Timothy O’Brien: Trailwalker

Timothy O’Brien: Trailwalker

Questions & Answers with community faces

Timothy O’Brien (55) graduated from Benzie Central High School in 1983. He has worked retail in Benzie County since 1989; he worked at Nugent Hardware in Benzonia for 12 years, and he has been at Crystal Gardens of Frankfort since 2003. For the past four years, O’Brien has been in the Rock Shop at Crystal Gardens. 

That is where the editor of this newspaper actually first met O’Brien nearly two years ago, when she was buying a new-to-her, used Canon camera and lens that O’Brien had listed for sale on Facebook. He explained that he had begun selling possessions to help pay for a long upcoming trip: O’Brien had planned to hike the Appalachian Trail—all 2,190 miles of it—beginning in March 2020. 

But, as we are all too aware, 2020 had other plans. 

Not to be discouraged, however, O’Brien has made two attempts to this journey: the original began on March 11, 2020—though that trip ended less than a month later—and again on March 3, 2021. 

Twice now, O’Brien has spent months training physically for this trip; he could often be seen walking around the Frankfort area with a 20-pound pack on his back. This time, it seems like O’Brien will make it—he is currently around 1,800 miles into the trek, with less than 400 miles left to go. 

O’Brien has recently been interviewed from the trail by local television channels, and although this is a little different than our typical interview series on impactful Benzie County characters, The Betsie Current felt it was important to catch up with O’Brien by phone in New Hampshire, as he gets close to finishing what has been a years-in-the-making journey.

The Betsie Current: When did you first get interested in hiking? What got you interested? 

Timothy O’Brien: Well, probably just being a kid that was raised in the 1970s; my folks were into camping. I think I got introduced to it by them. It was kind of a renaissance period back then for finding ways to get into nature. I’ve always been interested in the outdoors. As far as this particular trip, I think I saw a National Geographic special on the Appalachian Trail that just happened to pop up in my Netflix queue, maybe about eight years ago. It was an “I’m gonna do that someday” thing. Lots of people say that they want to do something like this, but not a lot actually do it. I got to the point where I was like, “No, I need to actually do this.” But this is really my first big trip like this; I mean, I hadn’t done any overnight backpacking until I decided that I was gonna do this. I did shake-downs to prepare for this; a couple-hundred-mile stretches on the North Country Trail—the longest in the National Trails System, which stretches 4,700 miles across eight states, and a lot of it goes through Michigan. I didn’t really have any experience with long-distance hiking before that. 

Current:  Why did you decide to take on this specific trip? And why do it solo?

O’Brien: The Appalachian Trail is, like, The Pilgrimage. It’s just what people do: most people out West will hike the Pacific Crest Trail, instead, but most people in this part of the country [the Midwest and Eastern United States] do the Appalachian Trail, because it’s closer to get to, relatively speaking. Of all the scenic trails, it’s probably the hardest one to complete. But more than that, it is America, what America’s about. It goes through 13 states; starts in the south, ends in the north. It’s rural America. It’s so much more than just the trail; it’s the people along the way, the Main Street towns that are along the way. It’s one of those things that I’ve always wanted to do, to see. As far as doing it solo, I actually did start with a friend this year. But the thing about hiking this trail is that everybody hikes at their own pace, and it’s very difficult to hike with other people. If you don’t want to do 20 miles today, let’s say you want to do 14, but the group wants to do 20, then you’re just sort of stuck doing what you don’t want to do. I chose not to be in a “tramily,” a trail family, because it gets too complex. It makes things more difficult. “Hike your own hike” is the big saying out here, “HYOH,” and part of that is you have to do what you want to do, not what someone else wants to do. I’m not lonely out here; I talk to people I meet. You’re never really alone out here. I just saw someone today who I haven’t seen since Georgia. And I’m not really scared of anything; some people are scared to camp alone. I enjoy the solitude. I have been hiking some of it with someone, on and off for about 700 miles of it, and as I get closer to the finish, I might try to meet back up with him; it might be nice to finish with someone, to go through that together. 

Current: What does a typical day look like for you right now?

O’Brien: I wake up at probably quarter to 5 right now. I pack pretty quickly now that I’ve been doing it for a while. I don’t eat breakfast right away, so I usually start hiking around 5:15 or 5:30. I hike a few miles, eat a snack, brush my teeth, go to the bathroom usually. Depending on my pace, I’m usually done at 4 or 5 at night. I’ve been doing 20 to 28 miles per day lately; my biggest day was 32 miles. I snack during the day—I don’t stop to make a formal lunch, I just graze as I’m hiking. When I get done for the day, the first thing is to set up my tent, eat dinner. I’m usually asleep at 8. I look at it as work that I have to do each day. I’d rather get the work done quickly, and then have the rest of the day to do what I want, to relax. Some people sleep in out here on the trail, and I just feel like that’s such a waste of the best part of the day. 

Current: How did your plan for this trip change when the COVID-19 pandemic hit the United States?

O’Brien: That was pretty weird. So, I started last year on March 11 [of 2020]. Just before everything got crazy. And I initially asked the people from the Appalachian Trail Conservancy what they thought. And they said that they thought it was gonna be the same as the year before; that they’d have just as many people hiking as in 2019. Then, it changed a bit, and became, “Well, if you’re already on the trail, go ahead and finish, but we don’t want anyone new to start it.” Then, it changed again; round March 23, they put out a bulletin that you should get off trail immediately. Initially, people said I was in the safest place in the world—being on the trail, no people. But it was scary as hell, because if I got hurt, where would I go? What would I do? It was such a weird thing to have to quit last year, but I think I did the right thing. Then this year, it was kinda like, “Well, I gotta live my life. I’m gonna do this again.” I think everyone was fed up with COVID stuff at that point, and I felt like I wasn’t doing anything that was taking any more risks than I would have been at home, so I felt like it was the right thing to start again, on March 3 [of 2021]. If I hadn’t started last year and had to quit, I don’t know if I would have done it this year, though. But because I had had to quit last year, it was like, I wanted to be able to finish what I’d started, and I was anxious to get out there. But things really worked out good for me, in being able to do it this year instead of last year: I was able to save twice as much money, the weather has been awesome this year. And I hiked 134 miles of it last year, a good shakedown, to sort of prepare. All in all, it was a very hard pill to swallow when I had to quit last year, but it’s all good now, and I think I prefer the way that it worked out. 

Current: What are some of your favorite places that you have been so far? Top three memorable moments? Anything scary or unsettling happen?

O’Brien: Top three would have to be Roan Highlands in Tennessee; Grayson Highlands in Virginia; and gosh, there are so many places that have been beautiful. Probably the Smokies in Tennessee—those were beautiful, even though the weather was crappy for half of it. But when the weather got nice, it was just beautiful. Everyone has been asking what my favorite spot was, but it’s so hard, because I could list 20 places; it’s hard to pick one or two. And they tell me that I haven’t even gotten to the prettiest part, people say, which is coming up. As far as memorable moments: it’s funny, the things you remember. I’ve had a few equipment failures. My air mattress leaked the first night, so I had to sleep the first four nights with no air mattress in 20-degree temperatures. There were some storms that I had to go through; one where water was up to my knees, with thunder and lightning, and I could barely see the trail. Nothing that’s really scared me, but definitely memorable. I’ve had other equipment failures, like the pack that I started with ripped, so I had to get a new pack, which is a little heavier. I’ve got a GPS watch that just died on me; I just bought a new one yesterday. I’m on my fifth pair of shoes. Just small stuff; I’ve lost a few things, like my spoon the other day, which was no fun. There is a point where it feels like everything is falling apart, like the wheels are falling off the bus. I’ve had this feeling for the past week or so: the closer I get to the finish, the more I want to be done, but part of me says, “Slow down, enjoy it,” while the other part is like, “Man, just finish it up.” Other through-hikers feel the same way. It’s a bittersweet feeling, because this is supposed to be the best part of the trail, the prettiest part. But the point that defines my whole trip was when I had shin splints, and I thought it was the end of my trip, I thought I wasn’t going to be able to keep going. But I was able to overcome that, and after that, I just felt unstoppable. I look back and, for some reason, overcoming that has been the part of this trip that I like the best. 

Current: How has this journey changed you? How do you hope that you will continue to grow? What is next? 

O’Brien: Oh boy, man, well, I’ve always lived a pretty simple life. This is not much different than that. The feeling of accomplishment is going to be amazing. What’s next? I actually would like to go on a hiking trip with my son. Kind of connect with him. He actually called me the other day, and he asked me that. I don’t think I want to do another hike that is this long of a distance—it’s a once-in-a-lifetime thing for me. It’s such commitment, just the logistics of it all, and I don’t think I could pull it off again. But maybe a month-long trip, that would be nice. 

Current: Back in Benzie County, what kinds of things do you do for fun? What other things are you involved with? What are your favorite local events and activities? Any favorite dining, recreation, hiking spots?

O’Brien: I like to go rock hunting. Hanging out with friends—sounds like something a high school kid would say, but it’s true. Photography. I used to enjoy the Elberta Solstice Festival; that was always my favorite, but they don’t do it anymore. I wish there were more summer activities like that, for locals. I really enjoy going to Stormcloud, Fusion, Cabbage Shed. The Frankfort and Elberta beaches are hard to beat; Point Betsie. I like the dunes trail in Elberta. That boardwalk down in Arcadia is awesome; that’s probably one of my favorite places now. 

Current: How have you seen Benzie County/Northern Michigan change since you grew up here? What are your hopes for the area in the future? What could Northern Michigan do to attract more talented young people to this area? What else does Northern Michigan/Benzie County need?

O’Brien: Boy, it has changed a lot. I’ve been in Benzie County since 1975. It’s kind of like everything in the area has changed, though, so I don’t know if Benzie County is any different than the rest of Northern Michigan. For instance, I grew up out by Lake Ann, near where Mistwood Golf Course is now, and that was just cow pasture then. Now you see golf courses. Part of me is like, “It’s sad,” but part of me knows that the economy has to grow, that people need jobs and things to do. I don’t mind the direction it’s going; the people who live here need to make a living. It’s a fine balance. Look at Crystal Mountain; it just used to be just a ski resort, and most places that were just ski resorts didn’t make it. But they made it into something that is year-round, and it survived, and now it’s thriving and employs all those people. And I think that’s what Benzie County needs: to figure out how to make things more year round. As far as what do we need here: affordable housing is always on top of everyone’s list. It’s so hard to find a place to live, especially when you’re young. I struggle with that, and I’m 55. 

Current: What are the biggest challenges and rewards of living/working in Benzie County and in Northern Michigan, in general? What is the best or most rewarding part of your job?

O’Brien: To make a decent wage and afford to live here is the biggest challenge. But I say that I get to live here and do what I like to do, whereas I see people who feel like they have to work 50 weeks of the year at a job they don’t like so that they get two weeks of heaven when they visit here. It’s that old saying, “View of the bay is half the pay.” But it’s true. Other rewards are that I really enjoy working with the public; I really like working retail. Now I’m making jewelry, and it’s very rewarding to have people look at something I made and want it and appreciate it. I can consider myself an artist now. Which is weird. In school, I couldn’t draw a stick figure. I was in band, not art, for a reason. Now I’m an artist, and I’ve got people from all over the country who buy stuff from me and are excited to buy stuff from me, which is cool. And all of the people who seek me out for help; even when I was at the hardware store, I was the go-to guy to solve people’s problems, which is pretty satisfying. 

Current:  What is the first thing that you plan to do when you get home?

O’Brien: I will tell you this, one of the main reasons that people get off the trail isn’t because they’re hurt, it’s because they’re homesick. I’m not homesick, I wouldn’t say that, but I do miss my friends. I want to hang out with my friends and just relax, not feel like I have something that I need to do each day. I will have to get back to work pretty quickly, though, not much time off. But I am looking forward to sleeping in and relaxing. I took a “zero” yesterday, meaning that I didn’t hike and did a rest day instead, and it was such a hard thing to do, not to feel like, “Man I gotta get out and hike these miles.” It’ll be nice to wake up in the morning and not have to go anywhere. To be able to see my friends. It’s funny, because I moved away [from Benzie] a couple of times, and you live in a small town, and you think, “It sucks, everyone knows my business.” But then there’s the other side of it: it’s nice to go to the gas station and have whoever is working say, “Hi, Tim.” The small things like that, that you take for granted. I ultimately do like small-town life. It’ll be nice to see everybody. Catch up. It’s so weird out here. Like, I don’t know what’s going on in the world right now. Going back to one of the most challenging things: I’ve been through 12 states. I’m at 13 now. And I hate to talk about COVID, bring it back to that, but every state that I get to, they’re dealing with it differently. I’m in New Hampshire right now, where some of the places you have to wear a mask when you get in. But some states along the way, you didn’t see a mask at all, nobody was wearing them. Then, some states, everybody—even on the street—was wearing one. And I’m not trying to be a rebel right now. I just don’t know, because each state is doing it differently. The other day, I got on a bus to go into a town, and the bus driver gave me the dirtiest look in the world, because I didn’t have my mask on at first. “Sorry, dude, I didn’t know what it was like here.” Part of it is that I kind of don’t want to know about what’s going on in the rest of the world, in the real world. Like, most days, I don’t know what day of the week it is; until it’s a day when there are lots of day hikers, it’s Saturday. I’ll catch up on the world and current events soon enough. But what I am hoping is that things are almost normal when I get home. I don’t know if they are or not. That’s been my little fantasy—that I can go down to Stormcloud and have a beer with a friend and not have to wear a mask. I don’t know if that’s gonna happen or not, but that would be kinda neat. 

Timothy O’Brien started the Appalachian Trail on March 3, 2021 in Springer Mountain, Georgia. He expects to finish around July 15 or 20—which is about three weeks ahead of what he initially anticipated, as he has been going faster than he expected—ending at Mount Katahdin, Maine. He is carrying about 20 pounds on his back, enough for four days of food and water.

Featured Photo Caption: Five years ago, Timothy O’Brien suffered a heart attack that almost killed him. Two years ago, he started preparing to hike the 2,190-mile Appalachian Trail. But last March, he only made it 134 miles before the COVID-19 pandemic got in the way of his plans. Not to be discouraged, O’Brien kept training and re-entered the trail in Georgia on March 3, 2021. As of print time, he is closing in on 1,800 miles, with less than 400 miles left to go from the finish line in Maine. O’Brien is on his second backpack, second GPS watch, fifth pair of shoes, and he is down about 35 pounds from when he started. Photo courtesy of Timothy O’Brien.

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Aubrey Parker

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