Justin and Moondog’s Skate Adventure: Boarders set record by skating entire length of Natchez Trace

Published 12:39 pm Monday, October 16, 2023

NATCHEZ – Justin Bright and David “Moondog” Roop didn’t know anything about Natchez until they arrived unceremoniously at the Natchez Trace Terminus on Sunday.

After completing a 444-long skateboard journey along the Natchez Trace, the pair arrived at the oldest settlement on the Mississippi River and headed first to a laundromat, then to get food.

But as they followed their GPS guidance into town and to their hotel, they were enthralled by the architecture and the history of Natchez.

Email newsletter signup

“I’d never really heard of it,” said Bright, a 25-year-old journalist-turned-conservationist and avid skater.

After discovering “a gauntlet of historical signs,” they soon began soaking up the history and the hospitality that makes Natchez such a popular destination – a welcome surprise after completing their record-setting thru-skate.

The duo started their longboard skate on Oct. 3 at the start of the Natchez Trace in Nashville, Tenn.

“The first few days were slower, but then we got into the pace of 40 to 50 miles per day,” Bright said, explaining that the beauty of their approach to travel allows them to “stop and chat with people.”

Roop and Bright are avid skateboarders, hikers and outdoors enthusiasts. The pair met while both were skating the length of Florida – independently – and they skated across New Mexico together. They’ve skated several trails together and separately, and once someone suggested they consider the Natchez Trace, the idea just clicked. They tentatively set a date and began working toward the adventure.

“I wanted to do it in September,” Roop joked, “but he said no.”

“That’s because if the weather on the Trace was anything like it is in Florida in September …” Bright added, joking about the exhausting heat and humidity of the South.

As they traveled the Trace, the duo saw first-hand the effects of the drought on Tennessee and Mississippi. “We’d pass creeks that just weren’t there,” Roop said.

They camped wherever they could, carrying their tents, food, water and supplies on backpacks as they skated. “Dirtbags on skateboards,” Roop said, describing the pair. “But dirtbag is a good thing.”

And they took time to experience the journey.

“We met this guy, Andy, who was a farmer,” Roop said. “He literally stopped in the middle of the street to ask us about skating.”

They talked for 20 minutes about boards, wheels and the journey. “Then he said, ‘Y’all want some sandwiches?’

“We ended up going to his house and spending the afternoon there. It turns out his wife’s family arrived on the Mayflower, and his family came to Jamestown …”

“It’s amazing how saying yes or no to things could change the direction of your life,” Bright said. “We could’ve said ‘no, we’ve got peanut butter and tortillas’ and skated down the road.”

By completing the journey, the pair become the first people to skate the entire length of a National Scenic Trail. “There are only 11 of them,” Roop said. “Of course, this is the only one that is fully paved.”

And they’ve set a benchmark that they hope might encourage others to consider distance skateboarding, either competitively or as a hobby.

“This type of skating – distance skateboarding – is the most sport-like of them all,” Bright said, explaining how it compares to other styles of skateboarding. And yes, it is a sport.

“There’s the ultraskate,” Bright said, referring to the Homestead Miami Ultraskate competition, which takes place on a Nascar speedway. “It’s a 24-hour race on a skateboard … and you can skate as much or as little as you like. The first time I went, I was there as a reporter covering it. I left thinking, ‘I have to do this’.”

And he has – three times.

So now, Bright and “Moondog” share the mission of promoting the benefits of distance skateboarding, setting records and exploring the country – one road at a time.