Was out doing some long range practice a couple of years ago and ran into some sketchy folks that seemed pretty concerned we were where we were--on private timberland. They were asking questions of my daughter like, "How often do you guys come up here?", etc., which I didn't hear until I asked my daughter what they'd said. Hmm... My normal radar didn't get up and running quite as fast as it does in town and afterwards I had the realization from several indications that these folks were likely druggies and probably were either looking for a place or had some type of operation going on up there.
Have had a couple (of many close bear encounters) spooky bear encounters over the years where you started to wonder if you were on the menu. One time it seemed pretty clear we were. Went into dense cover 3x last year after shot bears with pistol drawn in places a rifle just wouldn't fit well, etc. etc. I often have long shots that then I don't want to carry a 12-13 lb long range rifle down to the animal 600-800 vertical feet down and whatever distance, etc. and back up. A decent sidearm is nice to have--and I'm an ounce counter!
You guys that don't carry buy insurance don't you? But, you'll never need it, right?
If I'm with someone else all the time, each with a rifle, I usually don't carry while hunting (pistol back at camp), but if by myself I usually carry but mostly for the reason mentioned above of not wanting to expend the energy to pack a heavy rifle down a long ways and back up, with a full load of meat (last time I did that, I had 130 lb load and finally figured there has got to be a better way) etc. to retrieve game if I don't have to. Sometimes the retrieving and processing occurs in the dark with rifle to side...how far away?...and not immediately accessible. Will never forget one time solo back in the wilderness working on a deer in a high mountain meadow at night, shining the headlamp around and seeing several sets of eyes looking back at me from multiple angles. I'm sure they were all deer just feeding into the meadow at night, but it was a little spooky. And, my 13 lb rifle was a few feet away and I'm known bear country.
Right now, if I was to buy only one gun for combo town and woods, it would be a Glock G20 in 10mm. Most 10mm commercial self-defense loads for it are essentially .40 SW loads so use those in town, but for woods carry, you can seriously up the power factor and using 200g hardcast and 200g expanding bullets, etc. have a potent load with 15+1 capacity. Pretty versatile pistol in that regard. Glock says don't shoot hardcast in their barrels, but you can buy an aftermarket barrel where that's not an issue. I put a KKM barrel in my G40 which is my goto woods gun if hunting bears, general hiking or in griz country.