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So I realise this might not be a well defined question, but I hope it can still classify as not being a discussion.

So I have just finished highschool and after 6 years of Latin, I am not quite willing to give it up. I tried reading some texts by myself. Especially with Commentarii de bello gallico, I had some moderate succes in the first chapter as these parts were somewhat familiar as I had read simplied version of paragraphs here and there before, however I quickly ran into several problems which I also had with other texts.

My first problem is encountering a lot of unknown specific vocabulary, which really breaks the flow as I would need to look up a word every other sentence.

The second problem is that I am not entirely familiar with some less common expressions. Searching such expression is especially time consuming and breaks the flow of reading a lot.

So I think these problems are mainly due to the text being too difficult. So I wondered whether there are some easier Latin text out there or maybe text which is so well documented that if something unknown is encountered it can be quickly found.

I realise that reading with a translation next to the Latin is always an option, but I personally enjoy that less.

The best resource list I know of is this one from Justin Slocum Bailey of Indwelling Language. Check especially the section titled "Fairly simple Latin reading material."

Here I've selectively reproduced part of the list and added a few of my own recommendations. These resources are modern Latin readers designed to help students practice reading. They are not classic literary texts, though they often contain simplified versions. Most of these texts are easily found on Google Books, Archive.org, or a similar service simply by searching for the title.

• Chickering, First Latin Reader
  


• Miraglia, Fabulae Syrae
  


• Nutting, Ad Alpes
  


• Perry, Fabulae Romanae
  


• Ritchie, Fabulae Faciles
  

I also recommend the Legamus Transitional Reader series. These contain excerpts from classic Latin authors alongside extensive guidance. They simulate fairly well the experience of being in an intermediate level Latin course.

I've found I quite enjoy reading Ovid—his work is poetry, not prose, which adds a bit of difficulty, but the mythological subjects are pretty familiar, which makes it easier to deal with unknown words from context. And his style feels more transparent to me than e.g. Vergil's.

I usually translate with The Latin Library open in one window and Perseus's word study tool in another; if I'm stuck on a word, I just select and drag it from the Latin to Perseus, and it gives me not only a dictionary definition but also exactly which form this is.

The most important thing, though, is to just keep at it! Time and practice will make all of this easier, and this StackExchange is around for any weird grammar questions.

One slightly offbeat option would be Asterix. It's not quite classic literature, but it's well written and fun.

One option, perhaps best alongside other approaches, is to read (and listen to) the Latin news broadcast Nuntii Latini.
News come in every week and concern matters you have likely encountered in other media.
The texts are fairly short and aimed at a broad readership.

Unfortunately the vocabulary is not all that well documented.
The authors of Nuntii Latini cannot work entirely within classical Latin; new ideas often require new words.
The familiar context helps a lot with the vocabulary, though.

It is also easy to try: just go and try to read some, and you will get a feeling of its suitability to you.

A good place to start is at http://ephemeris.alcuinus.net/ This is a sort of newspaper with all kinds of contributions, from jokes and cartoons to serious current news items and fiction. It is edited by a Polish academic and is published from Warsaw.

The Latin isn't always perfect, because contributions are accepted from anyone with a basically sound competence, but it's generally easy enough for a beginner to follow. Since modern subjects are covered, the vocabulary is sometimes necessarily inventive, and even ingenious, but proper basic accidence and syntax are used.

Have a look. You'll probably enjoy it!

If you're so inclined, I'd suggest the Latin Bible. The syntax tends to be fairly straight-forward, and it's easy to consult English translations for comparison.

This may not be for everyone, but I personally read one articulus of the Summa Theologica by Thomas Aquinas every day. It can be found online at corpusthomisticum.org, and there is an English translation at CCEL.

Each articulus is nicely bite-sized, just the right thing over a cup of coffee. The structure is extremely regular and repetitive, which helps in concentrating on the language. The vocabulary does contain some technical philosophical terms, but not too many of those, and you soon pick them up. (I'd still recommend an introduction to scholastic philosophy, e.g., Edward Feser's books, like this one or that one.) Of course, this is not classical Latin, but medieval, which has a charm of its own. And you learn interesting things.