At first I wasn't crazy about hiking alone. I kept thinking about the what if's. It wasn't until I was at the summit of Algonquin and didn't have enough daylight to do Iroquois but decided to do it anyway that I started losing my fears. I came out in the dark and you know what? I wasn't afraid of hiking in the dark anymore (not sure why I was to begin with). After I thought through all the what if's I could think of, I wasn't afraid of hiking on my own anymore.
I'm sensible and have turned back more than once when I felt the conditions were unsafe (even 100 ft from the summit of Wright when it was icy with tremendous winds). I've always been able to calm myself down when a panicky feeling would arise and think through the situation.
I enjoy not having to meet people at a certain time and place, being able to choose my hike on the drive up or at the trailhead or at a trail junction, not worying if I'm hiking too fast or too slow, or if the other person has made plans after the hike, or if they're not going to want to go to the Black Bear at the Northway exit 26 after the hike for a bite to eat, etc.
I enjoy the solitude and lack of pressure of hiking alone. I also enjoy talking with people along the trail. I like being able to join people along the trail for a while if I want.
I don't have overnight gear yet but I won't have a problem backpacking alone either.
Btw, I won't hike below 20 degrees. It's just too darn cold. My glasses always fog up and freeze. For me, temperatures below 20 degree aren't very forgiving and a mistake could cost me my life. It's not worth it. It's not fun either!
I'll do popular trails in the winter alone. I'll hike popular "can't miss the trail" herd paths and trails in the warmer months alone. Other than that, I'll go with someone, preferably someone who knows the trail.
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