When I first started skating on the Minuteman, I tracked my progress with off-the-cuff estimates of distance entered on a spreadsheet. Fortunately someone soon explained the milepost markings to me and I used those with off-the-cuff estimates of fractional distances until gmap pedometer appeared around 2005. I switched from a spreadsheet at home to a spreadsheet in the cloud (which wasn't yet called that) when Google Docs arose.
[In case you're not familiar with them, the stone mile markers along the trail are marked in modified Roman numerals. Outbound they start with no mark at Alewife, then count I through X from East Arlington to Bedford Depot Park. Oddly, Bedford Depot says I on the facing-inbound side. The inbound marks count up to X in East Arlington, with nothing at Alewife where it could have said XI.]
This year I'm modernizing with a couple of activity tracking apps: Moves and MapMyFitness. These two have different aims, strengths, weaknesses, and bugs. I chose them with minimal research. If you read this post, you'll have done more research than I did.
Moves is a continuous activity tracker. You carry your phone, the phone records your location and movement, and Moves tries to figure out what you did. It's pretty good at figuring out whether you're walking, running, or riding in a car. It's not so good about bicycling, though it tries. (My ride on a Swan Boat in the Public Garden was recorded as cycling, no matter that the map showed me moving over water.) It doesn't even try to identify many other activities, including skating. The developers say that's no problem! You can edit an activity afterwards. And they'd be right except for one horrendous misfeature. Once Moves decides that some period of time is all one activity, you can't split it up. If I drive to a trail entrance ("Transport"), skate up and down the trail ("Transport"), then drive to my office ("Transport"), Moves calls that a single event. Several users have complained about this on Moves' Facebook page and gotten no reply. (I'm one of the complainers.) I reported this as a bug with the same result.
Another aspect of Moves is that it's now owned by Facebook. When that was announced, Moves swore that nothing would change and users' data was private. Two weeks later they changed their minds: your data might be available to "affiliates". If you worry where your personal data goes, there's your deal-breaker.
MapMyFitness (also MapMyRun, Ride, Walk, Hike) is for logging specific exercise events. You choose your activity, tap "Start Workout", and you're off. Potentially with your friends tracking you, if you enabled live tracking. Sharing and measurement are the major themes. The app records your location, distance, time, pace, split times, elevation -- and that's before you add optional hardware for pulse, . The MapMyX folks offer an inexpensive heart monitor which tells me that generic maximum heart rate formulas aren't much use.
Overall, the MapMy apps collect a pile of data for you, display it a few different ways, and offer to share it with your friends. I'd personally be happier with a more focused approach. I'm not interested in a pace vs. elevation chart and I'm skeptical of the app's calorie estimates. On the other hand, I might be fitter with a broader range of exercise, so a flexible app comes in handy.