. That’s the best advice I can give. If you really want to do something, the hardest part is the first step and that comes with planning and actually putting it into action,” Astray said.
He plans to finish his trek in the spring after being on the road for over 200 days.
To learn more, follow Astray on TikTok, YouTube and Instagram.

