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Some of the better equipped wagons actually had a device on one of the wheel hub or axle that kept track of the number of revolutions of the wheel, and they knew x revolutions meant a mile, so they calculated from that.

The Mormons used this on their first trek across "The Mormon Trail" although as I recall the story. I'm under the impression they actually were the creators of that particular methodology.

Edit:

http://answers.google.com/answers/threadview?id=102978

On April 19, 1847, William Clayton, lead his wagon train from Omaha, Nebraska to Utah an in his journals he recorded his mileage. On this trip Clayton employed the use of a "roadometer" which was made of wooden cogs and gears that made use of the same rudimentary calculating methods that the later brass wheel odometer would use (you can see a reproduction of the original "Exodus Odometer" on the "Heritage Gateway" link below) .

The gateway link is dead, but the terms mentioned may turn up more via Google.

It's not an accurate measurement, but given this wasn't a government funded enterprise, I doubt anyone had access to more sophisticated method. And for those without an expensive pocket watch, they simply watched the sun passing by overhead.

Until the Mormons came up with the "roadometer" in 1847, it likely was an amalgam of different averages(and wildly varying degrees of accuracy). They knew roughly what "the average _____" could do in certain circumstances, so based on that(and the matter that caravans move at the speed of the slowest member) they could "make an educated guess" on ground covered in general.

More specifically however, there were "trail guides" with landmarks, and those landmarks had (roughly) known travel distances between them. So while they might not know total distance traveled in a given day. They would know when they passed Chimney Rock and when they reached Independence Rock. At which point they could come up with an "average day's travel" based on the distance traveled and time taken.

A group with an in-person guide rather than a printing of dubious origins would be likely to have other more numerous guide points to use. As to how those distances were determined? Who knows? Might have been some random guy with a sextant and pocket watch, or maybe someone with more formal training in surveying.

More often than not, they probably made a educated guess based on prodigy to various landmarks they were aware of. Obviously, someone with "local knowledge" would be better at such guesswork. Unless they had a roadometer, of course.

As to how those distances were determined? Who knows? Might have been some random guy with a sextant and pocket watch, or maybe someone with more formal training in surveying.

They were most likely determined by the BLM's Public Land Survey System which goes all the way back to 1785 and used / uses professional surveyors.

https://nationalmap.gov/small_scale/a_plss.html#two

Those surveys didn't get into much of the western interior until much later. Haven't looked, but wouldn't be surprised to find the first government surveys probably didn't happen until either the railroads came through, or active settlement was happening nearby. In other words, much of the Oregon Trail went unsurveyed by the government until sometime in the 1850's or later.

This would also be consistent with the exact route and other details being unknown today. Something which a proper survey in that time frame would have likely resolved or outright prevented. For example, there are at least a couple "landmark" forts along the trail which nobody knows the location of today(and a few others had multiple locations over the years--Forts Bridger and Boise come to mind; but their sites are known). Granted, the likely location of one is suspected of being in a reservoir today(making it hard to dig up intentionally or otherwise locate), but those are things which did happen.

Oh, it's worse than that! If you didn't go to High School in Ohio or Michigan, you might not know about this:

There's a Fort in New England that the Americans thought they'd built on their side of the border. Only to later discover it was in Canada during some subsequent negotiations (where the borders were surveyed again) regarding borders. Needless to say, after all was said an done, the Yanks kept their fort(presumably at the cost of land elsewhere) and acquired territorial rights to that land.

There's a Fort in New England that the Americans thought they'd built on their side of the border. Only to later discover it was in Canada during some subsequent negotiations (where the borders were surveyed again) regarding borders. Needless to say, after all was said an done, the Yanks kept their fort(presumably at the cost of land elsewhere) and acquired territorial rights to that land.

"Fort Blunder", at the northern end of Lake Champlain. When they realized that it was actually in Canada, construction was aborted and the site abandoned, and a new fort (Fort Montgomery) was constructed on the right side of the border. No actual shifting of borders occurred.

https://en.wikipedia.org/wiki/Fort_Montgomery_(Lake_Champlain)

The people actually doing the travel were usually more concerned about the time taken to reach known locations or landmarks than the actual distance covered. However, they did know how much they usually expected to travel each day because it was known how fast the animals travelled.

And this goes doubly so for wagon trains where shortest distance may not be fastest route. Often it was faster/safer to go around the mountain rather than go over that 7+% mountain grade.

However, let me be a little more specific. Do we believe that people crossing huge expanses were actually thinking in terms of miles back then.

Well, as already mentioned, if they were Mormon, there is a decent chance they were, and had a reliable means to do so. Everyone else? Depends on the year, where they are(and available landmarks), and a number of other things. Which isn't to mention the matter of "which mile?"

More often than not, I think you would find "most people" would often be speaking of distance as a measure of time rather than actual distance. So you'll hear what the expected travel time is rather than distance, although an approximation of that may be given as well.

Not settler trains, but some of the longer official survey groups who went with several wagons used to do that. Most survey groups went by horse with pack mules.

With the tend of thousands of people that migrated. It is a reasonable assumption that a few wagon trains had a surveyor among their number. Certainly more of an exception than the rule, but it's probable that it happened.

This is not a new technique.

So "not new" that it's literally where the word "mile" comes from. It's derived from Latin mille passus, "a thousand paces". The Roman legions would measure distances overland by counting paces as they marched. Every thousandth time the left foot hits the ground, you set a milestone.

The irony of this is that when I lived in San Antonio I commuted about 14.7 miles each way from my house to my office building... 20-25 minutes in heavy commute time traffic. And that same mileage was what a good ox team would be able to haul a Conestoga in a full day of travel.

To be fair to the ox team, if they were pulling wagons across the kind of roads we have now, they'd be likely to do a lot better than 11 to 12 miles in a day. The even and consistent surface alone would probably add several miles to their day, and that's without manipulating the road grades.

Also, I would strongly suspect a number of journals from that time are available online, it is just finding the right place to look. I strongly suspect the LDS Church, by way of BYU probably, has a number of such journals in some kind of digital and public form.

I dunno. Oxen are not known for speed.

Not having to work against ruts, low spots in the dirt/mud (potholes would still be a pain for them, but at their speed, also possible to avoid, and probably shallower than what they frequently encountered.

Fact is that "level ground" for a wagon train usually wasn't very level. It also was a contributor to the first railroads being built, so that the mules/other beasts of burden would have a consistent surface to work with. Yes, there were railroads before there were steam powered locomotives. They just happened to exist in a narrow window of time between both iron being available in the quantity needed to build them and the means needed to do so, and the additional advent of the locomotive.

Oxen are not known for speed.

Even without roads, good bridges over the streams and rivers along the way likely would save several days for a wagon train.