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Classical Latin is a very artificial language, which both in prose and poetry favours complex constructions that to this day define what Western culture considers erudite sounding, intellectual speech. Because of this, it is hard to read, in a "pick up a book and read it" sort of way. This sentence from Cæsar is a typical, and by no means extreme example:

Ubi (Cæsar) se diutius duci intellexit et diem instare quo die frumentum militibus metiri oporteret, convocatis eorum principibus, quorum magnam copiam in castris habebat, in his Diviciaco et Lisco, qui summo magistratui præerat, quem vergobretum appellant Ædui, qui creatur annuus et vitæ necisque in suos habet potestatem, graviter eos accusat, quòd, quum neque emi neque ex agris sumi possit, tam necessario tempore, tam propinquis hostibus ab iis non sublevetur, præsertim quum magnâ ex parte eorum precibus adductus bellum susceperit, multo etiam graviùs quòd sit destitutus queritur.

That's from de Bello Gallico I.16, and you don't need to know any Latin to get my point: all that is one sentence! You need to keep a lot in your head to keep track of that many subordinate clauses, and that means that even with a perfect grasp of Latin grammar and vocabulary, you still need to read very attentively. And Cæsar is considered one of the easiest classical authors to read! (I'm told that some of Thucydides' sentences run over four pages.)

In contrast, a lot of the Latin written after the fall of Rome, mostly by monks, is a lot closer to the way we talk today. The Gesta Romanorum is exactly the kind of book you can just pick up and read once you know the basics of Latin grammar and vocab, but it's not considered appropriate to give to students because its style is so "barbarous" in comparison to the eloquent classicism of Cæsar and Cicero. (I really have to question that reasoning—it seems to me to be akin to giving King Lear to kindergarteners because Dr. Seuss' works lack literary merit—but that's an whole other article.)

This leaves students of Latin and Greek with a hurdle even greater than that of students in modern languages: not only do they have the same difficult leap from the textbook to the real thing, but the only "real thing" they come into contact with is exceedingly difficult in terms of its content!

Even though grammars, dictionaries, and introductions to Latin abound, there is still relatively little material that guides the beginner gradually yet expeditiously towards a confident mastery of classical material. For all too many aspirants, the leap (or toss) into the primary texts has entailed a falling into a kind of void: suddenly, the project slows down, often ending in a perpetual stall.

That quote comes from Claude Pavur at Saint Louis University, whose site takes one approach to the problem which you can read about there. While I don't doubt that his accelerated readers are a godsend to some, it's not a method that resonates with me. (In fairness, he's targetting the 'beginning intermediate' level whereas I probably fall closer to 'advanced intermediate'.) But I am in total agreement with him as to what the problem is:

Under such conditions, reading Latin becomes puzzle-solving, an adventure in decoding, a challenge to patience, a therapeutic escape in "busy work" — anything but an instructive and vital encounter with an interesting, complex, and vastly influential culture that often offers great writing, important ideas, valuable teachings, and significant personalities.

What I ended up doing back in university was instead turning to mediæval texts like the Gesta Romanorum that were easier to read, or less erudite Roman texts like the Passio Perpetuæ. They might not be the pinnacles of world literature that the canonical classics are, but at least I could have "an instructive and vital encounter with an interesting, complex, and vastly influential culture" through them. But I still moved like a snail through classical Latin, going to the dictionary with what seemed like every other word.

It so happens however that I recently stumbled across a fantastic new way to learn Classical Latin that makes getting across this hurdle so much easier. It came to me when I was looking for Ovid's Metamorphoses on Google Books, which has a huge selection of beautifully typeset Latin and Greek books printed in the XVIIIth and XIXth centuries (when, as I've already asserted, typesetting conventions were also superior to those of the present day). I found just what I was looking for: an 1821 edition of Ovid, beautifully typeset with js and ligatures. At first I noted with amusement that the explanatory notes, pointing out the meaning of difficult words or allusions, were themselves in Latin, which didn't seem very helpful on the editor's part! But as I started looking it over I discovered something even more amazing: in addition to the footnotes, each page has a paraphrase of the text in simple-to-understand Latin! After some assiduous searching, I was also able to find an even more copiously annotated edition of Virgil based on the same principle (this time with a Talmud-inspired page layout, no less). Here's an excerpt:

An intermediate-level student can usually understand the Interpretatio and Notæ on his own, but the poem itself would be too difficult without a lot of dictionary work. But with their help, he can understand the sense and context of the poem (all the while excercising his Latin skills), and so figure out how to read the verses all by himself.

This strikes me as such a brilliant way to bridge the gap between learning the basics of Latin and learning how to deal with the intricate literary complexity of the great classics. And the reader is never discouraged to be looking at the "interpretation", since it is still Latin after all: There's no shame in being told that tellus means terra—the reader will go on to discover the nuances on his own, and through his own experience, which is much better than just being told it and adding it to one's vocab list to memorize. (And if you don't recognise even the simple word in the paraphrase, then looking it up is only half the chore, because you know that when you do you will most likely learn two words in the process, since it is a priori the synonym of another word you don't know in the text itself.)

The effect of all this is that you no longer feel "I don't know Latin because I can't read pages of Virgil effortlessly"; instead you feel that "I can read Latin, but Virgil is a difficult author who takes some effort to tackle"—which after all is just what English students feel when dealing with Shakespeare or Milton for the first time. It's an important difference for the reader's self-confidence—and a more realistic acknowledgement of the difficulty of the great classics.

My own level in Latin was until recently stuck precisely in that rut between being able to read the Gesta Romanorum without ever picking up a dictionary, but feeling like an idiot when confronted with a page of Cicero (the goal of my recent Latin kick has been to at last rectify that). Now with these books I am really looking forward to "leveling up" on Virgil and Ovid, and bet I will progress twice as fast thanks to this brilliant, yet sadly no doubt long-forgotten, idea!