Figured DIY Gear or General forum would be correct for my question.

Recommendations on easy to use trail mapping software?
I've never done mapping before, so more user friendly the better. Perks like adding icons and trail names are a must.

National Geographic software looks descent if you choose the right product to meet your needs.

This is the type of trail map I'm used to. I think it's a topo?:
http://http://www.mass.gov/dcr/parks/trails/Holyoke.gif
http://http://www.mass.gov/dcr/parks/trails/Mt-Tom.gif