BATON ROUGE, La. (BRPROUD) — The Natchez Trace Parkway is a 444-mile recreational road winding through Tennessee and Mississippi. Two men are trying to become the first to tackle the trail on skateboard, and one plans to extend his journey, ending in Baton Rouge.

“We are skating for a cause. ‘Cause we’re awesome,” Roop joked.

Adventure enthusiasts David “Moondog and Justin Bright started on Tuesday, Oct. 3, on their skateboards and have traveled daily since. Roop said it’s called thru-skating, which “is essentially long-distance hiking on a skateboard.” He’s a hiker, and most people know him by his nickname.

The pair only gets off the road to check out a local restaurant, recharge their electronics, resupply for the journey or sleep. They carry tents, food and water.

“In the hiking world we are known as ‘hiker trash,” Roop said, “basically meaning we will sleep anywhere, eat the most unhealthy food and drink the sketchiest water. It’s a title that is earned and worn with pride.”

The Natchez Trace is about 444 miles long and ends at Natchez, Mississippi. Roop said the original goal for the duo was to be the first people to skate the parkway and finish in Baton Rouge.

“We are really just doing this to have fun and because it hadn’t been done,” Roop said. “Someone mentioned this trail to us, and within hours we had decided to do it. That was pretty much our planning phase. We had the skillsets needed from prior trips that we can show up to (a) trail already pretty prepared. We like to think of ourselves as adventurous types, and this was our next grand adventure.”

While on the ride, Bright decided he will likely end his journey after the Natchez Trace Parkway to meet a prior commitment.

Roop plans to continue to Baton Rouge. Someone told him Baton Rouge “was filled with interesting people, history and beautiful nature.”

Why make this journey on skateboards?

“Skating is definitely our favorite form of travel. Have you ever seen someone frowning on a skateboard? Me neither,” he said. “It allows us to choose more adventures as we can go further if we’d like to or slow down if we want to. We can spend our time more on experiences than just on making miles.”

The two met when they were individually skateboarding 1,100 miles across Florida. The duo then went to New Mexico, where Roop lives, and skateboarded together around the state for just under 500 miles.

Roop said their gear is built for long trips and rough treatment. He is using a “Pantheon Quest longboard with the new Pantheon Karma wheels,” and Justin has “a board by Underground Longboards with Oragatang Caguama wheels.”

“If something happened we would work together to figure out what to do. Part of the adventure is having to figure out solutions when something goes wrong,” he said.

At their current pace, Roop believes they will finish the Natchez Trace Parkway on Tuesday, Oct. 17. Roop is aiming to make it to Baton Rouge by Saturday, Oct. 21. He looks forward to checking out The Red Stick.

The duo is trying to cover 30 to 50 miles a day on their boards, subject to road and weather conditions.

“We are pretty good at endurance but pretty bad about goofing off, which is kind of the point,” he said.