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How I Got into Backpacking

View from My Greylock

Last week, one of my regular section hiker readers asked me to write a post explaining how I got back into backpacking after a 20 year hiatus.

My wife blames herself for this one.

To preface, I had always been 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 about 20,000 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 do become a co-leader for the Appalachian Mountain Club and an assistant instructor for the Boston chapter’s Class 3 intermediate whitewater course, a grueling 2 day class taught on the Dead and East Kennebec Rivers in Maine.

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 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 (in addition to my bumperstickers.)

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 most 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. That was about 4 years ago.

The Shetland Islands
The Shetland Islands

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 it’s 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 6 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.

The tour itself was a week long, with 6 days of walking and 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 natural reserve located just 5 minutes from our house.

Middlesex Fells
Middlesex Fells

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 6am 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 too.

One thing that we both came to enjoy, somewhat unexpectedly, were our morning chats. With our busy professional lives, we had stopped spending a lot of time talking to one another. We rediscovered the art of conversation during our hikes and came to look forward to our walks because they let us talk to one another for long periods of time.

I also enjoyed these hikes because I found them mentally and emotionally restoring. 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 are 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’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 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. The Buddhists call it equanimity.

Summer rolled around and we were both ready for our Shetlands trip, but then the unthinkable happened. There was a terrorist incident at Heathrow 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.

View from West Kill, Catskills
View from West Kill, Catskills

Although I live in the Boston Area, 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’s changed since I’ve gotten involved with the chapter’s Winter Hiking Program in the past year, which is a lot more hardcore.)

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.

Border of US and Canada, The Long Trail
Border of US and Canada, The Long Trail

Around this time, I can remember a weekend kayaking trip on the Dead River where a paddling buddy of mine told me about his end-to-end hike of 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 to hike the LT by going on a lot of backpacking trips, which I did. It was during this period that I got heavily into lightweight packing and ultralight techniques.

After a year of preparation, the rest is history. I section hiked the Long Trail in 2008 and remain a hiking and backpacking fiend to this day. This year, I finished the Appalachian Trail in Massachusetts and Vermont, and all but 5 miles in New Hampshire. Next year, I’m planning to hike across Scotland in the TGO Challenge and I expect to finish the remaining White Mountain 4,000 footers on my list. After that, I’d like to find another long distance trail to section hike in New England, but haven’t decided which one to do yet.

And that is the story of how I got into backpacking.


  1. I was trying to guess how you possibly fit backpacking in while spending so much time making endless posts. After reading this, it's clear to me you DO NOT HAVE KIDS!

  2. I did the Highland & Hebrides tour with North-West Frontiers in 2006. Our guide, Iain Throw was very knowledgeable about history, culture, music & geology of the area. Had a great time and I’m looking forward to going back again.

    Peter Grealish

    New Engalnd Hiking Meetup

  3. Great story! Makes me think a little about how I got into hiking, and also about the sports and hobbies that I've given up over time. Do you ever get out kayaking anymore? I oftentimes feel like it's a shame that I never do a few things that I used to love, but then I go hiking and forget about them entirely again.

  4. I haven't been in a kayak since I co-led a trip on the Uppper Millers in April '08. However, I've kept all of my boats (3) and gear, because I know I'll be out there again. Just not in winter, any more!

  5. Greg – you have to hike to write, which is why I hike so much. But having no kids, does open up a lot more free time. Although I do know bloggers who post at soccer games. :-)

  6. The Fells are a true jewel. I live in Medford but I'm a transplant from NJ. People around there have no idea how lucky they are.

    The Long trail got me hooked on hiking too. I would love to get into winter hiking but the cost is a tough hurdle for me. I've been lurking in Ebay for cheap gear. :)

  7. Lol…oh yes, I hike to write as well! It is what feeds it.

    You can do it with kids, you just have to get them started from birth. That is how we have a 12 year old who didn't question us when young ;-)

  8. You can have kids and hike. You can follow Sarah's path and get them hooked early. Or you can get divorced and let the ex wife have the kids :)

  9. What other food source, besides goats, walks along with you? Oh don't get we started. I love kids…especially when they belong to someone else.

  10. This is a great story! I appreciated the part about having to choose direction. I have definitely been there and I bet most of the readers here have too.

  11. Steve in Ludlow MA

    The NY/NJ chapter? Do you know F.Zarb? I've hiked with those guys.

  12. yes, I know frank. last time I hiked with him was in Sages ravine in the Taconics.

  13. How did I not know you were a fiddler? Do you still fiddle?

    • No. I gave it up after realizing that I couldn’t learn by ear. I messed around a bit with a mandolin over the winter (playing by ear) but got to busy and didn’t stick with it. I haven’t sold my instruments though so there’s still hope I suppose.

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