The Long Trail is 275 miles long and runs from Massachusetts to Canada through the Green Mountains of Vermont. When I was 18, I decided to give this, my first long-distance hike a shot and headed out to hike the Long Trail starting at the Massachusetts border. It was my first time backpacking. It was my first time camping. It was my first time out in the woods by myself. I had no idea what I was doing.
I started the trail carrying 50+ lbs of nonsense in my pack including a sleeping bag that I have owned since I was 5 (that weighed a good 8 lbs but did nothing to keep me warm), heavy boots long past their expiration date, 2 trowels, 3 separate water purification systems (none of which I knew how to use) and a lot of other ridiculous-ness.
All of the mistakes I made on this trail were an important lesson. The trail beat me up pretty good but I learned a lot and the experience set me up to hike the Appalachian Trail the following year.