Ok, I'd love to mention everything here, but that's not going to happen. New products pop up on the market all the time and I obviously can't cover those. I will try to cover a few of the older products that have been around awhile and will probably stay around awhile.
For machine based (meaning, the program is located on your computer) software, there are a few types. You've got programs that can put maps on your GPS, programs that can help you visualize your location, and programs that help you with training. I'm only covering the PC side, because that's what I use and know. I don't use a Mac, so I don't know anything about the Mac. Someone with experience there will have to write a topic about it.
First, software to put maps on your GPS.
For Garmin users, that has typically been Mapsource. There are some topographical map products and some street map products in the line. Garmin's street maps are your only option if you want autorouting. If you don't need/want that feature, you can use the free maps from www.gpsfiledepot.com or OpenStreetMaps. These free maps will be available to use if you use Mapsource. GPSFileDepot has good tutorials on how to do all kinds of stuff in order to use the maps available there. As far as I'm aware, there is no other way to install vector maps onto a Garmin GPS. If you want aerial photos (raster images) on your Garmin instead, you need to use MOAGU. It's not free, but it's also not expensive.
If you use a Magellan Triton, then National Geographic Topo! maps will transfer to the GPS. Simple as that. I don't know of any 3rd party options or free options, however. NG Topo! maps can get expensive, so be warned. Simple, but not cheap.
If you use a Delorme, it comes with Topo USA vector maps that will install to the GPS. For a subscription, you can download aerial photos and other basemaps from their service. If you splurge for XMap, you get more freedom about which maps to load...you can even use freely available ones (just search for the map type - topo, aerial, DRG, DOQQ, etc - and add your state to the search criteria. Every state has a different site).
Help beyond that on each individual program should be found in the program's help menu. But generally that's how you'd install maps onto your GPS. Make sure you check your GPS manual to make sure your GPS supports maps (some older ones do not) or whether you need to install a supplemental memory chip.
Now, to visualize your GPS tracks, there are a MULTITUDE of programs available. Old standbys include Garmin's Mapsource (basic, but not great), National Geographic Topo!, Delorme Topo USA, Google Earth, Topofusion, and many many more. The best I can suggest here is to look up each program to see if its features match your needs/wants. Each program has its strengths and weaknesses, but most should be able to at least download from your GPS no matter who made it (except Garmin Mapsource...it only supports Garmin receivers).
It's also worth noting that GPS Babel is a very useful little tool. It handles a huge variety of file formats and conversions. It can mean the world if you need to use a relatively obscure or proprietary format.
Also, MN DNR Garmin is useful for people with Garmin handhelds who do GIS work. It interfaces with your GPS and allows you to save your waypoints, tracks, or routes in the .shp format which is very common in GIS. This program is extremely useful for trail crews who might be working with city/county/state GIS staff and exchanging data.
To address folks who might want to do GIS work with their trail crew to map a new trail or an older system. Just a warning, there is a steep learning curve to GIS so if you dive in sight unseen, it'll be tough. That said, the best program for crews on a tight budget (read: no budget) is Quantum GIS, or QGIS. It's an open-source GIS package with plugins and relatively frequent updates. It's not perfect, though. It has limitations because the folks who develop it do so on their free time. A good, but not too expensive package is Manifold. Many licenses are available, so you can choose one that meets your cost/feature needs. Finally is ArcGIS. ArcGIS is essentially the industry standard, but is the most expensive option. Use this one if your budget is very big, or if you have access to a computer that already has it installed. Many of these programs can interface directly with many GPS receivers, or can interface with them if you have the plug-in for it. GPS Babel serves as a plugin for QGIS and MN DNR Garmin serves as a plugin for ArcGIS. Both programs can be used by themselves or as a plugin.
Now for training analysis. I'm pretty new to this area, but have tried a few things. Many offerings available are web services that tend to be fairly basic in nature since they tend towards sharing capabilities. The available PC software with serious analysis tools is limited. Garmin Training Center is a free option for Garmin users. Sporttracks is another option for users of other GPS receivers, however, Garmin has a good hold on the fitness GPS market at the moment. GTC is what it is...and relies on updates from Garmin for improvements. Sporttracks is 'donationware' so only costs what you want it to cost. However, Sporttracks has a pretty robust plugin system to add features. There are too many to go over here, but the list is fairly long. These programs also serve as basic visualization programs even though their main focus is fitness tracking.
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Thread: GPS Software (PC Based)