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I have always found the a- prefix to words (as in anew, ajar, aside, awake, afoot, a-hunting, etc.) fascinating. The NOAD says on this topic:

a- 2. prefix

•to; toward : aside | ashore.

• in a specified state or
manner : asleep | aloud.

• in the
process of (an activity) : a-hunting.

• on : afoot.

• in : nowadays.

ORIGIN
Old English , unstressed form of on.

a- 4. prefix

1 of: anew.

[ORIGIN: unstressed form of of ]

2 utterly: abash. [ORIGIN: from Anglo-Norman
French (corresponding to Old French
e-, es-), from Latin ex.]

While this gives quite a few examples, it leaves some areas of doubt to me:

1. At what time did this phenomenon happen?


2. It seem quite restricted to words of Saxon origin, as I don't see it used with words of Romance languages. Is that a consequence of point 1, or is it because usage wouldn't aggregate an Old English prefix with, e.g., a word of French origin?


3. Were there others words formed which haven't endured?


4. 
   Arguably subjective: I wonder how it came to pass that the same prefix is used with so many different meanings.

I don't think that it's the same prefix as much as it is the remnant of a number of different grammaticalised pre-fixings. Most of them seem to have happened during the period when then curious admixture of French, Viking Danish, Anglo-Saxon and a sprinkling of Gaelic were distilling themselves down into the various dialects of Middle English. The spelling's kind of arbitrary, but a is the letter we tend to use when a word starts with a schwa that's flatter than we'd represent with a short e.

English was essentially an unwritten language during that period (and the population essentially illiterate), so it could be a time of great flux. A lot of words were repartitioned. All one became alone, the n sound migrated from the ends of words like mine and thine to become the initial (and previously non-existent) consonant of words (especially eke names -- thine eke name also became thy nickname) and so on.

As with a lot of what happened during this period, what we have now in the language is mostly what was present in and around London when the orthography was fixed by printing. Many of the a- words that one recognises as quaint regionalisms today (like a-hunting) were standard in dialects that did not, themselves, have the good fortune to become the standard themselves.

As for new words, well, printing (and general literacy) sort of put a stop to arbitrary movement of word boundaries. A question was posted here earlier asking about the meaning of "grab a hold", and it didn't take long for somebody to reply that the phrase was actually "grab ahold" (something my spell checker has decided is a problem). I would bet that "grab a hold" or "take a hold" (hold being synonymous with handle, as preserved in hand-hold) was the original phrase. They sound the same, and if you hear a hold often enough without seeing it written down, there's no real reason why you might not think of them as a single word.

The prefix a- is present in native (derived from Old English) words where it commonly represent the Old English an (which means on): alive, asleep, abroad, ashore.
It can also be the Middle English of: anew, abreast (1590s).
It is a reduced form of the Old English past participle prefix ge- in words like aware, or the Old English intensifier, as in arise, awake, ashame.
In words from Romanic languages it usually represent the Latin ad (to, at).

_{[Source: Etymonline.]}

The "a-" prefix is a vestigial English grammatical form found in Anglo-Saxon, old English and even middle English (as well as old Jutish, old Saxon and old German). It is exclusively a Germanic thing.

The original form of this prefix was "Ʒe" (pronounced like "yuh"), so 'Ʒelic' became 'alike', for instance. It is often written as "ge-". This prefix was used quite liberally in old Germanic languages, and is still in use in modern German and modern dutch, despite its relative absence in all other modern Germanic languages - English included.

Here is the House on the Rock parable in Anglo-Saxon:

Ælc þara þe þas min word gehierþ, and þa wyrcþ, biþ gelic þæm wisan were, se his hus ofer stan getimbrode. Þa com þær regen and micel flod, and þær bleowan windas, and ahruron on þæt hus, and hit na ne feoll: soþlice hit wæs ofer stan getimbrod.

In just this example, you have the following words that use this prefix:

gehierþ (tr. a-heard)
gelic (tr. alike)
getimbrode (tr. a-built)
ahruron (gehruron) (tr. a-fell)
getimbrod

The prefix performs this function:

"The syllable ge- is used when some action or situation the word (verb) expresses has passed, is done, completed, being reported, being applied etc."

The “a-” is a weakened form of the preposition on or in, by the same verbal laziness that turned one into the article an, and then before consonants into a, pronounced “uh.” To go on board or on shore, to be in bed or on a slant, is to be aboard, ashore, abed, aslant, not to mention astern, abreast, ahead (originally nautical as well), afoot, aloof (on the luff side, to windward, steering clear), far afield, run aground. We don’t think of them as contractions of preposition + noun anymore, but many of our location and direction words have this form: afar, amid, atop, athwart, askew, awry, gone astray, and less obviously across, away, apart, around, aside, taken aback.

The same thing happened to time phrases. There’s a-nights and a-days, surviving in nowadays; in five dollars a day or twice a week, it looks like the “in” has been dropped from twice in a week, but actually it’s the article that disappeared. And sometimes these forms preserve old etymologies: aloft (“in the air”—German Luft), among (“in the crowd”—German Menge). Bonus points if you can spot the prepositional phrases in akin, anew, amiss, anon, aghast, agog.

Excerpt taken from: Fast Asleep and Wide Awake

January 27, 2015 | by Damion Searls