I have had a fair amount of experience with the eTrex Legend. I wish I had one when I live North of Sexsmith, Alberta. In those days the bush was rather dense.
Garmin’s Map Source software will do what you want. I recommend that you buy Garmin MapSource Topo Canada Software. You can transfer maps, waypoints, and tracks with it.
http://www.amazon.com/Garmin-TOPO-Topographical-Maps-Canada/dp/B0006ZSW0E/ref=sr_1_1?s=software&ie=UTF8&qid=1278308527&sr=1-1Check the reviews.
https://buy.garmin.com/shop/shop.do?pID=1016&pvID=2303#coverageTabThis is the new version. I do not know if it will work on your unit.
I do not believe Garmin’s Trip & Waypoint Manager shipped with the units you purchased. The map is very general and you cannot transfer maps with this product. It does have some road numbers such as 590, 42, and 805 as examples.
http://www.tigergps.com/gamatrandwam.htmlMy assumption is that you are looking at getting out and back from the bush and this not for you next trip to Calgary?
You can also buy the mapping software that is installed in you Nuvi.
If I was heading for Canada with the software in my automotive gps, I would load my handhelds the Canada Topo software. Note that I have pointed you towards an older version, it cost less, and most likely it is compatible with your older Legend and you can load 8MB of maps to it from the software. The newer version does not list itself as being compatibly with the older Legend. If you want the newer version I suggest you call Garmin support to insure it works with your unit. It is not on the list.
US: 913-397-8200
US Toll Free: 1-800-800-1020
Canada: 1-866-429-9296
The other catch in the system could be your computer. What operating system does it have?