Forty years after he first climbed Mt. Katahdin, the highest mountain in Maine that marks the northern terminus of the Appalachian Trail, Bruce Matson is going back – and he’s hiking the full length of the trail to get there.

The chief legal officer and partner of downtown law firm LeClairRyan leaves this weekend for the nearly 2,200-mile trek, taking on Saturday the first of what’s said to be the 5 million steps that the full trail requires from its southernmost endpoint in Georgia to Maine.

Matson’s wife Cheryl will accompany him that first day; then, starting Sunday, it’s the rest of the way solo for what Matson expects to be a five-month hike, with only his backpack and supplies and his thoughts to keep him company between camping points and interactions with fellow hikers on the trail.

For Matson, who just turned 60, the full-trail “thru-hike” fulfills a lifelong dream and goal of returning to Mt. Katahdin, which the Connecticut native first climbed as a camp guide in the late 1970s.

“It will be a huge sense of accomplishment. I think it’s going to be the hardest thing I’ve ever done,” said Matson, who recently returned to hiking after years of what he described as putting his work and family first.

The William & Mary alum has been preparing for the hike for months, plotting out his journey through the 14 states the trail traverses while documenting his efforts on a website and podcast, which also have promoted the charity behind his trek.

In addition to fulfilling his personal goal, the hike is giving Matson a way to give back, as he’s aiming to raise $250,000 for the Appalachian Trail Conservancy through a funding challenge, aptly named “Return to Katahdin.” Matson kicked off the challenge with a $100,000 matching fund contribution, and the conservancy has established a crowdfunding page that as of Thursday had raised nearly $4,400.

LeClairRyan held a send-off party for employees and friends to raise funds for the challenge, with tickets going for $150 apiece. (A similar fundraiser was held over the weekend at Independence Golf Club.) And the firm is also using the hike as a way to promote healthy living among its staff, who will track Matson’s progress using pins on a map.

Matson said he’s aiming to hike a pace of 15 miles a day on average, taking every 10th day off to rest. While he’s hiked sections of the trail before, this is his first attempt at a full thru-hike, the term for completing a long-distance trail end-to-end.

“To me, the biggest thing is going to be, after two or three weeks, ‘Okay, this is cool, but I’m going to do this for four more months?’ And it’s dirty, difficult, wet, smelly, the same food,” Matson acknowledged.

“I’m as excited as I can be, I don’t expect to be bored or unhappy or thinking about quitting, but I’ve never done anything like this,” he said. “But I’ve tried to be realistic as opposed to just thinking about all the highs and not anticipating some lows.”

After winding his way through the Carolinas, Matson said he expects to reach Virginia by early April, noting the state accounts for about a quarter of the trail. He’s shooting to cross the Potomac River via Harpers Ferry in early May, and his projections put him in New York in June.

While he’ll be hiking solo, Matson said he won’t ever be solitary for long due to the trail’s popularity. According to the conservancy, the trail attracts 3 million visitors each year.

“I’ll enjoy having the social aspect of it. That said, I actually am looking forward to the solitude as well.”

Matson said that experience of being one with nature is what draws him to hiking –what drew him back to it even after decades without it.

“To be in nature, to have a sense of awe, I think, is still critical to life,” Matson said. “I think sometimes we take so much for granted – the speed of technology, the fact that I can take a photograph of this room and I could email it to a friend in Australia. To me, I think it’s great to be reminded about how amazing the world can be, and I think being out in creation is exhilarating, because of that sense of awe.”

Matson’s gear: Osprey Atmos AG backpack, Big Agnes Copper Spur UL2 tent, Mountain Hardwear Phantom 15 sleeping bag, Sea-To-Summit Reactor polyester liner, Big Agnes Third Degree sleeping pad, MSR Reactor stove, Sawyer Squeeze water filter and Black Diamond Alpine Cork trekking poles. Cup, knife and spoon, MSR trowel, REI Lightweight Alpine Gaiters and Electronics. Base weight: about 21 pounds Food and water: oatmeal, granola, gorp, tortillas, proteins (tuna, salmon, peanut butter), freeze-dried dinners. Total weight w/ food and gear: 31 pounds

This is the latest entry in our Downtime series, which focuses on business people’s pursuits outside the office. If you, a coworker or someone you know around town has an exciting or unique way of passing time off the clock, drop us a line at [email protected]. For previous Downtime stories from our ongoing series, click here.