I pull 35' with a GMC 2500HD crew cab standard bed. Total length 55'. Only once did I get into a "what a have I done" situation. We wanted to stop at a restaurant that I knew we couldn't get into so I pulled in the shopping center next door. Every single parking lane had landscaping, curbs and narrow entries and exits at every turn. I ended up going over two curbs and had to back up several times to stay out of the bushes.
Never had trouble at campgrounds or gas stations as those are pretty easy to check out before you commit yourself.