Backpackers aren’t born that way and it’s not an easy hobby for most people to stick with over time. But if you’ve caught the ‘backpacking bug’, it’s a passion that provides many challenges and rewards for the mind and body. Here’s my story of how I became an outdoors person and steered my life away from chasing money and professional titles to one that emphasized personal happiness and contentment. Everybody’s path is different but this is how I ended up where I am today.
To preface, I had always been a day hiker from my teens on, although casually. I did a little bit of backpacking in high school, and some camping in college and graduate school, but that was the extent of my outdoor recreation until I was in my late thirties. Everything changed after that when I developed a life, separate from my career.
It started with sea kayaking which I did for about 2 years before I switched over to whitewater kayaking. That was the sport that really made me an outdoor fanatic. At my apex, I was paddling 60 days annually, including winter, and driving over 10,000+ miles a year to river put-ins all over New England, including Canada.
I started as a river runner on class 2 rivers and worked my way up to class 4, dabbling a bit in playboating and creeking. I got good enough to become a leader for the Appalachian Mountain Club and an instructor on club courses.
Whitewater kayaking is a great sport that requires a lot of practice, skill, physical endurance, and safety training. When I was really into it, I’d paddle on both days of the weekend, and practice my combat rolls in a pond near my house every evening after work. My car stood out in the company parking lot because there was usually a kayak tied down on the roof.
There came a point, however, where my paddling friends became interested in running harder and harder class 4 and even class 5 rivers. I was more comfortable on class 3-4 water and stopped going kayaking as much since my friends didn’t want to run the easier rivers that I preferred.
Let’s Take a Walking Vacation
Right around then, my wife and I decided to do something different for our August summer vacation. Instead of heading to the Gunks, a mountain range located outside of New Paltz, NY famous for its hiking and rock climbing, we both agreed that we’d go on a guided hiking trip in the Shetland Islands off the northern coast of Scotland.
We decided on the Shetlands because we had had a great vacation a few years earlier on Orkney and because I knew of a great guide service called North-West Frontiers that offered a Shetland trip. I had been hiking with them about 10 years earlier, back when Andy Sherman owned the company, in a series of day hikes centered around Ullapool in the Scottish Highlands.
At the time, I was also fiddling (violin) quite a lot and looked forward to immersing myself in the local music. The Shetland Islands have a strong fiddling tradition and we were looking forward to sampling live music in the Shetland pubs since my wife and I enjoy live folk music.
The tour included 6 days of walking with 6-to-10 mile hikes each day. I was prepared for these distances, but my wife needed to get back into shape to complete these walks comfortably. So, every other morning, we’d take a hike before work in the Middlesex Fells, a nearby nature reserve.
Initially, we started walking an hour at a time: 30 minutes in and 30 minutes out. But over time, we graduated to longer and faster walks, as my wife’s endurance increased. These were easy hikes for me, but I started making them more difficult by carrying more weight in my backpack.
Doing these walks every other day required that we get up by 6:00 am and hike before work. Waking up early was fine with me, but it was a big lifestyle change for my wife. Still, she was willing to do it and these walks became something we both looked forward to.
I also enjoyed these hikes because I found them mentally and emotionally restorative. So much so, that I started hiking in the Fells by myself during our off days. Imagine being able to hike 5 or 6 miles every day, early in the morning. The woods were deserted at this time of day except for the birds and the trees. I’d arrive at work around 10:30 am, completely blissed out physically and emotionally with a post-hike buzz. I had a high-tech job so I could rearrange my schedule around the best commuting hours.
I’m never sure whether anyone else has the same emotional reaction to hiking as me, but I found that I could hold the insanity of work off at a distance after these morning hikes, rather than get emotionally drawn into it. I always feel this way after a backpacking trip where all of the trappings of the “civilized world” are stripped away. When I return home, work crises seem relatively unimportant and I’m able to remain unflappably aloof for a few days.
Summer rolled around and we were both ready for our Shetlands trip, but then the unthinkable happened. There was a terrorist incident at Heathrow Airport and British Airways canceled our flight from the US to London. This completely screwed our travel plans and we were forced to cancel our trip. Luckily, I had taken out travel insurance and we were able to get a refund for the bulk of our expenses.
After that, my wife stopped hiking with me every morning, but I was hooked. I started looking for other opportunities to hike and started to go on overnight backpacking trips with the Appalachian Mountain Club.
Although I lived in the Boston Area (at the time), I started hiking with the NY/NJ Chapter of the AMC which does a lot of hikes in the Catskills. This is an area adjacent to the Gunks, which I had day hiked extensively during several preceding summer vacations. I fell in with some kindred spirits who lead hikes for the NY/NJ chapter, hiking with them in New York, Connecticut, Vermont, and New Hampshire.
I also sampled some hikes with the local Boston AMC chapter but didn’t find leaders that I really clicked with. The size of the Boston-led day trips, felt immense, with 20 or more people attending the hikes. I didn’t enjoy hiking with this chapter and stopped signing up for trips with them.
That changed when I got involved with the Boston chapter’s Winter Hiking Program, which is a lot more hardcore. I soon became a 4-season hiking and backpacking leader for the AMC, although I always kept my trips small, never exceeding 6 participants.
There came a point where I was spending equal time backpacking and kayaking on the weekends, alternating activities just about every weekend. I realized that I couldn’t keep switching back and forth and that I had to commit myself to one sport or another.
The Long Trail
Around this time, I can remember a weekend kayaking trip on Maine’s Dead River where a paddling buddy of mine told me about his end-to-end hike of Vermont’s “The Long Trail.” I can still remember that trip vividly – we were staying at Webb’s Campground at The Forks and I was camping for the first time in a Hennessey Hammock. That was when the idea of hiking The Long Trail was first planted in my head.
After that summer, I stopped whitewater kayaking and dedicated myself to getting ready to backpack The Long Trail. My wife insisted that I spend a year preparing by going on a lot of backpacking trips, which I did.
After a year of preparation, the rest is history. I section hiked The Long Trail in 2008 (before I started working for myself) and remain a hiking and backpacking fiend to this day. Since then I’ve section hiked about 1400 miles of the Appalachian Trail, backpacked coast to coast across Scotland twice, and I’ve hiked and backpacked over 7000 miles throughout the White Mountains in New Hampshire and Southern Maine, where I now live. I love the White Mountains, which I now call home.
And that is the story of how I got into backpacking.